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:CID_108052; ChEMBL:CHEMBL1407645; ChEBI: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 316.44
Log P RDKit 3.64
Topological polar surface area (Å2) RDKit 53.6
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
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 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 1
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
Cafestol
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.831482
Cafestol
ADME 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 -5.90
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
Cafestol
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000376943BCL2L11784
ENSP00000329623BCL2828
ENSP00000311032CASP3700
ENSP00000358022MCL1933
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.