IMPPAT Phytochemical information: 
Curculigine A
Curculigine A
Summary

SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc(OC)c(c(c3Cl)C)Cl)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H28Cl2O12/c1-6-11(21)7(30-2)3-8(12(6)22)32-20-18(29)16(27)14(25)10(34-20)5-31-19-17(28)15(26)13(24)9(4-23)33-19/h3,9-10,13-20,23-29H,4-5H2,1-2H3/t9-,10-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
InChIKey: XBVNHJLYWKRWAX-RPDXMDMVSA-N
DeepSMILES: OC[C@H]O[C@@H]OC[C@H]O[C@@H]OcccOC))ccc6Cl))C))Cl))))))[C@@H][C@H][C@@H]6O))O))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(OC2CCCC(COC3CCCCO3)O2)cc1
Scaffold Graph/Node level: C1CCC(OC2CCCC(COC3CCCCO3)O2)CC1
Scaffold Graph level: C1CCC(CCC2CCCC(CC3CCCCC3)C2)CC1
Functional groups: CO; CO[C@@H](C)OC; cO[C@@H](C)OC; cOC; cCl
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Polyketides
Synonymous chemical names:
curculigine a
External chemical identifiers:
CID:CID_183146
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Curculigine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 531.34
Log P RDKit -1.69
Topological polar surface area (Å2) RDKit 187.76
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 7
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 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
Curculigine A
Drug-likeness properties
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.212032
Curculigine A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -10.10
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No