General Information

MaintermSEBACIC ACID
CAS Reg.No.(or other ID)111-20-6
Regnum 175.105
175.300
175.320
177.1200
177.1500
177.1630
177.1390
177.2420

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID5192
IUPAC Namedecanedioic acid
InChIInChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
InChI KeyCXMXRPHRNRROMY-UHFFFAOYSA-N
Canonical SMILESC(CCCCC(=O)O)CCCC(=O)O
Molecular FormulaC10H18O4
Wikipediasebacic acid

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight202.25
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Complexity157.0
CACTVS Substructure Key Fingerprint A A A D c e B w O 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 A A A A A A A A A A A A A G g A A C A A A C A C A g A A A C A A A A g A I A A C Q C A A A A A A A A A A A A A E A A A A A A B I A A A A A Q A A E A A A A A A G I y K C 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 A = =
Topological Polar Surface Area74.6
Monoisotopic Mass202.121
Exact Mass202.121
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
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+0.7397
Human Intestinal AbsorptionHIA+0.5731
Caco-2 PermeabilityCaco2-0.6412
P-glycoprotein SubstrateNon-substrate0.6969
P-glycoprotein InhibitorNon-inhibitor0.9845
Non-inhibitor0.9229
Renal Organic Cation TransporterNon-inhibitor0.9359
Distribution
Subcellular localizationMitochondria0.8984
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8447
CYP450 2D6 SubstrateNon-substrate0.9050
CYP450 3A4 SubstrateNon-substrate0.7534
CYP450 1A2 InhibitorNon-inhibitor0.9046
CYP450 2C9 InhibitorNon-inhibitor0.9390
CYP450 2D6 InhibitorNon-inhibitor0.9729
CYP450 2C19 InhibitorNon-inhibitor0.9762
CYP450 3A4 InhibitorNon-inhibitor0.9600
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9927
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9348
Non-inhibitor0.9602
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.8382
Fish ToxicityHigh FHMT0.8783
Tetrahymena Pyriformis ToxicityHigh TPT0.6559
Honey Bee ToxicityHigh HBT0.6229
BiodegradationReady biodegradable0.8506
Acute Oral ToxicityIV0.6448
Carcinogenicity (Three-class)Non-required0.7514

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-1.8273LogS
Caco-2 Permeability0.3625LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.3577LD50, mol/kg
Fish Toxicity2.3886pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.3850pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of Exposure
Mechanism of Toxicity
Metabolism
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level
Health Effects
Treatment
Reference
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.[2026685 ]
  2. Capristo E, Mingrone G, De Gaetano A, Addolorato G, Greco AV, Gasbarrini G: A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples. Clin Chim Acta. 1999 Nov;289(1-2):11-21.[10556649 ]
  3. Mingrone G, Tacchino RM, Castagneto M, Finotti E, Greco AV: Use of even-numbered carbon atom dicarboxylic salts in parenteral nutrition as fuel substrate. JPEN J Parenter Enteral Nutr. 1992 Jan-Feb;16(1):32-8.[1738216 ]
  4. Bertuzzi A, Finotti E, Mingrone G, Greco AV: Sebacic acid binding to human plasma albumin. Biochem Pharmacol. 1993 Feb 9;45(3):697-702.[8442769 ]
  5. Curcoy A, Olsen RK, Ribes A, Trenchs V, Vilaseca MA, Campistol J, Osorio JH, Andresen BS, Gregersen N: Late-onset form of beta-electron transfer flavoprotein deficiency. Mol Genet Metab. 2003 Apr;78(4):247-9.[12706375 ]
  6. Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7.[6698061 ]
  7. Fleming AB, Saltzman WM: Pharmacokinetics of the carmustine implant. Clin Pharmacokinet. 2002;41(6):403-19.[12074689 ]
  8. Gregersen N, Kolvraa S, Mortensen PB, Rasmussen K: C6-C10-dicarboxylic aciduria: biochemical considerations in relation to diagnosis of beta-oxidation defects. Scand J Clin Lab Invest Suppl. 1982;161:15-27.[6959231 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassFatty Acyls
SubclassFatty acids and conjugates
Intermediate Tree NodesNot available
Direct ParentMedium-chain fatty acids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsMedium-chain fatty acid - Dicarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

From ClassyFire


Targets

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 ]

From T3DB