Bovine Metabolome Database: Showing metabocard for 12-Ketodeoxycholic acid (BMDB0000328)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:28:41 UTC

Update Date

2020-04-22 15:02:58 UTC

BMDB ID

BMDB0000328

Secondary Accession Numbers

BMDB00328

Metabolite Identification

Common Name

12-Ketodeoxycholic acid

Description

12-Ketodeoxycholic acid, also known as 12-dehydrodeoxycholate or 12-ketolithocholate, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 12-Ketodeoxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
12-Ketodeoxycholate	Generator
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
12-Dehydrodeoxycholate	HMDB
12-Dehydrodeoxycholic acid	HMDB
12-Ketolithocholate	HMDB
12-Ketolithocholic acid	HMDB
12-oxo-3a-Hydroxy-5b-cholanate	HMDB
12-oxo-3a-Hydroxy-5b-cholanic acid	HMDB
12-Oxolithocholate	HMDB
12-Oxolithocholic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oate	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanate	HMDB
3a-Hydroxy-12-oxo-5b-cholanic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanoate	HMDB
3a-Hydroxy-12-oxo-5b-cholanoic acid	HMDB
3-Hydroxy-12-ketocholanoic acid	HMDB
12-Ketolithocholic acid, (3beta,5beta)-isomer	HMDB
3 alpha-Hydroxy-12-keto-5 beta-cholanoic acid	HMDB
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-Hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₃₈O₄

Average Molecular Weight

390.5561

Monoisotopic Molecular Weight

390.277009704

IUPAC Name

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

Traditional Name

12-ketolithocholic acid

CAS Registry Number

5130-29-0

SMILES

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

InChI Identifier

InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

InChI Key

CVNYHSDFZXHMMJ-VPUMZWJWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
12-oxosteroid
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

C24 bile acids, alcohols, and derivatives (LMST04010155 )

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	3.78	ALOGPS
logP	4.35	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.37 m³·mol⁻¹	ChemAxon
Polarizability	45.52 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	splash10-02wa-0309000000-107696c445ee2097f3ad	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-2200690000-116b9b25c9a86c4f4259	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_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 (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_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
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-0973000000-c05ff42fd008465bafb3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0009000000-5dee4fb39c808ac6bd6b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0009000000-a3abedb65cc015b126a4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-0973000000-27eab1754ab850b5d833	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-8cbf377d4ac0ead7f478	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05i0-0009000000-f445f21e6bb19a3e03e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0400-3519000000-e95ed419ca30aa610aad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-d2798e61ab8bdbb8b70c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-1009000000-08abf1a9cb419252bf5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-1e75d302e82f8e8c004f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0596-0009000000-e1273a9cf6cd8fec5090	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-2295000000-496364ed24778803b66a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9620000000-568df3571bdbbb289061	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-0312986dad14766b7b5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-0009000000-9c3b566629f1b019e8c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1079000000-22dd9a5f612d7b635280	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000328

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021953

KNApSAcK ID

Not Available

Chemspider ID

2338365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5317

PubChem Compound

3080612

PDB ID

Not Available

ChEBI ID

803536

References

Synthesis Reference

Suzuki, Yoshinori; Okamura, Akio; Shimomura, Kazuo; Suzuki, Tadayuki. Purification of bile acids. Jpn. Kokai Tokkyo Koho (1985), 6 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 12-Ketodeoxycholic acid (BMDB0000328)

Structure for BMDB0000328 (12-Ketodeoxycholic acid)