DESOXYCHOLIC ACID
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 SDF2D Structure | |
CID | 222528 |
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 |
InChI | InChI=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 Key | KXGVEGMKQFWNSR-LLQZFEROSA-N |
Canonical SMILES | CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C |
Molecular Formula | C24H40O4 |
Wikipedia | deoxycholate |
From Pubchem
Computed Properties
Property Name | Property Value |
---|---|
Molecular Weight | 392.58 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 4 |
Complexity | 605.0 |
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 Area | 77.8 |
Monoisotopic Mass | 392.293 |
Exact Mass | 392.293 |
XLogP3 | None |
XLogP3-AA | 4.9 |
Compound Is Canonicalized | True |
Formal Charge | 0 |
Heavy Atom Count | 28 |
Defined Atom Stereocenter Count | 10 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9288 |
Human Intestinal Absorption | HIA+ | 0.9766 |
Caco-2 Permeability | Caco2+ | 0.7300 |
P-glycoprotein Substrate | Substrate | 0.6648 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.8737 |
Inhibitor | 0.5368 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8537 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7746 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7818 |
CYP450 2D6 Substrate | Non-substrate | 0.9115 |
CYP450 3A4 Substrate | Substrate | 0.7407 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9456 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9781 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9707 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8405 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9563 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9622 |
Non-inhibitor | 0.7246 | |
AMES Toxicity | Non AMES toxic | 0.8794 |
Carcinogens | Non-carcinogens | 0.9329 |
Fish Toxicity | High FHMT | 0.9848 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9937 |
Honey Bee Toxicity | High HBT | 0.7800 |
Biodegradation | Not ready biodegradable | 0.9920 |
Acute Oral Toxicity | III | 0.7739 |
Carcinogenicity (Three-class) | Non-required | 0.7446 |
From admetSAR
ADMET Predicted Profile --- Regression
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.8822 | LogS |
Caco-2 Permeability | 0.9335 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.5624 | LD50, mol/kg |
Fish Toxicity | 1.0336 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 1.0992 | pIGC50, 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 Effects | Chronically high levels of deoxycholic acid are associated with several forms of cancer including colon cancer. |
Treatment | |
Reference |
|
From T3DB
Taxonomic Classification
Kingdom | Organic compounds |
---|---|
Superclass | Lipids and lipid-like molecules |
Class | Steroids and steroid derivatives |
Subclass | Bile acids, alcohols and derivatives |
Intermediate Tree Nodes | Hydroxy bile acids, alcohols and derivatives |
Direct Parent | Dihydroxy bile acids, alcohols and derivatives |
Alternative Parents | |
Molecular Framework | Aliphatic homopolycyclic compounds |
Substituents | Dihydroxy 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 |
Description | This 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
- 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
- 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
- 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