ChemFOnt: Showing chemical card for 23-O-beta-D-Glucopyranosyl-25-methyldolichosterone (CFc000281314)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:34 UTC

Chemfont ID

CFc000281314

Molecule Identification

Common Name

23-O-beta-D-Glucopyranosyl-25-methyldolichosterone

Definition

23-o-beta-d-glucopyranosyl-25-methyldolichosterone is a member of the class of compounds known as steroidal glycosides. Steroidal glycosides are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. 23-o-beta-d-glucopyranosyl-25-methyldolichosterone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 23-o-beta-d-glucopyranosyl-25-methyldolichosterone can be found in common bean, green bean, and yellow wax bean, which makes 23-o-beta-d-glucopyranosyl-25-methyldolichosterone a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
23-O-b-D-Glucopyranosyl-25-methyldolichosterone	Generator
23-O-Β-D-glucopyranosyl-25-methyldolichosterone	Generator

Chemical Formula

C₃₅H₅₈O₁₀

Average Molecular Weight

638.829

Monoisotopic Molecular Weight

638.402998076

IUPAC Name

(2R,4R,5S,7S,15S)-4,5-dihydroxy-14-[(2S,3R,4R)-3-hydroxy-6,6-dimethyl-5-methylidene-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

Traditional Name

CAS Registry Number

None

SMILES

[H][C@]12C[C@H](O)[C@H](O)C[C@]1(C)C1CC[C@]3(C)C(CCC3C1CC2=O)[C@H](C)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=C)C(C)(C)C

InChI Identifier

InChI=1S/C35H58O10/c1-16(27(40)31(17(2)33(3,4)5)45-32-30(43)29(42)28(41)26(15-36)44-32)19-8-9-20-18-12-23(37)22-13-24(38)25(39)14-35(22,7)21(18)10-11-34(19,20)6/h16,18-22,24-32,36,38-43H,2,8-15H2,1,3-7H3/t16-,18?,19?,20?,21?,22+,24-,25+,26+,27+,28+,29-,30+,31+,32-,34+,35+/m0/s1

InChI Key

NLNNWFCVCWSYSK-UOECHDJWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Ergosterol-skeleton
Ergostane-skeleton
Steroidal glycoside
Ecdysteroid
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
22-hydroxysteroid
Diterpenoid
3-hydroxysteroid
6-oxosteroid
3-alpha-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
Oxosteroid
Terpene glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Monosaccharide
Fatty acyl
Oxane
Cyclic alcohol
Ketone
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Oxacycle
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301798)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	1	ALOGPS
logP	1.76	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	165.81 m³·mol⁻¹	ChemAxon
Polarizability	70.66 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0301798

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001422

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157009757

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 23-O-beta-D-Glucopyranosyl-25-methyldolichosterone (CFc000281314)

MOL for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

3D MOL for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

3D SDF for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

3D-SDF for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

PDB for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

3D PDB for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

SMILES for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

INCHI for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

Structure for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)

3D Structure for CFc000281314 (23-O-beta-D-Glucopyranosyl-25-methyldolichosterone)