IMPPAT Phytochemical information: 
Citrusin I
Citrusin I
Summary

SMILES: CC[C@@H]([C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC1=O)C)[C@H](O)C)[C@H](O)C)C
InChI: InChI=1S/C34H53N7O9/c1-8-18(4)26-33(49)36-19(5)29(45)41-27(20(6)42)32(48)35-16-25(44)39-28(21(7)43)34(50)38-24(15-22-12-10-9-11-13-22)30(46)37-23(14-17(2)3)31(47)40-26/h9-13,17-21,23-24,26-28,42-43H,8,14-16H2,1-7H3,(H,35,48)(H,36,49)(H,37,46)(H,38,50)(H,39,44)(H,40,47)(H,41,45)/t18-,19-,20+,21+,23-,24-,26-,27-,28-/m0/s1
InChIKey: LZVXYGLCVNPQDY-ITUDXDSCSA-N
DeepSMILES: CC[C@@H][C@@H]NC=O)[C@H]CCC)C)))NC=O)[C@H]Ccccccc6)))))))NC=O)[C@@H]NC=O)CNC=O)[C@@H]NC=O)[C@@H]NC%21=O)))C))))[C@H]O)C))))))))[C@H]O)C))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CNC(=O)CNC(=O)CNC(=O)C(Cc2ccccc2)NC(=O)CNC(=O)CNC(=O)CN1
Scaffold Graph/Node level: OC1CNC(O)CNC(O)CNC(O)C(CC2CCCCC2)NC(O)CNC(O)CNC(O)CN1
Scaffold Graph level: CC1CCC(C)CCC(C)CCC(C)CC(CC2CCCCC2)C(C)CCC(C)CCC(C)CC1
Functional groups: CNC(=O)C; CC(=O)NC; CO
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 i
External chemical identifiers:
CID:CID_15232519; ZINC:ZINC000238762630
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Citrusin I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 703.84
Log P RDKit -1.86
Topological polar surface area (Å2) RDKit 244.16
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 50
Number of heteroatoms RDKit 16
Number of nitrogen atoms RDKit 7
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2
Citrusin I
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 4
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 0.147262
Citrusin I
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 -9.23
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