IMPPAT Phytochemical information: 
Ephedrannin A
Ephedrannin A
Summary

SMILES: Oc1ccc(cc1)c1oc2c(c(=O)c1O)c(O)cc1c2[C@@H]2c3c(O)cc(cc3O[C@](O1)([C@H]2O)c1ccc(cc1)O)O
InChI: InChI=1S/C30H20O11/c31-14-5-1-12(2-6-14)27-26(37)25(36)22-18(35)11-20-23(28(22)39-27)24-21-17(34)9-16(33)10-19(21)40-30(41-20,29(24)38)13-3-7-15(32)8-4-13/h1-11,24,29,31-35,37-38H/t24-,29-,30+/m0/s1
InChIKey: GPBSBBVDERLESN-QZFRTWIZSA-N
DeepSMILES: Occcccc6))coccc=O)c6O)))cO)ccc6[C@@H]ccO)cccc6O[C@]O%12)[C@H]%10O))cccccc6))O)))))))))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2c3c(ccc12)OC1(c2ccccc2)CC3c2ccccc2O1
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2C1CCC1OC3(C4CCCCC4)CC(C4CCCCC4O3)C12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2C1CCC1CC3(C4CCCCC4)CC4CCCCC4C(C3)C12
Functional groups: cO; CO; coc; c=O; cO[C@](c)(C)Oc
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: Proanthocyanins
Synonymous chemical names:
ephedrannin a
External chemical identifiers:
CID:CID_21676348; ZINC:ZINC000095619715; SureChEMBL:SCHEMBL11130617
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ephedrannin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 556.48
Log P RDKit 3.82
Topological polar surface area (Å2) RDKit 190.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 27
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 2
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 1
Number of aromatic rings RDKit 5
Total number of rings RDKit 7
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 7
Ephedrannin A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.17
Ephedrannin A
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 -6.97
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