Showing Compound 1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid (FDB021952)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:44 UTC

Update date

2015-07-21 06:56:54 UTC

Primary ID

FDB021952

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid

Description

1b,3a,12a-Trihydroxy-5b-cholanoic acid is 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. [HMDB]

CAS Number

80434-32-8

Structure

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

Synonyms

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Synonym	Source
(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	Generator, HMDB
1,3,12-Trihydroxy-(5b)-cholan-24-Oate	HMDB
1,3,12-Trihydroxy-(5b)-cholan-24-oate	hmdb
1,3,12-Trihydroxy-(5b)-cholan-24-Oic acid	HMDB
1,3,12-Trihydroxy-(5b)-cholan-24-oic acid	hmdb
1b,3a,12a-Trihydroxy-5b-cholan-24-Oate	HMDB
1b,3a,12a-Trihydroxy-5b-cholan-24-oate	hmdb
1b,3a,12a-Trihydroxy-5b-cholan-24-Oic acid	HMDB
1b,3a,12a-Trihydroxy-5b-cholan-24-oic acid	hmdb
1b,3a,12a-Trihydroxy-5b-cholanoate	Generator

Showing 1 to 10 of 11 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	2.46	ALOGPS
logP	2.49	ChemAxon
logS	-3.7	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	110.67 m³·mol⁻¹	ChemAxon
Polarizability	47.46 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

C24H40O5

IUPAC name

(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

InChI Identifier

InChI=1S/C24H40O5/c1-13(4-9-22(28)29)17-7-8-18-16-6-5-14-10-15(25)11-20(26)23(14,2)19(16)12-21(27)24(17,18)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

DAKYVYUAVGJDRK-LFMRMFNLSA-N

Isomeric SMILES

C[C@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)C[C@@H](O)[C@]4(C)C3C[C@H](O)[C@]12C

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

Classification

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
1-hydroxysteroid
12-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

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Primary biliary cirrhosis

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Organ and components:

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	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-0229000000-eeb650163ff13c21bde8	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-1010049000-b3e7856d53a8de4e67bf	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid, TBDMS_2_4, 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	splash10-00dl-0009100000-e38101baf95cd1f6df66	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0009000000-d2d86b868da22fab2c66	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-3139000000-583fe7951b76313ec5c3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0008900000-c90a6fd35d955faa9feb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-1009300000-b79cfceb35f5907afb70	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9007000000-1f85b1506bbd76dd1242	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-ec1d9319a9eaf1f2aba6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0001900000-68e3200734e1d0985f37	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1009400000-d4c82ad5f07330ebfe9f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0abc-0029700000-df0c3f0d9008673f328b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-059i-3249200000-96d3a93ff398db4a71ea	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05q9-6950000000-c30ac6ba5ad031ba5e07	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

53477683

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00326

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

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid (FDB021952)

Structure for FDB021952 (1beta,3alpha,12alpha-Trihydroxy-5beta-cholanoic acid)