ChemFOnt: Showing chemical card for Coriandrinol (CFc000282085)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:06 UTC

Chemfont ID

CFc000282085

Molecule Identification

Common Name

Coriandrinol

Definition

Coriandrinol belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Coriandrinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Coriandrinol can be found in coriander, which makes coriandrinol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-Sitosterol glucutonide	MeSH
beta-Sitosterol glucoside	MeSH
beta-Sitosterol-beta-D-glycoside	MeSH
Daucosterol	MeSH
Lyoniside	MeSH
Sitosterol beta-D-glucoside	MeSH
beta-Sitosteryl-beta-D-glucopyranoside	MeSH
Eleutheroside a	MeSH
Sitosterol glucuronide	MeSH

Chemical Formula

C₃₅H₆₀O₆

Average Molecular Weight

576.859

Monoisotopic Molecular Weight

576.438989652

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,10S,11S,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,10S,11S,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

474-58-8

SMILES

[H][C@@](C)(CC[C@@]([H])(CC)C(C)C)C1([H])CC[C@@]2([H])[C@]3([H])CC=C4CC([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24?,25+,26?,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1

InChI Key

NPJICTMALKLTFW-QYDWNGEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Triterpenoid
Stigmastane-skeleton
Steroidal glycoside
Delta-5-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302569)

Food

Herb and spice

Herb

Coriander (FooDB: FOOD00061)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0028 g/L	ALOGPS
logP	5.71	ALOGPS
logP	6.07	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	162.18 m³·mol⁻¹	ChemAxon
Polarizability	69.48 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

HMDB0302569

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005190

KNApSAcK ID

Not Available

Chemspider ID

64693

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71628

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Coriandrinol (CFc000282085)

MOL for CFc000282085 (Coriandrinol)

3D MOL for CFc000282085 (Coriandrinol)

3D SDF for CFc000282085 (Coriandrinol)

3D-SDF for CFc000282085 (Coriandrinol)

PDB for CFc000282085 (Coriandrinol)

3D PDB for CFc000282085 (Coriandrinol)

SMILES for CFc000282085 (Coriandrinol)

INCHI for CFc000282085 (Coriandrinol)

Structure for CFc000282085 (Coriandrinol)

3D Structure for CFc000282085 (Coriandrinol)