Bovine Metabolome Database: Showing metabocard for 6a,12a-Dihydroxylithocholic acid (BMDB0000527)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:32:13 UTC

Update Date

2020-05-11 20:21:05 UTC

BMDB ID

BMDB0000527

Secondary Accession Numbers

BMDB00527

Metabolite Identification

Common Name

6a,12a-Dihydroxylithocholic acid

Description

6a,12a-Dihydroxylithocholic acid, also known as 3a,6a,12a-trihydroxy-5b-cholan-24-Oate, 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 6a,12a-Dihydroxylithocholic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6a,12a-Dihydroxylithocholate	Generator
3a,6a,12a-Trihydroxy-5b-cholan-24-Oate	HMDB
3a,6a,12a-Trihydroxy-5b-cholan-24-Oic acid	HMDB
3a,6a,12a-Trihydroxycholate	HMDB
3a,6a,12a-Trihydroxycholic acid	HMDB
(4R)-4-[(1S,2R,5R,8S,10R,11S,14R,15R,16S)-5,8,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
6a,12a-Dihydroxylithocholic acid	Generator

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

(4R)-4-[(1S,2R,5R,8S,10R,11S,14R,15R,16S)-5,8,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

3a,6a,12a-trihydroxycholate

CAS Registry Number

21066-18-2

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[C@H](O)C2C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C24H40O5/c1-13(4-7-22(28)29)16-5-6-17-15-11-20(26)19-10-14(25)8-9-23(19,2)18(15)12-21(27)24(16,17)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19?,20+,21+,23-,24-/m1/s1

InChI Key

GCAHOAMXTYBLNZ-YAZNBHORSA-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
3-alpha-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	1.97	ALOGPS
logP	2.48	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-0.4	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	47.38 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	splash10-01ox-0329000000-4b46ad1b2dacce1bf218	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1100039000-760033c57e267918f963	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0009000000-f5b70cbc59d5ea066854	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0009000000-a1598b92858405ff74e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0931-2109000000-5040f3ce8f75f7259313	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-0009700000-8dc05bd9542a54f1f91b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-0009200000-9a24af3f58b590ac86cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9007000000-acd067cd1da85248dd66	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-ec1d9319a9eaf1f2aba6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0007900000-ee1a89f01c0c399bba19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ly9-1019100000-1ab1ccc5b19c01372e0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0abc-0009400000-c7e4fe766731000e676e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-059l-3249100000-f20fd02a8db7144f53cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9630000000-8f0dedbb78fb6914fa90	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

HMDB0000527

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022095

KNApSAcK ID

Not Available

Chemspider ID

17215966

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5512

PubChem Compound

22833529

PDB ID

Not Available

ChEBI ID

175285

References

Synthesis Reference

Iida, Takashi; Tamaru, Tamaaki; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. XVIII. Synthesis of stereoisomeric 3,6,12a-trihydroxy-5b-cholanoic acids. Journal of Lipid Research (1991), 32(4), 649-58.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 6a,12a-Dihydroxylithocholic acid (BMDB0000527)

Structure for BMDB0000527 (6a,12a-Dihydroxylithocholic acid)