IMPPAT Phytochemical information: 
Aspidofractinine-3-carboxylic acid, methyl ester, (2alpha,3beta,5alpha)-

Aspidofractinine-3-carboxylic acid, methyl ester, (2alpha,3beta,5alpha)-
Summary

SMILES: COC(=O)[C@@H]1C[C@@]23CCCN4C3[C@@]3([C@]1(CC2)Nc1c3cccc1)CC4
InChI: InChI=1S/C21H26N2O2/c1-25-17(24)15-13-19-7-4-11-23-12-10-20(18(19)23)14-5-2-3-6-16(14)22-21(15,20)9-8-19/h2-3,5-6,15,18,22H,4,7-13H2,1H3/t15-,18?,19+,20+,21+/m0/s1
InChIKey: IYLRRIUNGGQRTN-GKCDKPGPSA-N
DeepSMILES: COC=O)[C@@H]C[C@]CCCNC6[C@@][C@]%10CC%10))Ncc5cccc6))))))))CC5
Scaffold Graph/Node/Bond level: c1ccc2c(c1)NC13CCC4(CCCN5CCC21C54)CC3
Scaffold Graph/Node level: C1CCC2C(C1)NC13CCC4(CCCN5CCC21C54)CC3
Scaffold Graph level: C1CCC2C(C1)CC13CCC4(CCCC5CCC21C54)CC3
Functional groups: COC(C)=O; CN(C)C; cNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidofractine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
kopsinine, Kopsinine
External chemical identifiers:
CID:CID_160525
Chemical structure download


Aspidofractinine-3-carboxylic acid, methyl ester, (2alpha,3beta,5alpha)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.45
Log P RDKit 2.93
Topological polar surface area (Å2) RDKit 41.57
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Aspidofractinine-3-carboxylic acid, methyl ester, (2alpha,3beta,5alpha)-
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 0.799637


Aspidofractinine-3-carboxylic acid, methyl ester, (2alpha,3beta,5alpha)-
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 -6.28
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 No