IMPPAT Phytochemical information: 
1H-Indole-3-carboxylic acid, 5-methoxy-, methyl ester

1H-Indole-3-carboxylic acid, 5-methoxy-, methyl ester
Summary

SMILES: OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C\1/C(=COC1=O)O)C
InChI: InChI=1S/C20H28O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,10,14,16-17,21-23H,1,4,6-9,11H2,2-3H3/b13-5-/t14-,16+,17-,19+,20+/m1/s1
InChIKey: QQCLBMUOIGPCDE-MCQYLCLSSA-N
DeepSMILES: OC[C@]C)[C@H]O)CC[C@@][C@@H]6CCC=C)[C@H]6C/C=C/C=COC/5=O))))O))))))))))C
Scaffold Graph/Node/Bond level: C=C1CCC2CCCCC2C1CC=C1C=COC1=O
Scaffold Graph/Node level: CC1CCC2CCCCC2C1CCC1CCOC1O
Scaffold Graph level: CC1CCCC1CCC1C(C)CCC2CCCCC21
Functional groups: CO; C=C(C)C; C/C=C1\C(=O)OC=C1O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Dihydrofurans
ClassyFire Subclass: Furanones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids
Synonymous chemical names:
14-deoxy-11-dehydroandrographolide
External chemical identifiers:
CID:CID_15411809; ZINC:ZINC000110786817
Chemical structure download


1H-Indole-3-carboxylic acid, 5-methoxy-, methyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 348.44
Log P RDKit 3
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


1H-Indole-3-carboxylic acid, 5-methoxy-, methyl ester
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 0.41


1H-Indole-3-carboxylic acid, 5-methoxy-, methyl ester
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.48
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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