16-O-Methylcafestol
PubChem CID: 68103163
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| Compound Synonyms | 16-O-Methylcafestol, 108214-28-4, 16-O-METHYL-CAFESTOL, TJ95S36BVX, [(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, (3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b,11,12-Dodecahydro-7-methoxy-10b-methyl-5a,8-methano-5ah-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 5a,8-Methano-5ah-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-methoxy-10b-methyl-, (3bS,5aS,7R,8R,10aR,10bS)-, ((1S,4S,12S,13R,16R,17R)-17-Methoxy-12-methyl-8-oxapentacyclo(14.2.1.0(1,13).0(4,12).0(5,9))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, (3bS,5aS,7R,8R,10aR,10bS)-7-methoxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methano-5aH-cycloheptal(5,6)naphtho(2,1-b)furan-7-methanol, (3bS,5aS,7R,8R,10aR,10bS)-7-methoxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methano-5aH-cycloheptal[5,6]naphtho[2,1-b]furan-7-methanol, [(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0{1,13}.0{4,12}.0{5,9}]nonadeca-5(9),6-dien-17-yl]methanol, 16-OMC compound, UNII-TJ95S36BVX, SCHEMBL10307383, DTXSID30737953, IEA21428, 16-O-Methylcafestol, analytical standard, DA-49118, PD043748, HY-116056, CS-0063695, F86482, Q15220829, (3bS,5aS,7R,8R,10aR,10bS)- 7-methoxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methano- 5aH-cycloheptal[5,6]naphtho[2,1-b]furan-7-methanol, [(3bS,5aS,7R,8R,10aR,10bS)-7-Methoxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl]methanol |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 42.6 |
| Hydrogen Bond Donor Count | 1.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | C1CC2CCC3C(CCC45CCC(CCC34)C5)C2C1 |
| Np Classifier Class | Kaurane and Phyllocladane diterpenoids, Norkaurane diterpenoids |
| Deep Smiles | CO[C@]CO))C[C@]C[C@H]5CC[C@H]6[C@][C@H]CC%10))cccoc5CC9))))))))C |
| Heavy Atom Count | 24.0 |
| Classyfire Class | Naphthofurans |
| Description | 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. |
| Scaffold Graph Node Level | C1CC2C(CCC3C2CCC24CCC(CCC32)C4)O1 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 521.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;imppat_phytochem;pubchem |
| Defined Atom Stereocenter Count | 6.0 |
| 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 |
| Class | Naphthofurans |
| Veber Rule | True |
| Classyfire Superclass | Organoheterocyclic compounds |
| Xlogp | 3.8 |
| Superclass | Organoheterocyclic compounds |
| Gsk 4 400 Rule | False |
| Molecular Formula | C21H30O3 |
| Scaffold Graph Node Bond Level | c1cc2c(o1)CCC1C2CCC23CCC(CCC12)C3 |
| Inchi Key | BDVVNPOGDNWUOI-GVOJMRIRSA-N |
| Silicos It Class | Moderately soluble |
| Rotatable Bond Count | 2.0 |
| Synonyms | 10-O-METHYLCAFESTOL, 16-OMC compound, 10-o-methylcafestol, 16-o-methylcafestol |
| Esol Class | Moderately soluble |
| Functional Groups | CO, COC, coc |
| Compound Name | 16-O-Methylcafestol |
| Kingdom | Organic compounds |
| Exact Mass | 330.219 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 330.219 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 330.5 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Lipinski Rule Of 5 | True |
| 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 |
| Smiles | C[C@@]12CCC3=C([C@H]1CC[C@]45[C@H]2CC[C@H](C4)[C@](C5)(CO)OC)C=CO3 |
| Np Classifier Biosynthetic Pathway | Terpenoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Naphthofurans |
| Np Classifier Superclass | Diterpenoids |
- 1. Outgoing r'ship
FOUND_INto/from Coffea Arabica (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Coffea Canephora (Plant) Rel Props:Reference:ISBN:9788185042145