IMPPAT Phytochemical information: 
Cyclolinopeptide B
Cyclolinopeptide B
Summary

SMILES: CSCC[C@@H]1NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H]2N(C(=O)[C@H]3N(C(=O)[C@@H](NC(=O)[C@@H](NC1=O)CC(C)C)[C@H](CC)C)CCC3)CCC2)C(C)C)[C@H](CC)C
InChI: InChI=1S/C56H83N9O9S/c1-10-35(7)46-54(72)57-39(26-29-75-9)48(66)58-40(30-33(3)4)50(68)63-47(36(8)11-2)56(74)65-28-19-25-44(65)55(73)64-27-18-24-43(64)52(70)60-41(31-37-20-14-12-15-21-37)49(67)59-42(32-38-22-16-13-17-23-38)51(69)61-45(34(5)6)53(71)62-46/h12-17,20-23,33-36,39-47H,10-11,18-19,24-32H2,1-9H3,(H,57,72)(H,58,66)(H,59,67)(H,60,70)(H,61,69)(H,62,71)(H,63,68)/t35-,36-,39-,40-,41-,42-,43-,44-,45-,46-,47-/m0/s1
InChIKey: BRDMGDLQYNAXNM-NGFONASMSA-N
DeepSMILES: CSCC[C@@H]NC=O)[C@@H]NC=O)[C@@H]NC=O)[C@H]Ccccccc6)))))))NC=O)[C@H]Ccccccc6)))))))NC=O)[C@H]NC=O)[C@H]NC=O)[C@@H]NC=O)[C@@H]NC%27=O)))CCC)C))))))[C@H]CC))C))))CCC5))))))CCC5)))))))))))))CC)C)))))[C@H]CC))C
Scaffold Graph/Node/Bond level: O=C1CNC(=O)CNC(=O)CNC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccccc2)NC(=O)C2CCCN2C(=O)C2CCCN2C(=O)CNC(=O)CN1
Scaffold Graph/Node level: OC1CNC(O)CNC(O)CNC(O)C(CC2CCCCC2)NC(O)C(CC2CCCCC2)NC(O)C2CCCN2C(O)C2CCCN2C(O)CNC(O)CN1
Scaffold Graph level: CC1CCC(C)CCC(C)CCC(C)C2CCCC2C(C)C2CCCC2C(C)CC(CC2CCCCC2)C(C)CC(CC2CCCCC2)C(C)CCC(C)CC1
Functional groups: CSC; CNC(=O)C; CN(C)C(=O)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:
cyclolinopeptide b
External chemical identifiers:
CID:CID_10581956
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cyclolinopeptide B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1058.4
Log P RDKit 3.41
Topological polar surface area (Å2) RDKit 244.32
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 56
Number of heavy atoms RDKit 75
Number of heteroatoms RDKit 19
Number of nitrogen atoms RDKit 9
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 35
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 5
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
Cyclolinopeptide B
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.145488
Cyclolinopeptide B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Insoluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.73
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