1.0 2010-04-08 22:06:33 UTC 2025-11-18 22:58:23 UTC FDB005152 16-O-Methylcafestol 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. 10-O-METHYLCAFESTOL C21H30O3 330.4611 330.219494826 [(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 [(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 CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3 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 BDVVNPOGDNWUOI-GVOJMRIRSA-N 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. Naphthofurans Organic compounds Organoheterocyclic compounds Naphthofurans Aromatic heteropolycyclic compounds Benzofurans Dialkyl ethers Furans Heteroaromatic compounds Hydrocarbon derivatives Oxacyclic compounds Primary alcohols Alcohol Aromatic heteropolycyclic compound Benzofuran Dialkyl ether Ether Furan Heteroaromatic compound Hydrocarbon derivative Naphthofuran Organic oxygen compound Organooxygen compound Oxacycle Primary alcohol logp 3.64 ALOGPS logs -4.66 ALOGPS solubility 7.30e-03 g/l ALOGPS logp 3.32 ChemAxon pka_strongest_acidic 14.36 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac [(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 ChemAxon average_mass 330.4611 ChemAxon mono_mass 330.219494826 ChemAxon smiles CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3 ChemAxon formula C21H30O3 ChemAxon inchi 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 ChemAxon inchikey BDVVNPOGDNWUOI-GVOJMRIRSA-N ChemAxon polar_surface_area 42.6 ChemAxon refractivity 93.3 ChemAxon polarizability 38.31 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 48834 Specdb::MsMs 48835 Specdb::MsMs 48836 Specdb::MsMs 162042 Specdb::MsMs 162043 Specdb::MsMs 162044 Specdb::MsMs 3601424 Specdb::MsMs 3601425 Specdb::MsMs 3601426 Specdb::MsMs 3601427 Specdb::MsMs 3601428 Specdb::MsMs 3601429 Arabica coffee Type 1 specific Coffea arabica 13443 Robusta coffee Type 1 specific Coffea canephora 49390