ContaminantDB: 3-Oxocholic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:18:07 UTC

Update Date

2016-11-09 01:21:12 UTC

Accession Number

CHEM034882

Identification

Common Name

3-Oxocholic acid

Class

Small Molecule

Description

A 3-oxo steroid that is cholic acid in which the hydroxy group at position 3 has undergone formal oxidation to the corresponding ketone.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxocholan-24-Oic acid	ChEBI
3-Dehydrocholic acid	ChEBI
3-Ketocholic acid	ChEBI
3-Oxocholic acid	ChEBI
7,12-Dihydroxy-3-oxocholanic acid	ChEBI
7alpha,12alpha-Dihydroxy-3-oxo-cholanoic acid	ChEBI
(5b,7a,12a)-7,12-Dihydroxy-3-oxocholan-24-Oate	Generator
(5b,7a,12a)-7,12-Dihydroxy-3-oxocholan-24-Oic acid	Generator
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α,12α)-7,12-dihydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α,12α)-7,12-dihydroxy-3-oxocholan-24-Oic acid	Generator
3-Dehydrocholate	Generator
3-Ketocholate	Generator
3-Oxocholate	Generator
7,12-Dihydroxy-3-oxocholanate	Generator
7a,12a-Dihydroxy-3-oxo-cholanoate	Generator
7a,12a-Dihydroxy-3-oxo-cholanoic acid	Generator
7alpha,12alpha-Dihydroxy-3-oxo-cholanoate	Generator
7Α,12α-dihydroxy-3-oxo-cholanoate	Generator
7Α,12α-dihydroxy-3-oxo-cholanoic acid	Generator
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-Oate	Generator
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-Oic acid	Generator
7alpha,12alpha-Dihydroxy-3-oxo-5beta-cholan-24-Oate	Generator
7Α,12α-dihydroxy-3-oxo-5β-cholan-24-Oate	Generator
7Α,12α-dihydroxy-3-oxo-5β-cholan-24-Oic acid	Generator
7alpha,12alpha-Dihydroxy-3-oxo-5beta-cholan-24-oic acid	HMDB

Chemical Formula

C₂₄H₃₈O₅

Average Molecular Mass

406.556 g/mol

Monoisotopic Mass

406.272 g/mol

CAS Registry Number

2304-89-4

IUPAC Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

SMILES

[H][C@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16+,17+,18+,19-,20-,22+,23+,24-/m1/s1

InChI Key

OEKUSRBIIZNLHZ-ZHDFXGGTSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
3-oxosteroid
12-hydroxysteroid
3-oxo-5-beta-steroid
7-hydroxysteroid
Hydroxysteroid
Oxosteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010190 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.69	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.76 m³·mol⁻¹	ChemAxon
Polarizability	46.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0449000000-a048d1efc6c00034ad57	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2231189000-30c1ecbaf9541625b754	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0009000000-64f2f2abc7d1633027d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0009000000-bcfa1c4097826adbabd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056u-2109000000-fe0a92a5f377efc3a7ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0008900000-dd8b045786455a7b2b5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-1009300000-40bda8fb29d7dc21b644	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-15440129ab1b7eb75b36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0009600000-267c1c0d5a13c4bebc10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-2159000000-97af577c50737e77d152	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9232000000-99073abfe404b118814d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-f0b489debf71eabc30f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0008900000-e453fd1548d30dd5bb33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1029400000-c23a051d71ab55c9d40e	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0062680

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

88108

PubChem Compound ID

5283956

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18583509

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1888771

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26192599

3-Oxocholic acid (CHEM034882)

Structure for CHEM034882: 3-Oxocholic acid