Bovine Metabolome Database: Showing metabocard for Allocholic acid (BMDB0000505)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:48 UTC

Update Date

2020-05-11 20:21:01 UTC

BMDB ID

BMDB0000505

Secondary Accession Numbers

BMDB00505

Metabolite Identification

Common Name

Allocholic acid

Description

Allocholic acid, also known as allocholate or 5alpha-cholate, 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. Based on a literature review a significant number of articles have been published on Allocholic acid.

Structure

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

Synonyms

Value	Source
3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoic acid	ChEBI
5alpha-Cholic acid	ChEBI
Allocholate	Kegg
(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5alpha,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-Oate	Generator
(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid	Generator
3a,7a,12a-Trihydroxy-5a-cholanoate	Generator
3a,7a,12a-Trihydroxy-5a-cholanoic acid	Generator
3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoate	Generator
5a-Cholate	Generator
5a-Cholic acid	Generator
5alpha-Cholate	Generator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid	HMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate	HMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid	HMDB
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate	HMDB
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate	HMDB
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oate	HMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oic acid	HMDB
3a,7a,12a-Trihydroxycholanate	HMDB
3a,7a,12a-Trihydroxycholanic acid	HMDB
5alpha-Allocholic acid	HMDB
5Α-allocholic acid	HMDB
Allocholic acid	HMDB

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.579

Monoisotopic Molecular Weight

408.287574388

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

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-PGHAKIONSA-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
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:81308 )
C24 bile acids, alcohols, and derivatives (C17737 )
C24 bile acids, alcohols, and derivatives (LMST04010092 )

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	47.2 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	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_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 (TMS_4_1) - 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 - 10V, Positive	splash10-00di-0009000000-1fb995e2a2a10479ff54	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0009000000-814238696e6fb3e11648	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0bta-1983000000-7ec50e0786625a29b904	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0001900000-a764d2a5e3d1918ae5fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0007900000-d1ed92b278bc96ae6ebd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1019600000-c907470476ed433e714e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0abc-0019500000-627bd12690a4dc559a07	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-4379100000-2566436d8a667838d682	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-8930000000-8acc72953d3f45da3f73	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

HMDB0000505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5491

PubChem Compound

160636

PDB ID

Not Available

ChEBI ID

81308

References

Synthesis Reference

Mitra, Manindra N.; Elliott, William Hueckel. Bile acids. XXIII. New direct synthesis of allocholic acid and its 3b isomer. Journal of Organic Chemistry (1968), 33(1), 175-81.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Allocholic acid (BMDB0000505)

Structure for BMDB0000505 (Allocholic acid)