IMPPAT Phytochemical information: 
Alpinigenine

Alpinigenine
Summary

SMILES: COc1cc2CCN([C@H]3[C@H](c2cc1OC)O[C@@H](O)c1c3ccc(c1OC)OC)C
InChI: InChI=1S/C22H27NO6/c1-23-9-8-12-10-16(26-3)17(27-4)11-14(12)20-19(23)13-6-7-15(25-2)21(28-5)18(13)22(24)29-20/h6-7,10-11,19-20,22,24H,8-9H2,1-5H3/t19-,20+,22-/m1/s1
InChIKey: CJYNYVSDQZLRSG-RZUBCFFCSA-N
DeepSMILES: COcccCCN[C@H][C@H]c7cc%11OC)))))O[C@@H]O)cc6cccc6OC)))OC)))))))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)COC1c3ccccc3CCNC21
Scaffold Graph/Node level: C1CCC2C(C1)COC1C3CCCCC3CCNC21
Scaffold Graph level: C1CCC2C(C1)CCC1C3CCCCC3CCCC21
Functional groups: CN(C)C; cOC; c[C@H](O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Rhoeadine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
alpinigenin, alpinigenine
External chemical identifiers:
CID:166983
Chemical structure download


Alpinigenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 401.46
Log P RDKit 3.01
Topological polar surface area (Å2) RDKit 69.62
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 4
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


Alpinigenine
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.8445


Alpinigenine
ADMET 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 -7.25
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes