Showing Compound 2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid (FDB021943)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:36 UTC

Update date

2019-11-26 03:21:00 UTC

Primary ID

FDB021943

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid

Description

A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB]

CAS Number

60696-60-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-Oate	HMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oate	hmdb
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-Oic acid	HMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic acid	hmdb
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoate	Generator
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic	HMDB
2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid	hmdb
2b-Hydroxycholate	HMDB
2b-Hydroxycholic acid	HMDB

Showing 1 to 10 of 10 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.41	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.19	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	4	ChemAxon
Refractivity	112.15 m³·mol⁻¹	ChemAxon
Polarizability	48.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C24H40O6

IUPAC name

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

InChI Identifier

InChI=1S/C24H40O6/c1-12(4-7-21(29)30)14-5-6-15-22-16(10-20(28)24(14,15)3)23(2)11-19(27)17(25)8-13(23)9-18(22)26/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13-,14?,15?,16?,17-,18+,19-,20-,22?,23-,24+/m0/s1

InChI Key

IMMADCCLTPCOKH-DLPNMVJGSA-N

Isomeric SMILES

[H][C@@]12C[C@H](O)[C@@H](O)C[C@]1(C)C1C[C@H](O)[C@]3(C)C(CCC3C1[C@H](O)C2)[C@@H](C)CCC(O)=O

Average Molecular Weight

424.5708

Monoisotopic Molecular Weight

424.282489012

Classification

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Subcellular:

Organ and components:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-056u-0349200000-b0b08f5856ad6c87f694	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1100169000-a315711d7850b06d1e6d	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid, TMS_3_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0009700000-4bd7fcfff99cc3ef2be3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0109200000-4e4820960d8c18237874	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l2-2109000000-0e0f6d299d25f4f2ab0f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-0003900000-eb918affd2e4c283a1bd	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1006900000-08a37999c1ecae279d7d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006100000-c42e6ca2acaaf03f9f53	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a70-0007900000-d133c2ed974bbe01feeb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1329200000-37c56b59a2af41ecda9b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9550000000-3ce7e188c553f66bcdeb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-f2b8ea5cd784108b4f12	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-0001900000-087880e8ccd5371d10c3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-022i-1009200000-34b17fc126fb16670448	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

53477680

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00316

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid (FDB021943)

Structure for FDB021943 (2beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid)