IMPPAT Phytochemical information: 
16-Oxoprometaphanine
16-Oxoprometaphanine
Summary

SMILES: COC1=CC[C@@]23[C@](C1=O)(C[C@@H](c1c3c(OC)c(cc1)OC)O)N(C)C(=O)C2
InChI: InChI=1S/C20H23NO6/c1-21-15(23)10-19-8-7-14(26-3)18(24)20(19,21)9-12(22)11-5-6-13(25-2)17(27-4)16(11)19/h5-7,12,22H,8-10H2,1-4H3/t12-,19+,20+/m0/s1
InChIKey: ZLACZJGCNXVIAX-NXXCRTJYSA-N
DeepSMILES: COC=CC[C@][C@]C6=O))C[C@@H]cc6cOC))ccc6))OC))))))O)))NC)C=O)C5
Scaffold Graph/Node/Bond level: O=C1CC23CC=CC(=O)C2(CCc2ccccc23)N1
Scaffold Graph/Node level: OC1CC23CCCC(O)C2(CCC2CCCCC23)N1
Scaffold Graph level: CC1CC23CCC4CCCCC4C2(CCCC3C)C1
Functional groups: CC=C(OC)C(=O)C; cOC; CO; CC(=O)N(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Hasubanan alkaloids
Synonymous chemical names:
16-oxoprometaphanine, 16-oxoprotometaphanine
External chemical identifiers:
CID:CID_91895298; ZINC:ZINC000095914142; MolPort-035-705-742
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
16-Oxoprometaphanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 373.41
Log P RDKit 1.48
Topological polar surface area (Å2) RDKit 85.3
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
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 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
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 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
16-Oxoprometaphanine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.86
16-Oxoprometaphanine
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 -7.97
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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 Yes