IMPPAT Phytochemical information: 
16-O-Methylcafestol

16-O-Methylcafestol
Summary

SMILES: CO[C@]1(CO)C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)c2ccoc2CC1)C
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
InChIKey: BDVVNPOGDNWUOI-GVOJMRIRSA-N
DeepSMILES: CO[C@]CO))C[C@]C[C@H]5CC[C@H]6[C@][C@H]CC%10))cccoc5CC9))))))))C
Scaffold Graph/Node/Bond level: c1cc2c(o1)CCC1C2CCC23CCC(CCC12)C3
Scaffold Graph/Node level: C1CC2C(CCC3C2CCC24CCC(CCC32)C4)O1
Scaffold Graph level: C1CC2CCC3C(CCC45CCC(CCC34)C5)C2C1
Functional groups: COC; coc; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthofurans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Kaurane and Phyllocladane diterpenoids|Norkaurane diterpenoids
Synonymous chemical names:
16-o-methylcafestol, 10-o-methylcafestol
External chemical identifiers:
CID:CID_68103163; ZINC:ZINC000071769612; SureChEMBL:SCHEMBL10307383; MolPort-044-561-683
Chemical structure download


16-O-Methylcafestol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 330.47
Log P RDKit 4.29
Topological polar surface area (Å2) RDKit 42.6
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.81
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


16-O-Methylcafestol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.879243


16-O-Methylcafestol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes