Bovine Metabolome Database: Showing metabocard for Isolithocholic acid (BMDB0000717)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:25 UTC

Update Date

2020-05-11 20:09:08 UTC

BMDB ID

BMDB0000717

Secondary Accession Numbers

BMDB00717

Metabolite Identification

Common Name

Isolithocholic acid

Description

Isolithocholic acid, also known as 3-epilithocholate or beta-lithocholanate, 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. Based on a literature review a significant number of articles have been published on Isolithocholic acid.

Structure

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

Synonyms

Value	Source
(3beta,5beta)-3-Hydroxycholan-24-Oic acid	ChEBI
3-Epilithocholic acid	ChEBI
3beta-Hydroxy-5beta-cholan-24-Oic acid	ChEBI
3beta-Lithocholic acid	ChEBI
beta-Lithocholanic acid	ChEBI
beta-Lithocholic acid	ChEBI
(3b,5b)-3-Hydroxycholan-24-Oate	Generator
(3b,5b)-3-Hydroxycholan-24-Oic acid	Generator
(3beta,5beta)-3-Hydroxycholan-24-Oate	Generator
(3Β,5β)-3-hydroxycholan-24-Oate	Generator
(3Β,5β)-3-hydroxycholan-24-Oic acid	Generator
3-Epilithocholate	Generator
3b-Hydroxy-5b-cholan-24-Oate	Generator
3b-Hydroxy-5b-cholan-24-Oic acid	Generator
3beta-Hydroxy-5beta-cholan-24-Oate	Generator
3Β-hydroxy-5β-cholan-24-Oate	Generator
3Β-hydroxy-5β-cholan-24-Oic acid	Generator
3b-Lithocholate	Generator
3b-Lithocholic acid	Generator
3beta-Lithocholate	Generator
3Β-lithocholate	Generator
3Β-lithocholic acid	Generator
b-Lithocholanate	Generator
b-Lithocholanic acid	Generator
beta-Lithocholanate	Generator
Β-lithocholanate	Generator
Β-lithocholanic acid	Generator
b-Lithocholate	Generator
b-Lithocholic acid	Generator
beta-Lithocholate	Generator
Β-lithocholate	Generator
Β-lithocholic acid	Generator
Isolithocholate	Generator
3b-Hydroxy-5b-cholanate	HMDB
3b-Hydroxy-5b-cholanic acid	HMDB
3b-Hydroxy-5b-cholanoate	HMDB
3b-Hydroxy-5b-cholanoic acid	HMDB
5b-Cholanic acid-3b-ol	HMDB
Acid, isolithocholic	HMDB
Acid, lithocholic	HMDB
Lithocholate	HMDB
Lithocholic acid	HMDB

Chemical Formula

C₂₄H₄₀O₃

Average Molecular Weight

376.5726

Monoisotopic Molecular Weight

376.297745146

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1534-35-6

SMILES

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

InChI Identifier

InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/m1/s1

InChI Key

SMEROWZSTRWXGI-WFVDQZAMSA-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-beta-hydroxysteroid
Cyclic alcohol
Secondary alcohol
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

bile acid (CHEBI:81253 )
C24 bile acids, alcohols, and derivatives (LMST04010004 )

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	4.38	ALOGPS
logP	5.02	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.68 m³·mol⁻¹	ChemAxon
Polarizability	45.89 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	splash10-0hft-0109000000-d80c67969566eb069712	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-3214890000-a148637510771fd69f57	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 (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_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0129000000-066ac41ad9941f9e21f4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0249000000-cce770467236fef9c102	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001m-9610000000-9bf43cf0de56ef3b9157	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0249000000-319218499f72e4ee3f1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0009000000-f631439c42560b6112dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bu3-0029000000-77d9dd354e5acfcbb059	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1195000000-4e93d1691883a980ad09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-bc8a31ce5625ab01cbf9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-1009000000-703fb777c311a25b0d15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-6c71a6df88d4f84121d0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-eccc9e9b8c78169f5313	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0009000000-7777c272612ec6c534f1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05di-3019000000-e5596a2bcefec4be517a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0009000000-4fc9c94a2a74d03b596d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-6579000000-8d70683d9c59bbc7c41e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-8970000000-50834929c8da38b179bf	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Gallbladder
Intestine

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

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000717

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022201

KNApSAcK ID

Not Available

Chemspider ID

144522

KEGG Compound ID

C17658

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5685

PubChem Compound

164853

PDB ID

Not Available

ChEBI ID

81253

References

Synthesis Reference

Radominska-Pyrek, Anna; Huynh, Triet; Lester, Roger; St. Pyrek, Jan. Preparation and characterization of 3-monohydroxylated bile acids of different side chain length and configuration at C-3. Novel approach to the synthesis of 24-norlithocholic acid. Journal of Lipid Research (1986), 27(1), 102-13.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Isolithocholic acid (BMDB0000717)

Structure for BMDB0000717 (Isolithocholic acid)