Bovine Metabolome Database: Showing metabocard for Ursocholic acid (BMDB0000917)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:35 UTC

Update Date

2020-05-11 20:21:48 UTC

BMDB ID

BMDB0000917

Secondary Accession Numbers

BMDB00917

Metabolite Identification

Common Name

Ursocholic acid

Description

Ursocholic acid, also known as 7-epicholic acid or 7-epicholate, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Ursocholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid	ChEBI
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oic acid	ChEBI
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acid	ChEBI
7-Epicholic acid	ChEBI
7beta-Hydroxyisocholic acid	Kegg
(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oate	Generator
(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oic acid	Generator
3a,7b,12a-Trihydroxy-5b-cholan-24-Oate	Generator
3a,7b,12a-Trihydroxy-5b-cholan-24-Oic acid	Generator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oate	Generator
3Α,7β,12α-trihydroxy-5β-cholan-24-Oate	Generator
3Α,7β,12α-trihydroxy-5β-cholan-24-Oic acid	Generator
3a,7b,12a-Trihydroxy-5b-cholanate	Generator
3a,7b,12a-Trihydroxy-5b-cholanic acid	Generator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanate	Generator
3Α,7β,12α-trihydroxy-5β-cholanate	Generator
3Α,7β,12α-trihydroxy-5β-cholanic acid	Generator
7-Epicholate	Generator
7b-Hydroxyisocholate	Generator
7b-Hydroxyisocholic acid	Generator
7beta-Hydroxyisocholate	Generator
7Β-hydroxyisocholate	Generator
7Β-hydroxyisocholic acid	Generator
Ursocholate	Generator
3a,7b,12a-Trihydroxy-5b-cholanoate	HMDB
3a,7b,12a-Trihydroxy-5b-cholanoic acid	HMDB
3a,7b,12a-Trihydroxycholanate	HMDB
3a,7b,12a-Trihydroxycholanic acid	HMDB
3 alpha,7 beta,12 alpha-Trihydroxy-5 beta-cholan-24-Oic acid	HMDB

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

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

Traditional Name

ursocholic acid

CAS Registry Number

2955-27-3

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@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C24H40O5/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/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1

InChI Key

BHQCQFFYRZLCQQ-UTLSPDKDSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:81240 )
C24 bile acids, alcohols, and derivatives (LMST04010088 )

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	2.26	ALOGPS
logP	2.48	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.79 m³·mol⁻¹	ChemAxon
Polarizability	47.04 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	splash10-03ec-0439000000-abd2a5c162e23ea0d78f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1100049000-ae391322cbbc458fdb46	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_1) - 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
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1019800000-4a5ffc11cb3fa93e46cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-7f097ee7b44073c18648	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-07966770f57ff86aa177	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0009100000-915584a506714c470270	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0009000000-f970a088fc3d9cdb8fe6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-017j-3109000000-bb054743c390ef266044	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0008900000-ed202aebd950e99a7852	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-1009300000-db2a4b9107b891a8ef3a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9006000000-87df039839010127a1a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0001900000-450d1e4d25aae2ed99f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0005900000-630ea179fce67da6f208	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0r09-0019200000-0754019de78fe2be314d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0abc-0009400000-fe4f5c75dd7ef6e8d9ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-059l-3159100000-f0eff49c7e8da5d00c58	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9640000000-28284141ad8f72ab8fe1	View in MoNA

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

HMDB0000917

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022316

KNApSAcK ID

Not Available

Chemspider ID

109088

KEGG Compound ID

C17644

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5871

PubChem Compound

122340

PDB ID

Not Available

ChEBI ID

81240

References

Synthesis Reference

Terada, Masaki; Sato, Manabu; Horie, Yoshiaki; Takatsu, Mitsumune; Minami, Junichi. Production of ursocholic acid. Jpn. Kokai Tokkyo Koho (1986), 9 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Ursocholic acid (BMDB0000917)

Structure for BMDB0000917 (Ursocholic acid)