IMPPAT Phytochemical information: 
O-Methylfumarophycinol

O-Methylfumarophycinol
Summary

SMILES: COc1cc2c(cc1OC)CCN(C12Cc2c([C@@H]1O)c1OCOc1cc2)C
InChI: InChI=1S/C21H23NO5/c1-22-7-6-12-8-16(24-2)17(25-3)9-14(12)21(22)10-13-4-5-15-19(27-11-26-15)18(13)20(21)23/h4-5,8-9,20,23H,6-7,10-11H2,1-3H3/t20-,21?/m0/s1
InChIKey: QDNMFIYGVRUVCE-BGERDNNASA-N
DeepSMILES: COcccccc6OC))))CCNC6Ccc[C@@H]5O))cOCOc5cc9)))))))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCNC21Cc2ccc3c(c2C1)OCO3
Scaffold Graph/Node level: C1CCC2C(C1)CCNC21CC2CCC3OCOC3C2C1
Scaffold Graph level: C1CCC2C(C1)CCCC21CC2CCC3CCCC3C2C1
Functional groups: cOC; CN(C)C; CO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Tetrahydroisoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
(-)fumaricine
External chemical identifiers:
CID:CID_179411
Chemical structure download


O-Methylfumarophycinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 369.42
Log P RDKit 2.41
Topological polar surface area (Å2) RDKit 60.39
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


O-Methylfumarophycinol
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 0.877318


O-Methylfumarophycinol
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 -6.93
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes