IMPPAT Phytochemical information: 
Mecambrine

Mecambrine
Summary

SMILES: O=C1C=CC2(C=C1)C[C@H]1c3c2c2OCOc2cc3CCN1C
InChI: InChI=1S/C18H17NO3/c1-19-7-4-11-8-14-17(22-10-21-14)16-15(11)13(19)9-18(16)5-2-12(20)3-6-18/h2-3,5-6,8,13H,4,7,9-10H2,1H3/t13-/m0/s1
InChIKey: NMVDXQMYKKNYFO-ZDUSSCGKSA-N
DeepSMILES: O=CC=CCC=C6))C[C@H]cc5cOCOc5cc9CCN%13C
Scaffold Graph/Node/Bond level: O=C1C=CC2(C=C1)CC1NCCc3cc4c(c2c31)OCO4
Scaffold Graph/Node level: OC1CCC2(CC1)CC1NCCC3CC4OCOC4C2C31
Scaffold Graph level: CC1CCC2(CC1)CC1CCCC3CC4CCCC4C2C31
Functional groups: O=C1C=CCC=C1; c1cOCO1; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Proaporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
mecambrine
External chemical identifiers:
CID:CID_121336; ChEBI:CHEBI:6705
Chemical structure download


Mecambrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 295.34
Log P RDKit 2.28
Topological polar surface area (Å2) RDKit 38.77
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.39
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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


Mecambrine
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 0.74


Mecambrine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.39
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No