IMPPAT Phytochemical information: 
(2S)-8-[5-[(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran)-2alpha-yl]-2-hydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-2alpha-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
(2S)-8-[5-[(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran)-2alpha-yl]-2-hydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-2alpha-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Summary

SMILES: Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)c(c(cc2O)O)c1cc(ccc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
InChI: InChI=1S/C30H22O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-10,24-25,31-36H,11-12H2/t24-,25-/m0/s1
InChIKey: ULTQJSQDLWNWTR-DQEYMECFSA-N
DeepSMILES: Occcccc6))[C@@H]CC=O)ccO6)cccc6O)))O))cccccc6O))))[C@@H]CC=O)ccO6)cccc6O)))O
Scaffold Graph/Node/Bond level: O=C1CC(c2cccc(-c3cccc4c3OC(c3ccccc3)CC4=O)c2)Oc2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCCC(C3CCCC4C(O)CC(C5CCCCC5)OC43)C2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC(C3CCCC4C(C)CC(C5CCCCC5)CC43)C2)CC2CCCCC12
Functional groups: cO; cOC; cC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Biflavonoids and polyflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
tetrahydroamentoflavone
External chemical identifiers:
CID:CID_91884783; ChEMBL:CHEMBL4287858; ZINC:ZINC000005493456; MolPort-039-052-619
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S)-8-[5-[(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran)-2alpha-yl]-2-hydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-2alpha-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 542.5
Log P RDKit 5
Topological polar surface area (Å2) RDKit 173.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 26
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.13
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6
(2S)-8-[5-[(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran)-2alpha-yl]-2-hydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-2alpha-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.206688
(2S)-8-[5-[(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran)-2alpha-yl]-2-hydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-2alpha-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.42
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
(2S)-8-[5-[(3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran)-2alpha-yl]-2-hydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-2alpha-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
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_001779ENSG00000147162OGT8473ChEMBL