Bovine Metabolome Database: Showing metabocard for 3,7-Dihydroxy-12-oxocholanoic acid (BMDB0000400)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:30:02 UTC

Update Date

2020-05-11 20:20:45 UTC

BMDB ID

BMDB0000400

Secondary Accession Numbers

BMDB00400

Metabolite Identification

Common Name

3,7-Dihydroxy-12-oxocholanoic acid

Description

3,7-Dihydroxy-12-oxocholanoic acid, also known as 3α,7α-dihydroxy-12-oxo-5β-cholanate or 12-keto-chenodeoxycholate, 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. 3,7-Dihydroxy-12-oxocholanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oic acid	ChEBI
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanate	ChEBI
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oate	Generator
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oic acid	Generator
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oate	Generator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oate	Generator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oic acid	Generator
3a,7a-Dihydroxy-12-oxo-5b-cholanate	Generator
3a,7a-Dihydroxy-12-oxo-5b-cholanic acid	Generator
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanic acid	Generator
3Α,7α-dihydroxy-12-oxo-5β-cholanate	Generator
3Α,7α-dihydroxy-12-oxo-5β-cholanic acid	Generator
3,7-Dihydroxy-12-oxocholanoate	Generator
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oate	HMDB
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oic acid	HMDB
12-Keto-3a,7a-dihydroxy-5b-cholanate	HMDB
12-Keto-3a,7a-dihydroxy-5b-cholanic acid	HMDB
12-Keto-chenodeoxycholate	HMDB
12-Keto-chenodeoxycholic acid	HMDB
12-Ketochenodeoxycholate	HMDB
12-Ketochenodeoxycholic acid	HMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oate	HMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
12-Oxochenodeoxycholate	HMDB
12-Oxochenodeoxycholic acid	HMDB
3a,7a-Dihydroxy-12-keto-5b-cholanate	HMDB
3a,7a-Dihydroxy-12-keto-5b-cholanic acid	HMDB
3a,7a-Dihydroxy-12-ketocholanate	HMDB
3a,7a-Dihydroxy-12-ketocholanic acid	HMDB
3a,7a-Dihydroxy-12-ketocholate	HMDB
3a,7a-Dihydroxy-12-ketocholic acid	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oate	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oic acid	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoate	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoic acid	HMDB
3a,7a-Dihydroxy-12-oxocholate	HMDB
3a,7a-Dihydroxy-12-oxocholic acid	HMDB
5b-Cholanic acid-3a,7a-diol-12-one	HMDB
12-Monoketocholate	HMDB
12-Monoketocholic acid	HMDB
12-oxo-3,7-Dihydroxycholanoic acid	HMDB
3 alpha, 7 alpha-Dihydroxy-12-one-5 beta-cholanoic acid	HMDB
3 alpha,7 alpha-Dihydroxy-12-keto-5 beta-cholanoic acid	HMDB
3alpha,7alpha-Dihydroxy-12-keto-5beta-cholanoic acid	HMDB
Sodium monoketocholate	HMDB
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
3,7-Dihydroxy-12-oxocholanoic acid	ChEBI

Chemical Formula

C₂₄H₃₈O₅

Average Molecular Weight

406.5555

Monoisotopic Molecular Weight

406.271924326

IUPAC Name

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

12-ketochenodeoxycholic acid

CAS Registry Number

2458-08-4

SMILES

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

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/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1

InChI Key

MIHNUBCEFJLAGN-DMMBONCOSA-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-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
12-oxosteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

oxo-5beta-cholanic acid (CHEBI:16312 )
C24 bile acids, alcohols, and derivatives (LMST04010176 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.56	ALOGPS
logP	3.05	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-0.51	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	109.97 m³·mol⁻¹	ChemAxon
Polarizability	46.44 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-0629000000-3135db41ff8b968182b8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2201198000-bb38056a165602f5feb7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0009100000-bccc650b1cd4508f1aa7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0009000000-c0c7d7baa207e3cc0a05	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056u-1109000000-e710af896d258d339fef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0008900000-dd8b045786455a7b2b5f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-1009300000-40bda8fb29d7dc21b644	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-879f42792050e0f3d07a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0002900000-042ac9446c06cee5ac0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0009700000-eec83a5cd15c56ccdff9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1039100000-e4f72f94d4744ca5a96c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-059i-0009300000-f1bc8868b74d47d136be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-1169100000-6bf02d9105b1f9389f99	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9561000000-ee15985d116087cd50ec	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Gallbladder
Intestine
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Gallbladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000400

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022017

KNApSAcK ID

Not Available

Chemspider ID

85044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5389

PubChem Compound

94235

PDB ID

Not Available

ChEBI ID

16312

References

Synthesis Reference

Fossati Elena; Polentini Fausto; Carrea Giacomo; Riva Sergio Exploitation of the alcohol dehydrogenase-acetone NADP-regeneration system for the enzymatic preparative-scale production of 12-ketochenodeoxycholic acid. Biotechnology and bioengineering (2006), 93(6), 1216-20.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3,7-Dihydroxy-12-oxocholanoic acid (BMDB0000400)

Structure for BMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)