IMPPAT Phytochemical information: 
Sappanol

Sappanol
Summary

SMILES: Oc1ccc2c(c1)OC[C@]([C@H]2O)(O)Cc1ccc(c(c1)O)O
InChI: InChI=1S/C16H16O6/c17-10-2-3-11-14(6-10)22-8-16(21,15(11)20)7-9-1-4-12(18)13(19)5-9/h1-6,15,17-21H,7-8H2/t15-,16+/m0/s1
InChIKey: MPGFEHZDABUJFR-JKSUJKDBSA-N
DeepSMILES: Occcccc6)OC[C@][C@H]6O))O)Ccccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccc(CC2COc3ccccc3C2)cc1
Scaffold Graph/Node level: C1CCC(CC2COC3CCCCC3C2)CC1
Scaffold Graph level: C1CCC(CC2CCC3CCCCC3C2)CC1
Functional groups: cO; cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Homoisoflavonoids
ClassyFire Subclass: Homoisoflavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavandiols (Leucoanthocyanidins)
Synonymous chemical names:
Sappanol, sappanol
External chemical identifiers:
CID:CID_13846649; ChEMBL:CHEMBL477779; ZINC:ZINC000013481874; SureChEMBL:SCHEMBL166681; MolPort-000-881-238
Chemical structure download


Sappanol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 304.3
Log P RDKit 1.2
Topological polar surface area (Å2) RDKit 110.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Sappanol
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.53


Sappanol
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 -7.51
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
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