IMPPAT Phytochemical information: 
Nitrotyrasanguinarine
Nitrotyrasanguinarine
Summary

SMILES: Oc1ccc(cc1)CC(C1c2c3OCOc3ccc2-c2c(N1C)c1cc3OCOc3cc1cc2)[N+](=O)[O-]
InChI: InChI=1S/C28H22N2O7/c1-29-26-19(7-4-16-11-23-24(12-20(16)26)36-13-35-23)18-8-9-22-28(37-14-34-22)25(18)27(29)21(30(32)33)10-15-2-5-17(31)6-3-15/h2-9,11-12,21,27,31H,10,13-14H2,1H3
InChIKey: RKBDQFXCPXWLKG-UHFFFAOYSA-N
DeepSMILES: Occcccc6))CCCccOCOc5ccc9-ccN%13C))cccOCOc5cc9cc%13)))))))))))))))))))))))[N+]=O)[O-]
Scaffold Graph/Node/Bond level: c1ccc(CCC2Nc3c(ccc4cc5c(cc34)OCO5)-c3ccc4c(c32)OCO4)cc1
Scaffold Graph/Node level: C1CCC(CCC2NC3C4CC5OCOC5CC4CCC3C3CCC4OCOC4C23)CC1
Scaffold Graph level: C1CCC(CCC2CC3C4CC5CCCC5CC4CCC3C3CCC4CCCC4C23)CC1
Functional groups: cO; C[N+](=O)[O-]; c1cOCO1; cN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Benzophenanthridine alkaloids
ClassyFire Subclass: Dihydrobenzophenanthridine alkaloids
Synonymous chemical names:
nitrotyrasanguinarine
External chemical identifiers:
CID:CID_180206
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Nitrotyrasanguinarine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 498.49
Log P RDKit 5.05
Topological polar surface area (Å2) RDKit 103.53
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 22
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 7
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 7
Nitrotyrasanguinarine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.31
Nitrotyrasanguinarine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.37
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes