IMPPAT Phytochemical information: 
Ammijin
Ammijin
Summary

SMILES: OC[C@H]1O[C@@H](OC([C@H]2Oc3c(C2)cc2c(c3)oc(=O)cc2)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H24O9/c1-20(2,29-19-18(25)17(24)16(23)13(8-21)28-19)14-6-10-5-9-3-4-15(22)27-11(9)7-12(10)26-14/h3-5,7,13-14,16-19,21,23-25H,6,8H2,1-2H3/t13-,14+,16-,17+,18-,19+/m1/s1
InChIKey: HXCGUCZXPFBNRD-NEDVQNLSSA-N
DeepSMILES: OC[C@H]O[C@@H]OC[C@H]OccC5)cccc6)oc=O)cc6)))))))))))C)C)))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccc2cc3c(cc2o1)OC(COC1CCCCO1)C3
Scaffold Graph/Node level: OC1CCC2CC3CC(COC4CCCCO4)OC3CC2O1
Scaffold Graph level: CC1CCC2CC3CC(CCC4CCCCC4)CC3CC2C1
Functional groups: CO; CO[C@@H](C)OC; cOC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Furanocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins
Synonymous chemical names:
marmesinin, 2'-beta-d-glucopyranosyloxy-marmesine, ammajin, Marmesinin
External chemical identifiers:
CID:CID_216283; ChEBI:CHEBI:132401; ZINC:ZINC000031597169; FDASRS:1C1VEU88IF; MolPort-039-338-572
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ammijin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 408.4
Log P RDKit -0.31
Topological polar surface area (Å2) RDKit 138.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Ammijin
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 Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.5
Ammijin
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.56
Number of PAINS structural alerts SwissADME 0
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 No