IMPPAT Phytochemical information: 
(3S,3aalpha,6aalpha)-3alpha,6alpha-Bis(1,3-benzodioxole-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-ol
(3S,3aalpha,6aalpha)-3alpha,6alpha-Bis(1,3-benzodioxole-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-ol
Summary

SMILES: OC1O[C@@H]([C@@H]2[C@H]1[C@H](OC2)c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2
InChI: InChI=1S/C20H18O7/c21-20-17-12(18(27-20)10-1-3-13-15(5-10)25-8-23-13)7-22-19(17)11-2-4-14-16(6-11)26-9-24-14/h1-6,12,17-21H,7-9H2/t12-,17-,18+,19+,20?/m0/s1
InChIKey: AWLJZFUREZNLGG-TWBLDSMASA-N
DeepSMILES: OCO[C@@H][C@@H][C@H]5[C@H]OC5))cccccc6)OCO5)))))))))))cccccc6)OCO5
Scaffold Graph/Node/Bond level: c1cc2c(cc1C1OCC3C(c4ccc5c(c4)OCO5)OCC13)OCO2
Scaffold Graph/Node level: C1OC2CCC(C3OCC4C3COC4C3CCC4OCOC4C3)CC2O1
Scaffold Graph level: C1CC2CCC(C3CCC4C(C5CCC6CCCC6C5)CCC34)CC2C1
Functional groups: COC(O)C; COC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Furanoid lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Furofuranoid lignans
Synonymous chemical names:
4-hydroxysesamin
External chemical identifiers:
CID:CID_16745513; ChEMBL:CHEMBL1380003
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(3S,3aalpha,6aalpha)-3alpha,6alpha-Bis(1,3-benzodioxole-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 370.36
Log P RDKit 2.54
Topological polar surface area (Å2) RDKit 75.61
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
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 12
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
(3S,3aalpha,6aalpha)-3alpha,6alpha-Bis(1,3-benzodioxole-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-ol
Drug-likeness
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.870588
(3S,3aalpha,6aalpha)-3alpha,6alpha-Bis(1,3-benzodioxole-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-ol
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 -7.03
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
(3S,3aalpha,6aalpha)-3alpha,6alpha-Bis(1,3-benzodioxole-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-ol
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL