ChemFOnt: Showing chemical card for 5b-Cholestane-3a,7a,12a,24,25-pentol (CFc000000432)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:49 UTC

Chemfont ID

CFc000000432

Molecule Identification

Common Name

5b-Cholestane-3a,7a,12a,24,25-pentol

Definition

5b-Cholestane-3a,7a,12a,24,25-pentol has been found excreted in the urine from a patient with sitosterolemia as glycine- and taurine-conjugated bile acids (PMID 7896564 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3a,7a,12a,24,25-Pentahydroxycoprostane	HMDB
3alpha,7alpha,12alpha,24R,25-Pentahydroxy-5beta-cholestane	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,24R,25-pentol	HMDB
5b-Cholestane-3a,7a,12a,24R,25-pentol	HMDB
5Β-cholestane-3α,7α,12α,24R,25-pentol	HMDB

Chemical Formula

C₂₇H₄₈O₅

Average Molecular Weight

452.667

Monoisotopic Molecular Weight

452.350174646

IUPAC Name

(1S,2S,5R,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

Traditional Name

(1S,2S,5R,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol

CAS Registry Number

58469-95-7

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)C(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C27H48O5/c1-15(6-9-22(30)25(2,3)32)18-7-8-19-24-20(14-23(31)27(18,19)5)26(4)11-10-17(28)12-16(26)13-21(24)29/h15-24,28-32H,6-14H2,1-5H3/t15-,16?,17-,18-,19+,20+,21-,22?,23+,24+,26+,27-/m1/s1

InChI Key

NHPWQASMMFUHIZ-OOOZRTEJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five 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

Pentahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Pentahydroxy bile acid, alcohol, or derivatives
25-hydroxysteroid
24-hydroxysteroid
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000556)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000556)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000556)

Source

Endogenous

Endogenous (HMDB: HMDB0000556)

Animal

Animal (HMDB: HMDB0000556)

Exogenous

Food

Food (HMDB: HMDB0000556)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000556)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000556)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000556)

Lipid metabolism pathway (HMDB: HMDB0000556)

Cellular process

Cell signaling (HMDB: HMDB0000556)

Biochemical process

Lipid transport (HMDB: HMDB0000556)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000556)

Molecular messenger

Hormone (HMDB: HMDB0000556)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000556)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.43	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.07 m³·mol⁻¹	ChemAxon
Polarizability	54.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000556

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022116

KNApSAcK ID

Not Available

Chemspider ID

13628107

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5540

PubChem Compound

21252253

PDB ID

Not Available

ChEBI ID

172126

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Hoshita, Takahiko. Bile acids and sterols. XLVII. Synthesis of 3a,7a,12a,25x,26-and 3a,7a,12a,24x,25-pentahydroxycoprostanes. Journal of Biochemistry (Tokyo, Japan) (1962), 52 176-9.

Showing chemical card for 5b-Cholestane-3a,7a,12a,24,25-pentol (CFc000000432)

MOL for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

3D MOL for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

3D SDF for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

3D-SDF for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

PDB for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

3D PDB for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

SMILES for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

INCHI for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

Structure for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)

3D Structure for CFc000000432 (5b-Cholestane-3a,7a,12a,24,25-pentol)