Bovine Metabolome Database: Showing metabocard for 3a,7a,12a,19-Tetrahydroxy-5b-cholanoic acid (BMDB0000340)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:28:55 UTC

Update Date

2020-05-11 20:08:17 UTC

BMDB ID

BMDB0000340

Secondary Accession Numbers

BMDB00340

Metabolite Identification

Common Name

3a,7a,12a,19-Tetrahydroxy-5b-cholanoic acid

Description

3a,7a,12a,19-Tetrahydroxy-5b-cholanoic acid, also known as 3,7,12,19-thca, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Based on a literature review a significant number of articles have been published on 3a,7a,12a,19-Tetrahydroxy-5b-cholanoic acid.

Structure

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

Synonyms

Value	Source
3a,7a,12a,19-Tetrahydroxy-5b-cholanoate	Generator
3,7,12,19-THCA	MeSH
3,7,12,19-Tetrahydroxycholanoic acid	MeSH
3a,7a,12a,19-Tetrahydroxy-5b-cholan-24-Oate	HMDB
3a,7a,12a,19-Tetrahydroxy-5b-cholan-24-Oic acid	HMDB
(4R)-4-[(1S,2R,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator, HMDB
3alpha,7alpha,12alpha,19-Tetrahydroxy-5beta-cholan-24-Oic acid	MeSH, HMDB

Chemical Formula

C₂₄H₄₀O₆

Average Molecular Weight

424.5708

Monoisotopic Molecular Weight

424.282489012

IUPAC Name

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

Traditional Name

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

CAS Registry Number

171524-64-4

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@]12CO

InChI Identifier

InChI=1S/C24H40O6/c1-13(3-6-21(29)30)16-4-5-17-22-18(11-20(28)23(16,17)2)24(12-25)8-7-15(26)9-14(24)10-19(22)27/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23-,24-/m1/s1

InChI Key

RFSKRKUKTCLIAV-OWXKUJNZSA-N

Chemical Taxonomy

Description

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

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010126 )

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	1.22	ALOGPS
logP	1.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.093	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	112.56 m³·mol⁻¹	ChemAxon
Polarizability	47.91 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	splash10-0bu3-0569200000-c724deddea0794c171b6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-004i-2100159000-6e1fcf87c606060d30cc	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_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_2_10) - 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 (TMS_3_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0009600000-70600db74b6acb61211c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0009100000-49c2cffe03e2e60f22fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002k-1109000000-ccd4aca8f0bff807a8e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-0003900000-8adfc90518b7a32e1a65	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-1009700000-30bd509011b013a0bb85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-7009000000-3b2d081017bbf7ce399a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0570-0008900000-1257dece5f78104794f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0550-1009100000-69f08f15b2ecae209b5e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9770000000-c6a1204ae4e44ba4c905	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-fd0b098a165473974103	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0002900000-522cde860acb86cd80f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004m-0019100000-49bd77c03794201e6eaa	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

HMDB0000340

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021964

KNApSAcK ID

Not Available

Chemspider ID

4446993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5329

PubChem Compound

5283905

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Kurosawa, Takao; Nomura, Yukihiro; Mahara, Reijiro; Yoshimura, Teruki; Kimura, Akihiko; Ikegawa, Shigeo; Tohma, Masahiko. Synthesis of 19-hydroxylated bile acids and identification of 3a,7a,12a,19-tetrahydroxy-5b-cholan-24-oic acid in human neonatal urine. Chem Pharm Bull (Tokyo). 1995 Sep;43(9):1551-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3a,7a,12a,19-Tetrahydroxy-5b-cholanoic acid (BMDB0000340)

Structure for BMDB0000340 (3a,7a,12a,19-Tetrahydroxy-5b-cholanoic acid)