IMPPAT Phytochemical information: 
Amurensine

Amurensine
Summary

SMILES: COc1cc2C[C@@H]3N(C[C@H](c2cc1O)c1c3cc2c(c1)OCO2)C
InChI: InChI=1S/C19H19NO4/c1-20-8-14-11-5-16(21)17(22-2)4-10(11)3-15(20)13-7-19-18(6-12(13)14)23-9-24-19/h4-7,14-15,21H,3,8-9H2,1-2H3/t14-,15+/m1/s1
InChIKey: BXWVSGUITWLTOD-CABCVRRESA-N
DeepSMILES: COcccC[C@@H]NC[C@H]c7cc%11O))))cc6cccc6)OCO5))))))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1NCC2c2cc3c(cc21)OCO3
Scaffold Graph/Node level: C1CCC2C(C1)CC1NCC2C2CC3OCOC3CC12
Scaffold Graph level: C1CC2CC3C4CCC(C5CCCCC5C4)C3CC2C1
Functional groups: cOC; CN(C)C; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Dibenzocycloheptenes
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
amurensine
External chemical identifiers:
CID:CID_442164; ChEBI:CHEBI:2688
Chemical structure download


Amurensine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 325.36
Log P RDKit 2.8
Topological polar surface area (Å2) RDKit 51.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6


Amurensine
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 0.87


Amurensine
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 -6.34
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes