ChemFOnt: Showing chemical card for 16-O-Methylcafestol (CFc000282076)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:05 UTC

Chemfont ID

CFc000282076

Molecule Identification

Common Name

16-O-Methylcafestol

Definition

16-o-methylcafestol, also known as 16-omc compound, is a member of the class of compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 16-o-methylcafestol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 16-o-methylcafestol can be found in arabica coffee, which makes 16-o-methylcafestol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
16-OMC compound	MeSH

Chemical Formula

C₂₁H₃₀O₃

Average Molecular Weight

330.4611

Monoisotopic Molecular Weight

330.219494826

IUPAC Name

[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methanol

Traditional Name

[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methanol

CAS Registry Number

None

SMILES

CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3

InChI Identifier

InChI=1S/C21H30O3/c1-19-8-6-17-15(7-10-24-17)16(19)5-9-20-11-14(3-4-18(19)20)21(12-20,13-22)23-2/h7,10,14,16,18,22H,3-6,8-9,11-13H2,1-2H3/t14-,16-,18+,19-,20+,21+/m1/s1

InChI Key

BDVVNPOGDNWUOI-GVOJMRIRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Benzofuran
Heteroaromatic compound
Furan
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302560)

Food

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	3.64	ALOGPS
logP	3.32	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.3 m³·mol⁻¹	ChemAxon
Polarizability	38.31 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302560

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005152

KNApSAcK ID

Not Available

Chemspider ID

22901058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

16-O-Methylcafestol

METLIN ID

Not Available

PubChem Compound

68103163

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 16-O-Methylcafestol (CFc000282076)

MOL for CFc000282076 (16-O-Methylcafestol)

3D MOL for CFc000282076 (16-O-Methylcafestol)

3D SDF for CFc000282076 (16-O-Methylcafestol)

3D-SDF for CFc000282076 (16-O-Methylcafestol)

PDB for CFc000282076 (16-O-Methylcafestol)

3D PDB for CFc000282076 (16-O-Methylcafestol)

SMILES for CFc000282076 (16-O-Methylcafestol)

INCHI for CFc000282076 (16-O-Methylcafestol)

Structure for CFc000282076 (16-O-Methylcafestol)

3D Structure for CFc000282076 (16-O-Methylcafestol)