IMPPAT Phytochemical information: 
trans-Dihydronarciclasine
trans-Dihydronarciclasine
Summary

SMILES: O[C@H]1C[C@H]2[C@H]([C@@H]([C@@H]1O)O)NC(=O)c1c2cc2OCOc2c1O
InChI: InChI=1S/C14H15NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h2,5-6,9-10,12,16-19H,1,3H2,(H,15,20)/t5-,6+,9-,10-,12+/m1/s1
InChIKey: SBTGHBALOCEVOR-PUZXQUAOSA-N
DeepSMILES: O[C@H]C[C@H][C@H][C@@H][C@@H]6O))O))NC=O)cc6ccOCOc5c9O
Scaffold Graph/Node/Bond level: O=C1NC2CCCCC2c2cc3c(cc21)OCO3
Scaffold Graph/Node level: OC1NC2CCCCC2C2CC3OCOC3CC12
Scaffold Graph level: CC1CC2CCCCC2C2CC3CCCC3CC12
Functional groups: CO; c1cOCO1; cC(=O)NC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
trans-dihydronarciclasine
External chemical identifiers:
CID:101204; ChEMBL:CHEMBL464432; SureChEMBL:SCHEMBL14732745
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
trans-Dihydronarciclasine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.27
Log P RDKit -1.2
Topological polar surface area (Å2) RDKit 128.48
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
trans-Dihydronarciclasine
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4071
trans-Dihydronarciclasine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.63
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No