IMPPAT Phytochemical information: 
Citrusin II
Citrusin II
Summary

SMILES: O=C1CNC(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@H]3N(C(=O)CN1)CCC3)C)CCC2)Cc1c[nH]c2c1cccc2
InChI: InChI=1S/C37H44N8O7/c1-22-37(52)45-16-8-14-30(45)36(51)43-27(17-23-9-3-2-4-10-23)34(49)42-28(18-24-19-38-26-12-6-5-11-25(24)26)33(48)40-20-31(46)39-21-32(47)44-15-7-13-29(44)35(50)41-22/h2-6,9-12,19,22,27-30,38H,7-8,13-18,20-21H2,1H3,(H,39,46)(H,40,48)(H,41,50)(H,42,49)(H,43,51)/t22-,27-,28-,29-,30-/m0/s1
InChIKey: QRRCCRJORDBZGC-NELKFLMZSA-N
DeepSMILES: O=CCNC=O)[C@@H]NC=O)[C@H]Ccccccc6)))))))NC=O)[C@H]NC=O)[C@@H]NC=O)[C@H]NC=O)CN%21)))CCC5)))))))C)))CCC5))))))))))Ccc[nH]cc5cccc6
Scaffold Graph/Node/Bond level: O=C1CNC(=O)C(Cc2c[nH]c3ccccc23)NC(=O)C(Cc2ccccc2)NC(=O)C2CCCN2C(=O)CNC(=O)C2CCCN2C(=O)CN1
Scaffold Graph/Node level: OC1CNC(O)C(CC2CNC3CCCCC23)NC(O)C(CC2CCCCC2)NC(O)C2CCCN2C(O)CNC(O)C2CCCN2C(O)CN1
Scaffold Graph level: CC1CCC(C)C(CC2CCC3CCCCC32)CC(C)C(CC2CCCCC2)CC(C)C2CCCC2C(C)CCC(C)C2CCCC2C(C)CC1
Functional groups: CNC(=O)C; CN(C)C(=O)C; CC(=O)N(C)C; c[nH]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: Amino acids and Peptides
NP Classifier Superclass: Oligopeptides
NP Classifier Class: Cyclic peptides
Synonymous chemical names:
citrusin ii
External chemical identifiers:
CID:CID_102082877; ZINC:ZINC000238736070
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Citrusin II
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 712.81
Log P RDKit -0.34
Topological polar surface area (Å2) RDKit 201.91
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 52
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 8
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Citrusin II
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21237
Citrusin II
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.70
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 Yes
P-glycoprotein substrate SwissADME Yes