IMPPAT Phytochemical information: 
(6aS,11bS)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol
(6aS,11bS)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol
Summary

SMILES: Oc1ccc2c(c1)OC[C@]1([C@H]2c2cc(O)c(cc2C1)O)O
InChI: InChI=1S/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16-/m1/s1
InChIKey: UWHUTZOCTZJUKC-HZPDHXFCSA-N
DeepSMILES: Occcccc6)OC[C@][C@H]6cccO)ccc6C9)))O))))))O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1COc3ccccc3C21
Scaffold Graph/Node level: C1CCC2C(C1)CC1COC3CCCCC3C12
Scaffold Graph level: C1CCC2C(C1)CCC1CC3CCCCC3C12
Functional groups: cO; cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
Synonymous chemical names:
brasilin, brazilin
External chemical identifiers:
CID:CID_36689482; ZINC:ZINC000001648165
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(6aS,11bS)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 286.28
Log P RDKit 1.61
Topological polar surface area (Å2) RDKit 90.15
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
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 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
(6aS,11bS)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.552475
(6aS,11bS)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol
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 -6.95
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes