General Information

Computed Descriptors

Download SDF
2D Structure
CID445354
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
InChIInChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChI KeyFPIPGXGPPPQFEQ-OVSJKPMPSA-N
Canonical SMILESCC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
Molecular FormulaC20H30O
Wikipediaretinol

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight286.459
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count5
Complexity496.0
CACTVS Substructure Key Fingerprint A A A D c e B 4 I A A A A A A A A A A A A A A A A A A A A A A A A A A g A A A A A A A A A A A A A A A A G g A A C A A A D g C g g A I C A A A A A g C A A i B C A A A A A A A g A A A I C A A A A A g I F A I A A Q A A E A A A g A A I k A M A g M A P A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area20.2
Monoisotopic Mass286.23
Exact Mass286.23
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem


Food Additives Biosynthesis/Degradation


ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9665
Human Intestinal AbsorptionHIA+0.9938
Caco-2 PermeabilityCaco2+0.7272
P-glycoprotein SubstrateNon-substrate0.5939
P-glycoprotein InhibitorNon-inhibitor0.8205
Non-inhibitor0.5631
Renal Organic Cation TransporterNon-inhibitor0.7646
Distribution
Subcellular localizationLysosome0.8110
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8193
CYP450 2D6 SubstrateNon-substrate0.8324
CYP450 3A4 SubstrateSubstrate0.5522
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9230
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.8420
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7388
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8563
Non-inhibitor0.8853
AMES ToxicityAMES toxic0.6952
CarcinogensNon-carcinogens0.7004
Fish ToxicityHigh FHMT0.8649
Tetrahymena Pyriformis ToxicityHigh TPT0.9884
Honey Bee ToxicityHigh HBT0.8263
BiodegradationReady biodegradable0.5504
Acute Oral ToxicityIII0.8739
Carcinogenicity (Three-class)Non-required0.6196

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-2.8144LogS
Caco-2 Permeability1.6607LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1249LD50, mol/kg
Fish Toxicity0.5928pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.9025pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of ExposureOral, readily absorbed from the normal gastrointestinal tract
Mechanism of ToxicityVision:Vitamin A (all-<i>trans</i> retinol) is converted in the retina to the 11-<i>cis</i>-isomer of retinaldehyde or 11-<i>cis</i>-retinal. 11-<i>cis</i>-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-<i>cis</i>-retinal, while attached to opsin in rhodopsin is isomerized to all-<i>trans</i>-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-<i>trans</i>-retinal is then released from opsin and reduced to all-<i>trans</i>-retinol. All-<i>trans</i>-retinol is isomerized to 11-<i>cis</i>-retinol in the dark, and then oxidized to 11-<i>cis</i>-retinal. 11-<i>cis</i>-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-<i>cis</i> retinal rapidly. <br/>Epithelial differentiation: The role of Vitamin A in epithelial differentiation, as well as in other physiological processes, involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARs; and retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.
MetabolismHepatic. Retinol is conjugated with glucuronic acid; the B-glucuronide undergoes enterohepatic circulation and oxidation to retinol and retinoic acid. Retinoic acid undergoes decarboxylation and conjugation with glucuronic acid. Half Life: 1.9 hours
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsNone
TreatmentThe treatment of hypervitaminosis A consists of immediate withdrawal of the vitamin along with symptomatic and supportive treatment.
Reference
  1. Roncone DP: Xerophthalmia secondary to alcohol-induced malnutrition. Optometry. 2006 Mar;77(3):124-33.[16513513 ]
  2. Norum KR, Blomhoff R: McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage. Am J Clin Nutr. 1992 Oct;56(4):735-44.[1414975 ]
  3. Graham-Maar RC, Schall JI, Stettler N, Zemel BS, Stallings VA: Elevated vitamin A intake and serum retinol in preadolescent children with cystic fibrosis. Am J Clin Nutr. 2006 Jul;84(1):174-82.[16825693 ]
  4. Sorenson AW, Delhumeau C, Bernstein MS, Costanza MC, Morabia A: Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000. Eur J Clin Nutr. 2003 Jan;57(1):177-85.[12548314 ]
  5. Alberts D, Ranger-Moore J, Einspahr J, Saboda K, Bozzo P, Liu Y, Xu XC, Lotan R, Warneke J, Salasche S, Stratton S, Levine N, Goldman R, Islas M, Duckett L, Thompson D, Bartels P, Foote J: Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin. Clin Cancer Res. 2004 Mar 15;10(6):1875-80.[15041701 ]
  6. Wieringa FT, Dijkhuizen MA, West CE, Thurnham DI, Muhilal, Van der Meer JW: Redistribution of vitamin A after iron supplementation in Indonesian infants. Am J Clin Nutr. 2003 Mar;77(3):651-7.[12600856 ]
  7. Egeland GM, Berti P, Soueida R, Arbour LT, Receveur O, Kuhnlein HV: Age differences in vitamin A intake among Canadian Inuit. Can J Public Health. 2004 Nov-Dec;95(6):465-9.[15622799 ]
  8. Ribaya-Mercado JD, Solon FS, Fermin LS, Perfecto CS, Solon JA, Dolnikowski GG, Russell RM: Dietary vitamin A intakes of Filipino elders with adequate or low liver vitamin A concentrations as assessed by the deuterated-retinol-dilution method: implications for dietary requirements. Am J Clin Nutr. 2004 Apr;79(4):633-41.[15051608 ]
  9. Kieu NT, Yurie K, Hung NT, Yamamoto S, Chuyen NV: Simultaneous analysis of retinol, beta-carotene and tocopherol levels in serum of Vietnamese populations with different incomes. Asia Pac J Clin Nutr. 2002;11(2):92-7.[12074187 ]
  10. Torma H, Vahlquist A: Vitamin A esterification in human epidermis: a relation to keratinocyte differentiation. J Invest Dermatol. 1990 Jan;94(1):132-8.[2295828 ]
  11. Allen LH, Haskell M: Estimating the potential for vitamin A toxicity in women and young children. J Nutr. 2002 Sep;132(9 Suppl):2907S-2919S.[12221269 ]
  12. Ribaya-Mercado JD, Solomons NW, Medrano Y, Bulux J, Dolnikowski GG, Russell RM, Wallace CB: Use of the deuterated-retinol-dilution technique to monitor the vitamin A status of Nicaraguan schoolchildren 1 y after initiation of the Nicaraguan national program of sugar fortification with vitamin A. Am J Clin Nutr. 2004 Nov;80(5):1291-8.[15531678 ]
  13. Marquez M, Yepez CE, Sutil-Naranjo R, Rincon M: [Basic aspects and measurement of the antioxidant vitamins A and E]. Invest Clin. 2002 Sep;43(3):191-204.[12229281 ]
  14. Mills JP, Penniston KL, Tanumihardjo SA: Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. Int J Vitam Nutr Res. 2005 Mar;75(2):126-32.[15929633 ]
  15. Penniston KL, Tanumihardjo SA: The acute and chronic toxic effects of vitamin A. Am J Clin Nutr. 2006 Feb;83(2):191-201.[16469975 ]
  16. Jumpsen JA, Brown NE, Thomson AB, Paul Man SF, Goh YK, Ma D, Clandinin MT: Fatty acids in blood and intestine following docosahexaenoic acid supplementation in adults with cystic fibrosis. J Cyst Fibros. 2006 May;5(2):77-84. Epub 2006 Feb 28.[16507353 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassRetinoids
Intermediate Tree NodesNot available
Direct ParentRetinoids
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsRetinoid skeleton - Diterpenoid - Fatty alcohol - Fatty acyl - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

From ClassyFire


Targets

General Function:
Retinol transporter activity
Specific Function:
Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
Gene Name:
RBP4
Uniprot ID:
P02753
Molecular Weight:
23009.8 Da
References
  1. Isken A, Golczak M, Oberhauser V, Hunzelmann S, Driever W, Imanishi Y, Palczewski K, von Lintig J: RBP4 disrupts vitamin A uptake homeostasis in a STRA6-deficient animal model for Matthew-Wood syndrome. Cell Metab. 2008 Mar;7(3):258-68. doi: 10.1016/j.cmet.2008.01.009. [18316031 ]
General Function:
Retinol dehydrogenase activity
Specific Function:
Stereospecific 11-cis retinol dehydrogenase, which catalyzes the final step in the biosynthesis of 11-cis retinaldehyde, the universal chromophore of visual pigments. Also able to oxidize 9-cis-retinol and 13-cis-retinol, but not all-trans-retinol. Active in the presence of NAD as cofactor but not in the presence of NADP.
Gene Name:
RDH5
Uniprot ID:
Q92781
Molecular Weight:
34978.425 Da
References
  1. Belyaeva OV, Kedishvili NY: Comparative genomic and phylogenetic analysis of short-chain dehydrogenases/reductases with dual retinol/sterol substrate specificity. Genomics. 2006 Dec;88(6):820-30. Epub 2006 Jul 24. [16860536 ]
General Function:
Retinal dehydrogenase activity
Specific Function:
Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
Gene Name:
ALDH1A1
Uniprot ID:
P00352
Molecular Weight:
54861.44 Da
References
  1. Huq MD, Tsai NP, Gupta P, Wei LN: Regulation of retinal dehydrogenases and retinoic acid synthesis by cholesterol metabolites. EMBO J. 2006 Jul 12;25(13):3203-13. Epub 2006 Jun 8. [16763553 ]
General Function:
Retinal dehydrogenase activity
Specific Function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
Gene Name:
ALDH1A2
Uniprot ID:
O94788
Molecular Weight:
56723.495 Da
References
  1. Nakazawa N, Montedonico S, Takayasu H, Paradisi F, Puri P: Disturbance of retinol transportation causes nitrofen-induced hypoplastic lung. J Pediatr Surg. 2007 Feb;42(2):345-9. [17270546 ]
General Function:
Retinol dehydrogenase activity
Specific Function:
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinal to all-trans-retinol. May play a role in the regeneration of visual pigment at high light intensity (By similarity).
Gene Name:
RDH8
Uniprot ID:
Q9NYR8
Molecular Weight:
33755.02 Da
References
  1. Fishman GA, Roberts MF, Derlacki DJ, Grimsby JL, Yamamoto H, Sharon D, Nishiguchi KM, Dryja TP: Novel mutations in the cellular retinaldehyde-binding protein gene (RLBP1) associated with retinitis punctata albescens: evidence of interfamilial genetic heterogeneity and fundus changes in heterozygotes. Arch Ophthalmol. 2004 Jan;122(1):70-5. [14718298 ]
General Function:
Transporter activity
Specific Function:
Intracellular transport of retinol.
Gene Name:
RBP1
Uniprot ID:
P09455
Molecular Weight:
15850.13 Da
References
  1. Folli C, Viglione S, Busconi M, Berni R: Biochemical basis for retinol deficiency induced by the I41N and G75D mutations in human plasma retinol-binding protein. Biochem Biophys Res Commun. 2005 Nov 4;336(4):1017-22. [16157297 ]
General Function:
Serine-type peptidase activity
Specific Function:
IRBP shuttles 11-cis and all trans retinoids between the retinol isomerase in the pigment epithelium and the visual pigments in the photoreceptor cells of the retina.
Gene Name:
RBP3
Uniprot ID:
P10745
Molecular Weight:
135361.46 Da
References
  1. Salvador-Silva M, Ghosh S, Bertazolli-Filho R, Boatright JH, Nickerson JM, Garwin GG, Saari JC, Coca-Prados M: Retinoid processing proteins in the ocular ciliary epithelium. Mol Vis. 2005 May 18;11:356-65. [15928609 ]
General Function:
Retinol dehydrogenase activity
Specific Function:
Catalyzes the reduction of all-trans-retinal to all-trans-retinol in the presence of NADPH.
Gene Name:
DHRS3
Uniprot ID:
O75911
Molecular Weight:
33548.115 Da
References
  1. Chai Z, Brereton P, Suzuki T, Sasano H, Obeyesekere V, Escher G, Saffery R, Fuller P, Enriquez C, Krozowski Z: 17 beta-hydroxysteroid dehydrogenase type XI localizes to human steroidogenic cells. Endocrinology. 2003 May;144(5):2084-91. [12697717 ]
General Function:
Thyroid hormone binding
Specific Function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular Weight:
56107.995 Da
References
  1. Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [15950969 ]
General Function:
Transporter activity
Specific Function:
Soluble retinoid carrier essential the proper function of both rod and cone photoreceptors. Participates in the regeneration of active 11-cis-retinol and 11-cis-retinaldehyde, from the inactive 11-trans products of the rhodopsin photocycle and in the de novo synthesis of these retinoids from 11-trans metabolic precursors. The cycling of retinoids between photoreceptor and adjacent pigment epithelium cells is known as the 'visual cycle'.
Gene Name:
RLBP1
Uniprot ID:
P12271
Molecular Weight:
36474.02 Da
References
  1. Vogel JS, Bullen EC, Teygong CL, Howard EW: Identification of the RLBP1 gene promoter. Invest Ophthalmol Vis Sci. 2007 Aug;48(8):3872-7. [17652763 ]
General Function:
Transporter activity
Specific Function:
Intracellular transport of retinol.
Gene Name:
RBP7
Uniprot ID:
Q96R05
Molecular Weight:
15535.585 Da
References
  1. Caprioli A, Zhu H, Sato TN: CRBP-III:lacZ expression pattern reveals a novel heterogeneity of vascular endothelial cells. Genesis. 2004 Nov;40(3):139-45. [15493015 ]
General Function:
Retinol dehydrogenase activity
Specific Function:
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity toward 9-cis and all-trans-retinol. Also involved in the metabolism of short-chain aldehydes. No steroid dehydrogenase activity detected. Might be the key enzyme in the formation of 11-cis-retinal from 11-cis-retinol during regeneration of the cone visual pigments.
Gene Name:
RDH12
Uniprot ID:
Q96NR8
Molecular Weight:
35093.455 Da
References
  1. Thompson DA, Janecke AR, Lange J, Feathers KL, Hubner CA, McHenry CL, Stockton DW, Rammesmayer G, Lupski JR, Antinolo G, Ayuso C, Baiget M, Gouras P, Heckenlively JR, den Hollander A, Jacobson SG, Lewis RA, Sieving PA, Wissinger B, Yzer S, Zrenner E, Utermann G, Gal A: Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle. Hum Mol Genet. 2005 Dec 15;14(24):3865-75. Epub 2005 Nov 3. [16269441 ]
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Gene Name:
LRAT
Uniprot ID:
O95237
Molecular Weight:
25702.635 Da
References
  1. Liu L, Gudas LJ: Disruption of the lecithin:retinol acyltransferase gene makes mice more susceptible to vitamin A deficiency. J Biol Chem. 2005 Dec 2;280(48):40226-34. Epub 2005 Sep 20. [16174770 ]
General Function:
Alcohol dehydrogenase (nadp+) activity
Specific Function:
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity toward 9-cis and all-trans-retinol. No steroid dehydrogenase activity detected.
Gene Name:
RDH14
Uniprot ID:
Q9HBH5
Molecular Weight:
36864.355 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General Function:
Oxidoreductase activity
Specific Function:
Retinol saturase carrying out the saturation of the 13-14 double bond of all-trans-retinol to produce all-trans-13,14-dihydroretinol. Has activity toward all-trans-retinol as substrate. Does not use all-trans-retinoic acid nor 9-cis, 11-cis or 13-cis-retinol isomers as substrates. May play a role in the metabolism of vitamin A (By similarity).
Gene Name:
RETSAT
Uniprot ID:
Q6NUM9
Molecular Weight:
66818.935 Da
References
  1. Moise AR, Isken A, Dominguez M, de Lera AR, von Lintig J, Palczewski K: Specificity of zebrafish retinol saturase: formation of all-trans-13,14-dihydroretinol and all-trans-7,8- dihydroretinol. Biochemistry. 2007 Feb 20;46(7):1811-20. Epub 2007 Jan 25. [17253779 ]
General Function:
Lipid transporter activity
Specific Function:
APOD occurs in the macromolecular complex with lecithin-cholesterol acyltransferase. It is probably involved in the transport and binding of bilin. Appears to be able to transport a variety of ligands in a number of different contexts.
Gene Name:
APOD
Uniprot ID:
P05090
Molecular Weight:
21275.37 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [16461020 ]
General Function:
Receptor binding
Specific Function:
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
Gene Name:
DHRS4
Uniprot ID:
Q9BTZ2
Molecular Weight:
29536.885 Da
References
  1. Du K, Liu GF, Xie JP, Song XH, Li R, Liang B, Huang DY: A 27.368 kDa retinal reductase in New Zealand white rabbit liver cytosol encoded by the peroxisomal retinol dehydrogenase-reductase cDNA: purification and characterization of the enzyme. Biochem Cell Biol. 2007 Apr;85(2):209-17. [17534402 ]
General Function:
Transporter activity
Specific Function:
Catalyzes the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation. Involved in a variety of CNS functions, such as sedation, NREM sleep and PGE2-induced allodynia, and may have an anti-apoptotic role in oligodendrocytes. Binds small non-substrate lipophilic molecules, including biliverdin, bilirubin, retinal, retinoic acid and thyroid hormone, and may act as a scavenger for harmful hydrophopic molecules and as a secretory retinoid and thyroid hormone transporter. Possibly involved in development and maintenance of the blood-brain, blood-retina, blood-aqueous humor and blood-testis barrier. It is likely to play important roles in both maturation and maintenance of the central nervous system and male reproductive system.
Gene Name:
PTGDS
Uniprot ID:
P41222
Molecular Weight:
21028.665 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [16461020 ]
General Function:
Retinol dehydrogenase activity
Specific Function:
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity towards 9-cis and all-trans-retinol. Also involved in the metabolism of short-chain aldehydes. No steroid dehydrogenase activity detected.
Gene Name:
RDH11
Uniprot ID:
Q8TC12
Molecular Weight:
35385.955 Da
References
  1. Gallego O, Belyaeva OV, Porte S, Ruiz FX, Stetsenko AV, Shabrova EV, Kostereva NV, Farres J, Pares X, Kedishvili NY: Comparative functional analysis of human medium-chain dehydrogenases, short-chain dehydrogenases/reductases and aldo-keto reductases with retinoids. Biochem J. 2006 Oct 1;399(1):101-9. [16787387 ]
General Function:
Oxidoreductase activity
Specific Function:
Does not exhibit retinol dehydrogenase (RDH) activity in vitro.
Gene Name:
RDH13
Uniprot ID:
Q8NBN7
Molecular Weight:
35931.85 Da
References
  1. Keller B, Adamski J: RDH12, a retinol dehydrogenase causing Leber's congenital amaurosis, is also involved in steroid metabolism. J Steroid Biochem Mol Biol. 2007 May;104(3-5):190-4. Epub 2007 Mar 23. [17512723 ]
General Function:
Transporter activity
Specific Function:
Intracellular transport of retinol.
Gene Name:
RBP2
Uniprot ID:
P50120
Molecular Weight:
15706.595 Da
References
  1. Suruga K, Kitagawa M, Yasutake H, Takase S, Goda T: Diet-related variation in cellular retinol-binding protein type II gene expression in rat jejunum. Br J Nutr. 2005 Dec;94(6):890-5. [16351764 ]
General Function:
Transporter activity
Specific Function:
Intracellular transport of retinol.
Gene Name:
RBP5
Uniprot ID:
P82980
Molecular Weight:
15931.17 Da
References
  1. O'Byrne SM, Wongsiriroj N, Libien J, Vogel S, Goldberg IJ, Baehr W, Palczewski K, Blaner WS: Retinoid absorption and storage is impaired in mice lacking lecithin:retinol acyltransferase (LRAT). J Biol Chem. 2005 Oct 21;280(42):35647-57. Epub 2005 Aug 22. [16115871 ]
General Function:
Zinc ion binding
Specific Function:
Transcriptional regulator which is important for the differentiation and maintenance of meso-diencephalic dopaminergic (mdDA) neurons during development. It is crucial for expression of a set of genes such as SLC6A3, SLC18A2, TH and DRD2 which are essential for development of mdDA neurons (By similarity).
Gene Name:
NR4A2
Uniprot ID:
P43354
Molecular Weight:
66590.375 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Specific Function:
Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
Gene Name:
FBF1
Uniprot ID:
Q8TES7
Molecular Weight:
125445.19 Da
References
  1. N'soukpoe-Kossi CN, Sedaghat-Herati R, Ragi C, Hotchandani S, Tajmir-Riahi HA: Retinol and retinoic acid bind human serum albumin: stability and structural features. Int J Biol Macromol. 2007 Apr 10;40(5):484-90. Epub 2006 Nov 24. [17184834 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
Gene Name:
RARA
Uniprot ID:
P10276
Molecular Weight:
50770.805 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 (By similarity). Specifically binds 9-cis retinoic acid (9C-RA).
Gene Name:
RXRB
Uniprot ID:
P28702
Molecular Weight:
56921.38 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXRs is 9-cis retinoic acid. RXRA serves as a common heterodimeric partner for a number of nuclear receptors. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. The RXRA/PPARA heterodimer is required for PPARA transcriptional activity on fatty acid oxidation genes such as ACOX1 and the P450 system genes.
Gene Name:
RXRA
Uniprot ID:
P19793
Molecular Weight:
50810.835 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
Gene Name:
VDR
Uniprot ID:
P11473
Molecular Weight:
48288.64 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Protein homodimerization activity
Specific Function:
Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the conjugation of glutathione with a wide range of aryl halides and organic isothiocyanates. Also exhibits low glutathione-peroxidase activity towards cumene hydroperoxide.
Gene Name:
HPGDS
Uniprot ID:
O60760
Molecular Weight:
23343.65 Da

From T3DB