IMPPAT Phytochemical information: 
(2S)-3-(1H-indol-3-yl)-2-[[2-[(1R,2R)-3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetyl]amino]propanoic acid
(2S)-3-(1H-indol-3-yl)-2-[[2-[(1R,2R)-3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetyl]amino]propanoic acid
Summary

SMILES: CC/C=C/C[C@@H]1[C@H](CCC1=O)CC(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2
InChI: InChI=1S/C23H28N2O4/c1-2-3-4-8-18-15(10-11-21(18)26)13-22(27)25-20(23(28)29)12-16-14-24-19-9-6-5-7-17(16)19/h3-7,9,14-15,18,20,24H,2,8,10-13H2,1H3,(H,25,27)(H,28,29)/b4-3+/t15-,18-,20+/m1/s1
InChIKey: OUPQEYAUNCBPDQ-KERPWAHESA-N
DeepSMILES: CC/C=C/C[C@@H][C@H]CCC5=O))))CC=O)N[C@H]C=O)O))Ccc[nH]cc5cccc6
Scaffold Graph/Node/Bond level: O=C1CCC(CC(=O)NCCc2c[nH]c3ccccc23)C1
Scaffold Graph/Node level: OC1CCC(CC(O)NCCC2CNC3CCCCC23)C1
Scaffold Graph level: CC(CCCC1CCC2CCCCC21)CC1CCC(C)C1
Functional groups: C/C=C/C; CC(=O)C; CC(=O)NC; CC(=O)O; 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
Synonymous chemical names:
n-cucurbinoyltryptophan, n-jasmonoyltryptophan
External chemical identifiers:
CID:CID_6426817
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S)-3-(1H-indol-3-yl)-2-[[2-[(1R,2R)-3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetyl]amino]propanoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 396.49
Log P RDKit 3.62
Topological polar surface area (Å2) RDKit 99.26
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
(2S)-3-(1H-indol-3-yl)-2-[[2-[(1R,2R)-3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetyl]amino]propanoic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.56
(2S)-3-(1H-indol-3-yl)-2-[[2-[(1R,2R)-3-oxo-2-[(E)-pent-2-enyl]cyclopentyl]acetyl]amino]propanoic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.02
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes