IMPPAT Phytochemical information: 
Rugosanine B
Rugosanine B
Summary

SMILES: COc1ccc2cc1/C=C\NC(=O)C(Cc1ccccc1)NC(=O)C1C(O2)CCN1C(=O)C(N(C)C)Cc1cc2c([nH]1)cccc2
InChI: InChI=1S/C36H39N5O5/c1-40(2)30(22-26-20-24-11-7-8-12-28(24)38-26)36(44)41-18-16-32-33(41)35(43)39-29(19-23-9-5-4-6-10-23)34(42)37-17-15-25-21-27(46-32)13-14-31(25)45-3/h4-15,17,20-21,29-30,32-33,38H,16,18-19,22H2,1-3H3,(H,37,42)(H,39,43)/b17-15-
InChIKey: WEFMVTTVBXAYDD-ICFOKQHNSA-N
DeepSMILES: COcccccc6/C=C\NC=O)CCcccccc6)))))))NC=O)CCO%13)CCN5C=O)CNC)C))Ccccc[nH]5)cccc6
Scaffold Graph/Node/Bond level: O=C1NC=Cc2cccc(c2)OC2CCN(C(=O)CCc3cc4ccccc4[nH]3)C2C(=O)NC1Cc1ccccc1
Scaffold Graph/Node level: OC1NCCC2CCCC(C2)OC2CCN(C(O)CCC3CC4CCCCC4N3)C2C(O)NC1CC1CCCCC1
Scaffold Graph level: CC1CCCC2CCCC(C2)CC2CCC(C(C)CCC3CC4CCCCC4C3)C2C(C)CC1CC1CCCCC1
Functional groups: cOC; CN(C)C; c/C=C\NC(=O)C; c[nH]c; CNC(=O)C; CC(=O)N(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Alkaloids|Amino acids and Peptides
NP Classifier Superclass: Peptide alkaloids
NP Classifier Class: Ansa peptide alkaloids
Synonymous chemical names:
rugosanine b, Rugosanine B
External chemical identifiers:
CID:CID_102151885
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rugosanine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 621.74
Log P RDKit 3.53
Topological polar surface area (Å2) RDKit 116
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 25
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.31
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6
Rugosanine B
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 3
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 0.29
Rugosanine B
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 -6.81
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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