Relevant Data

Food Additives Approved in the United States


General Information

Chemical Names: 3,12-DIHYDROXYCHOLANIC ACID; 3alpha,12alpha-DIHYDROXY-5beta-CHOLAN-24-OIC-ACID
CAS number: 83-44-3
Functional Class: Food Additives
EMULSIFIER

From apps.who.int


Evaluations

Evaluation year: 1973
ADI: 0-1.25 mg/kg bw
Meeting: 17
Specs Code: R
Report: NMRS 53/TRS 539-JECFA 17/36
Tox Monograph: FAS 5/NMRS 53A-JECFA 17/217
Specification: COMPENDIUM ADDENDUM 8/FNP 52 Add.8/203 (METALS LIMITS) (2000); FAO JECFA Monographs 1 vol.1/447

From apps.who.int


Computed Descriptors

Download SDF
2D Structure
CID222528
IUPAC Name(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
InChIInChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
InChI KeyKXGVEGMKQFWNSR-LLQZFEROSA-N
Canonical SMILESCC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
Molecular FormulaC24H40O4
Wikipediadeoxycholate

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight392.58
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity605.0
CACTVS Substructure Key Fingerprint A A A D c f B 4 O A A A A A A A A A A A A A A A A A A A A Y A A A A A w Y M A A A A A A A G D A A A A A G g A A C A A A D x S g g A I C 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 E B I A A A A A Q A A E A A A A A A G I y P C P g A A A A A A A A A D A A A Y A A D A A A Q A A C A A A A A = =
Topological Polar Surface Area77.8
Monoisotopic Mass392.293
Exact Mass392.293
XLogP3None
XLogP3-AA4.9
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count28
Defined Atom Stereocenter Count10
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+0.9288
Human Intestinal AbsorptionHIA+0.9766
Caco-2 PermeabilityCaco2+0.7300
P-glycoprotein SubstrateSubstrate0.6648
P-glycoprotein InhibitorNon-inhibitor0.8737
Inhibitor0.5368
Renal Organic Cation TransporterNon-inhibitor0.8537
Distribution
Subcellular localizationMitochondria0.7746
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7818
CYP450 2D6 SubstrateNon-substrate0.9115
CYP450 3A4 SubstrateSubstrate0.7407
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9456
CYP450 2D6 InhibitorNon-inhibitor0.9781
CYP450 2C19 InhibitorNon-inhibitor0.9707
CYP450 3A4 InhibitorNon-inhibitor0.8405
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9563
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9622
Non-inhibitor0.7246
AMES ToxicityNon AMES toxic0.8794
CarcinogensNon-carcinogens0.9329
Fish ToxicityHigh FHMT0.9848
Tetrahymena Pyriformis ToxicityHigh TPT0.9937
Honey Bee ToxicityHigh HBT0.7800
BiodegradationNot ready biodegradable0.9920
Acute Oral ToxicityIII0.7739
Carcinogenicity (Three-class)Non-required0.7446

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-3.8822LogS
Caco-2 Permeability0.9335LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5624LD50, mol/kg
Fish Toxicity1.0336pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0992pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of Exposure
Mechanism of Toxicity
Metabolism
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)Not listed by IARC.
Minimum Risk Level
Health EffectsChronically high levels of deoxycholic acid are associated with several forms of cancer including colon cancer.
Treatment
Reference
  1. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86.[11316487 ]
  2. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21.[16037564 ]
  3. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56.[12576301 ]
  4. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43.[11907135 ]
  5. Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10.[16548228 ]
  6. Berr F, Stellaard F, Pratschke E, Paumgartner G: Effects of cholecystectomy on the kinetics of primary and secondary bile acids. J Clin Invest. 1989 May;83(5):1541-50.[2708522 ]
  7. Yamaga N, Adachi K, Shimizu K, Miyake S, Sumi F, Miyagawa I, Goto H: Bile acids of patients with renal failure receiving chronic hemodialysis. Steroids. 1986 Nov-Dec;48(5-6):427-38.[3445292 ]
  8. Stellaard F, Paumgartner G, van Berge Henegouwen GP, van der Werf SD: Determination of deoxycholic acid pool size and input rate using [24-13C]deoxycholic acid and serum sampling. J Lipid Res. 1986 Nov;27(11):1222-5.[3559388 ]
  9. Andersen RB, Bruusgaard A: Effect of the common bile acids on the fibrin/fibrinogen fragments in rheumatoid synovial fluid. A possible clue to the ameliorating effect of jaundice in rheumatoid arthritis. Scand J Rheumatol. 1975;4(3):158-64.[52191 ]
  10. Deleze G, Paumgartner G, Karlaganis G, Giger W, Reinhard M, Sidiropoulos D: Bile acid pattern in human amniotic fluid. Eur J Clin Invest. 1978 Feb;8(1):41-5.[417931 ]
  11. Beher WT, Gabbard A, Norum RA, Stradnieks S: Effect of blood high density lipoprotein cholesterol concentration on fecal steroid excretion in humans. Life Sci. 1983 Jun 27;32(26):2933-7.[6865641 ]
  12. Nobuoka A, Takayama T, Miyanishi K, Sato T, Takanashi K, Hayashi T, Kukitsu T, Sato Y, Takahashi M, Okamoto T, Matsunaga T, Kato J, Oda M, Azuma T, Niitsu Y: Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid. Gastroenterology. 2004 Aug;127(2):428-43.[15300575 ]
  13. Rudi J, Schonig T, Stremmel W: -Therapy with ursodeoxycholic acid in primary biliary cirrhosis in pregnancy-. Z Gastroenterol. 1996 Mar;34(3):188-91.[8650973 ]
  14. Heikkinen J, Maentausta O, Tuimala R, Ylostalo P, Janne O: Amniotic fluid bile acids in normal and pathologic pregnancy. Obstet Gynecol. 1980 Jul;56(1):60-4.[7383489 ]
  15. Duret G, Delcour AH: Deoxycholic acid blocks vibrio cholerae OmpT but not OmpU porin. J Biol Chem. 2006 Jul 21;281(29):19899-905. Epub 2006 May 2.[16670088 ]
  16. Costarelli V, Sanders TA: Plasma deoxycholic acid concentration is elevated in postmenopausal women with newly diagnosed breast cancer. Eur J Clin Nutr. 2002 Sep;56(9):925-7.[12209383 ]
  17. Stadler J, Yeung KS, Furrer R, Marcon N, Himal HS, Bruce WR: Proliferative activity of rectal mucosa and soluble fecal bile acids in patients with normal colons and in patients with colonic polyps or cancer. Cancer Lett. 1988 Jan;38(3):315-20.[3349450 ]
  18. Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21.[11344576 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
SubclassBile acids, alcohols and derivatives
Intermediate Tree NodesHydroxy bile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Molecular FrameworkAliphatic homopolycyclic compounds
SubstituentsDihydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - 3-alpha-hydroxysteroid - 12-hydroxysteroid - Hydroxysteroid - Cyclic alcohol - Secondary alcohol - Carboxylic acid - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Alcohol - Aliphatic homopolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

From ClassyFire


Targets

General Function:
G-protein coupled bile acid receptor activity
Specific Function:
Receptor for bile acid. Bile acid-binding induces its internalization, activation of extracellular signal-regulated kinase and intracellular cAMP production. May be involved in the suppression of macrophage functions by bile acids.
Gene Name:
GPBAR1
Uniprot ID:
Q8TDU6
Molecular Weight:
35247.795 Da
References
  1. Yoneno K, Hisamatsu T, Shimamura K, Kamada N, Ichikawa R, Kitazume MT, Mori M, Uo M, Namikawa Y, Matsuoka K, Sato T, Koganei K, Sugita A, Kanai T, Hibi T: TGR5 signalling inhibits the production of pro-inflammatory cytokines by in vitro differentiated inflammatory and intestinal macrophages in Crohn's disease. Immunology. 2013 May;139(1):19-29. doi: 10.1111/imm.12045. [23566200 ]
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
Gene Name:
NR1H4
Uniprot ID:
Q96RI1
Molecular Weight:
55913.915 Da
References
  1. Fujino T, Une M, Imanaka T, Inoue K, Nishimaki-Mogami T: Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. J Lipid Res. 2004 Jan;45(1):132-8. Epub 2003 Sep 16. [13130122 ]
General Function:
S-nitrosoglutathione binding
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:
GSTP1
Uniprot ID:
P09211
Molecular Weight:
23355.625 Da
References
  1. Nobuoka A, Takayama T, Miyanishi K, Sato T, Takanashi K, Hayashi T, Kukitsu T, Sato Y, Takahashi M, Okamoto T, Matsunaga T, Kato J, Oda M, Azuma T, Niitsu Y: Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid. Gastroenterology. 2004 Aug;127(2):428-43. [15300575 ]
General Function:
Steroid delta-isomerase activity
Gene Name:
ksi
Uniprot ID:
P07445
Molecular Weight:
14535.48 Da
General Function:
Metal ion binding
Gene Name:
ppcA
Uniprot ID:
Q8GGK7
Molecular Weight:
9747.54 Da
General Function:
Ribosome binding
Specific Function:
Involved in the biogenesis of the 60S ribosomal subunit and translational activation of ribosomes. Together with SBDS, triggers the GTP-dependent release of EIF6 from 60S pre-ribosomes in the cytoplasm, thereby activating ribosomes for translation competence by allowing 80S ribosome assembly and facilitating EIF6 recycling to the nucleus, where it is required for 60S rRNA processing and nuclear export. Has low intrinsic GTPase activity. GTPase activity is increased by contact with 60S ribosome subunits.
Gene Name:
EFTUD1
Uniprot ID:
Q7Z2Z2
Molecular Weight:
125428.745 Da
General Function:
Choloylglycine hydrolase activity
Specific Function:
The enzyme catalyzes the degradation of conjugated bile acids in the mammalian gut.
Gene Name:
cbh
Uniprot ID:
P54965
Molecular Weight:
37185.0 Da
General Function:
Succinate-semialdehyde dehydrogenase [nad(p)+] activity
Specific Function:
Acts on lactaldehyde as well as other aldehydes.
Gene Name:
aldA
Uniprot ID:
P25553
Molecular Weight:
52272.37 Da
General Function:
Identical protein binding
Specific Function:
AcrA-AcrB-AcrZ-TolC is a drug efflux protein complex with broad substrate specificity that uses the proton motive force to export substrates.Involved in contact-dependent growth inhibition (CDI), acts downstream of BamA, the receptor for CDI. Its role in CDI is independent of the AcrA-AcrB-TolC efflux pump complex.
Gene Name:
acrB
Uniprot ID:
P31224
Molecular Weight:
113572.75 Da
General Function:
Iron ion binding
Specific Function:
Cytochrome c oxidase is the component of the respiratory chain that catalyzes the reduction of oxygen to water. Subunits 1-3 form the functional core of the enzyme complex. Co I is the catalytic subunit of the enzyme. Electrons originating in cytochrome c are transferred via the copper A center of subunit 2 and heme a of subunit 1 to the bimetallic center formed by heme a3 and copper B. This cytochrome c oxidase shows proton pump activity across the membrane in addition to the electron transfer.
Gene Name:
ctaD
Uniprot ID:
P33517
Molecular Weight:
63146.395 Da
General Function:
Cytochrome-c oxidase activity
Specific Function:
Subunits I and II form the functional core of the enzyme complex. Electrons originating in cytochrome c are transferred via heme a and Cu(A) to the binuclear center formed by heme a3 and Cu(B).
Gene Name:
ctaC
Uniprot ID:
Q03736
Molecular Weight:
32930.42 Da

From T3DB