IMPPAT Phytochemical information: 
(S)-Nandigerine
(S)-Nandigerine
Summary

SMILES: COc1c(O)ccc2c1-c1c3C(C2)NCCc3cc2c1OCO2
InChI: InChI=1S/C18H17NO4/c1-21-17-12(20)3-2-9-6-11-14-10(4-5-19-11)7-13-18(23-8-22-13)16(14)15(9)17/h2-3,7,11,19-20H,4-6,8H2,1H3
InChIKey: CFUKKPQRQGCLAT-UHFFFAOYSA-N
DeepSMILES: COccO)cccc6-ccCC6)NCCc6ccc%10OCO5
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1NCCc3cc4c(c-2c31)OCO4
Scaffold Graph/Node level: C1CCC2C(C1)CC1NCCC3CC4OCOC4C2C31
Scaffold Graph level: C1CCC2C(C1)CC1CCCC3CC4CCCC4C2C13
Functional groups: cOC; cO; CNC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids|Isoquinoline alkaloids
Synonymous chemical names:
hernangerine, (+)-nandigerine, nandigerine, (+), nandigerine
External chemical identifiers:
CID:CID_422682; ChEBI:CHEBI:174972
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(S)-Nandigerine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 311.34
Log P RDKit 2.54
Topological polar surface area (Å2) RDKit 59.95
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
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 12
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
(S)-Nandigerine
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 0.847363
(S)-Nandigerine
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 -6.46
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes