IMPPAT Phytochemical information: 
sappanone B

sappanone B
Summary

SMILES: Oc1ccc2c(c1)OC[C@](C2=O)(O)Cc1ccc(c(c1)O)O
InChI: InChI=1S/C16H14O6/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/h1-6,17-19,21H,7-8H2/t16-/m1/s1
InChIKey: BTLMXNHNFFXBHW-MRXNPFEDSA-N
DeepSMILES: Occcccc6)OC[C@]C6=O))O)Ccccccc6)O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2OCC1Cc1ccccc1
Scaffold Graph/Node level: OC1C(CC2CCCCC2)COC2CCCCC21
Scaffold Graph level: CC1C(CC2CCCCC2)CCC2CCCCC21
Functional groups: cO; cOC; cC(=O)C; 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: Isoflavonoids
NP Classifier Class: Isoflavanones
Synonymous chemical names:
sappanone-b
External chemical identifiers:
CID:CID_13888976; ChEMBL:CHEMBL477778; SureChEMBL:SCHEMBL13982626
Chemical structure download


sappanone B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 302.28
Log P RDKit 1.35
Topological polar surface area (Å2) RDKit 107.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
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 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.19
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


sappanone B
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 0.62


sappanone B
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 -7.05
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