IMPPAT Phytochemical information: 
Sumatrol

Sumatrol
Summary

SMILES: COc1cc2OC[C@@H]3[C@H](c2cc1OC)C(=O)c1c(O3)c2C[C@@H](Oc2cc1O)C(=C)C
InChI: InChI=1S/C23H22O7/c1-10(2)14-6-12-16(29-14)7-13(24)21-22(25)20-11-5-17(26-3)18(27-4)8-15(11)28-9-19(20)30-23(12)21/h5,7-8,14,19-20,24H,1,6,9H2,2-4H3/t14-,19-,20+/m1/s1
InChIKey: ZPEHYKMRUBEPSQ-XMCHAPAWSA-N
DeepSMILES: COcccOC[C@@H][C@H]c6cc%10OC)))))C=O)ccO6)cC[C@@H]Oc5cc9O)))))C=C)C
Scaffold Graph/Node/Bond level: O=C1c2ccc3c(c2OC2COc4ccccc4C12)CCO3
Scaffold Graph/Node level: OC1C2CCC3OCCC3C2OC2COC3CCCCC3C21
Scaffold Graph level: CC1C2CCC3CCCC3C2CC2CCC3CCCCC3C21
Functional groups: cOC; cC(=O)C; cO; C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Rotenoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavanones|Rotenoids
Synonymous chemical names:
Sumatrol, sumatrol
External chemical identifiers:
CID:CID_442824; ChEMBL:CHEMBL518045; ChEBI:CHEBI:9358; ZINC:ZINC000003979083; FDASRS:69G1LPQ7X0; SureChEMBL:SCHEMBL4739987
Chemical structure download


Sumatrol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 410.42
Log P RDKit 3.41
Topological polar surface area (Å2) RDKit 83.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
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 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 3
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Sumatrol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.776624


Sumatrol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.75
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No