IMPPAT Phytochemical information: 
Hippeastrine

Hippeastrine
Summary

SMILES: CN1CCC2=C[C@@H]([C@@H]3[C@H]([C@H]12)c1cc2OCOc2cc1C(=O)O3)O
InChI: InChI=1S/C17H17NO5/c1-18-3-2-8-4-11(19)16-14(15(8)18)9-5-12-13(22-7-21-12)6-10(9)17(20)23-16/h4-6,11,14-16,19H,2-3,7H2,1H3/t11-,14-,15+,16+/m0/s1
InChIKey: DGQPIOQRPAGNGB-DANNLKNASA-N
DeepSMILES: CNCCC=C[C@@H][C@@H][C@H][C@H]96)cccOCOc5cc9C=O)O%13)))))))))))))O
Scaffold Graph/Node/Bond level: O=C1OC2CC=C3CCNC3C2c2cc3c(cc21)OCO3
Scaffold Graph/Node level: OC1OC2CCC3CCNC3C2C2CC3OCOC3CC12
Scaffold Graph level: CC1CC2CCC3CCCC3C2C2CC3CCCC3CC12
Functional groups: CN(C)C; CC(=CC)C; c1cOCO1; cC(=O)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Homolycorine-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
hippeastrine
External chemical identifiers:
CID:CID_441594; ChEMBL:CHEMBL457606; ChEBI:CHEBI:5724; ZINC:ZINC000053276060; SureChEMBL:SCHEMBL4278126
Chemical structure download


Hippeastrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 315.33
Log P RDKit 1.04
Topological polar surface area (Å2) RDKit 68.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Hippeastrine
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 0.57


Hippeastrine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.71
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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