Bovine Metabolome Database: Showing metabocard for 7-Ketodeoxycholic acid (BMDB0000391)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:29:52 UTC

Update Date

2020-05-11 20:20:42 UTC

BMDB ID

BMDB0000391

Secondary Accession Numbers

BMDB00391

Metabolite Identification

Common Name

7-Ketodeoxycholic acid

Description

7-Ketodeoxycholic acid, also known as 7-oxodeoxycholate, 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. 7-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
(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-Oic acid	ChEBI
3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoic acid	ChEBI
3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanate	ChEBI
3alpha,12alpha-Diol-7-one-5beta-cholanoic acid	ChEBI
7-Oxodeoxycholic acid	ChEBI
(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-Oate	Generator
(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-Oic acid	Generator
(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oic acid	Generator
3a,12a-Dihydroxy-7-keto-5b-cholanoate	Generator
3a,12a-Dihydroxy-7-keto-5b-cholanoic acid	Generator
3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoate	Generator
3Α,12α-dihydroxy-7-keto-5β-cholanoate	Generator
3Α,12α-dihydroxy-7-keto-5β-cholanoic acid	Generator
3a,12a-Dihydroxy-7-oxo-5b-cholanate	Generator
3a,12a-Dihydroxy-7-oxo-5b-cholanic acid	Generator
3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanic acid	Generator
3Α,12α-dihydroxy-7-oxo-5β-cholanate	Generator
3Α,12α-dihydroxy-7-oxo-5β-cholanic acid	Generator
3a,12a-Diol-7-one-5b-cholanoate	Generator
3a,12a-Diol-7-one-5b-cholanoic acid	Generator
3alpha,12alpha-Diol-7-one-5beta-cholanoate	Generator
3Α,12α-diol-7-one-5β-cholanoate	Generator
3Α,12α-diol-7-one-5β-cholanoic acid	Generator
7-Oxodeoxycholate	Generator
7-Ketodeoxycholate	Generator
(3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-Oate	HMDB
(3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-Oic acid	HMDB
3 alpha,12 alpha-Diol-7-one-5 beta-cholanoate	HMDB
3 alpha,12 alpha-Diol-7-one-5 beta-cholanoic acid	HMDB
3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoate	HMDB
3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoic acid	HMDB
3a,12a-Dihydroxy-7-oxo-5b-cholan-24-Oate	HMDB
3a,12a-Dihydroxy-7-oxo-5b-cholan-24-Oic acid	HMDB
7-Ketodeoxycholic acid, (3alpha,12alpha)-isomer	HMDB
(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-Dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
7-Ketodeoxycholic acid	ChEBI

Chemical Formula

C₂₄H₃₈O₅

Average Molecular Weight

406.5555

Monoisotopic Molecular Weight

406.271924326

IUPAC Name

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

Traditional Name

7-ketodeoxycholic acid

CAS Registry Number

911-40-0

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])C(=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/h13-18,20,22,25,27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,20+,22+,23+,24-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

7-oxo steroid (CHEBI:16390 )
oxo-5beta-cholanic acid (CHEBI:16390 )
C24 bile acids, alcohols, and derivatives (LMST04010184 )

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	2.61	ALOGPS
logP	2.87	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-0.33	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	109.86 m³·mol⁻¹	ChemAxon
Polarizability	46.22 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	splash10-03di-0229000000-f4573054b1373ba25c43	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-1200097000-a328d301b9f2734f7a3f	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 (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_1_5) - 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_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 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 (TMS_3_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 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
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0009300000-ca7ded990dc45187bf33	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0019000000-8ae130c589121cdfb070	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-2793000000-011c0c178df6b144dfe2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-2793000000-e7a868da91e004e56a7b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0009100000-e53168576c29dec4ba1b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00du-0009000000-f85ab4860a22a24d931d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056v-0109000000-fa17bdbd4a2e5abdc658	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0008900000-88fb88b08cd50a69ab8d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-1009300000-b632dccfee47dc4f5e6c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9207000000-316b16e5098a68abb1d2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0002900000-074c6bb08c4c08acb7c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0009700000-3e7500c867ff6bbdf776	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0039000000-2dcd29515d1454079783	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-059i-0009400000-1677f5d16dbb699fffc4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-1179100000-2e7695e0d4a36f0d2b25	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9461000000-5853807a64c3c0ca1121	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
Kidney
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
Kidney	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

HMDB0000391

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022009

KNApSAcK ID

Not Available

Chemspider ID

163659

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5380

PubChem Compound

188292

PDB ID

Not Available

ChEBI ID

16390

References

Synthesis Reference

Bortolini, Olga; Cova, Umberto; Fantin, Giancarlo; Medici, Alessandro. A new non-enzymic route to chenodeoxycholic acid. Chemistry Letters (1996), (5), 335-336

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 7-Ketodeoxycholic acid (BMDB0000391)

Structure for BMDB0000391 (7-Ketodeoxycholic acid)