IMPPAT Phytochemical information: 
Cafestol
Cafestol
Summary

SMILES: OC[C@@]1(O)C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)c2ccoc2CC1)C
InChI: InChI=1S/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
InChIKey: DNJVYWXIDISQRD-HWUKTEKMSA-N
DeepSMILES: OC[C@@]O)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: CO; coc
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: Norkaurane diterpenoids
Synonymous chemical names:
cafestol
External chemical identifiers:
CID:108052; ChEMBL:CHEMBL1407645; ChEBI:3291; ZINC:ZINC000004097876; FDASRS:AC465T6Q6W; SureChEMBL:SCHEMBL93865; MolPort-044-561-186
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cafestol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Cafestol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.83
Cafestol
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -5.9
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
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
Cafestol
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000311032CASP3700
ENSP00000329623BCL2828
ENSP00000358022MCL1933
ENSP00000376943BCL2L11784
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.