IMPPAT Phytochemical information: 
Microcarpine

Microcarpine
Summary

SMILES: COc1c(OC)ccc2c1C(=O)O/C/2=C/c1c(CCN(C)C)cc2c(c1O)OCO2
InChI: InChI=1S/C22H23NO7/c1-23(2)8-7-12-9-17-21(29-11-28-17)19(24)14(12)10-16-13-5-6-15(26-3)20(27-4)18(13)22(25)30-16/h5-6,9-10,24H,7-8,11H2,1-4H3/b16-10+
InChIKey: JUQYFQUYIWWESV-MHWRWJLKSA-N
DeepSMILES: COccOC))cccc6C=O)O/C/5=C/ccCCNC)C))))cccc6O))OCO5
Scaffold Graph/Node/Bond level: O=C1OC(=Cc2ccc3c(c2)OCO3)c2ccccc21
Scaffold Graph/Node level: OC1OC(CC2CCC3OCOC3C2)C2CCCCC12
Scaffold Graph level: CC1CC(CC2CCC3CCCC3C2)C2CCCCC12
Functional groups: cOC; c/C=C1\ccC(=O)O1; CN(C)C; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isocoumarans
ClassyFire Subclass: Isobenzofuranones
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
microcarpine
External chemical identifiers:
CID:CID_54611245
Chemical structure download


Microcarpine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 413.43
Log P RDKit 2.91
Topological polar surface area (Å2) RDKit 86.69
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Microcarpine
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.723803


Microcarpine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.57
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No