IMPPAT Phytochemical information: 
(2,3,4,5,6-pentahydroxycyclohexyl) 2-(1H-indol-3-yl)acetate

(2,3,4,5,6-pentahydroxycyclohexyl) 2-(1H-indol-3-yl)acetate
Summary

SMILES: O=C(Cc1c[nH]c2c1cccc2)OC1C(O)C(O)C(C(C1O)O)O
InChI: InChI=1S/C16H19NO7/c18-10(5-7-6-17-9-4-2-1-3-8(7)9)24-16-14(22)12(20)11(19)13(21)15(16)23/h1-4,6,11-17,19-23H,5H2
InChIKey: XUACNUJFOIKYPQ-UHFFFAOYSA-N
DeepSMILES: O=CCcc[nH]cc5cccc6))))))))))OCCO)CO)CCC6O))O))O
Scaffold Graph/Node/Bond level: O=C(Cc1c[nH]c2ccccc12)OC1CCCCC1
Scaffold Graph/Node level: OC(CC1CNC2CCCCC12)OC1CCCCC1
Scaffold Graph level: CC(CC1CCCCC1)CC1CCC2CCCCC21
Functional groups: COC(C)=O; c[nH]c; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indolyl carboxylic acids and derivatives
Synonymous chemical names:
iaa myoinositol
External chemical identifiers:
CID:CID_152656
Chemical structure download


(2,3,4,5,6-pentahydroxycyclohexyl) 2-(1H-indol-3-yl)acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 337.33
Log P RDKit -1.56
Topological polar surface area (Å2) RDKit 143.24
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 4
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


(2,3,4,5,6-pentahydroxycyclohexyl) 2-(1H-indol-3-yl)acetate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.37


(2,3,4,5,6-pentahydroxycyclohexyl) 2-(1H-indol-3-yl)acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No