IMPPAT Phytochemical information: 
Ambap17754-44-8
Ambap17754-44-8
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2C[C@@H](C(=O)O)C3[C@](C2)(C)C2CC[C@@H]4C[C@@]2(CC3)[C@@H](O)C4=C)[C@@H]([C@H]([C@@H]1OS(=O)(=O)[O-])OS(=O)(=O)[O-])OC(=O)CC(C)C.[K+].[K+]
InChI: InChI=1S/C30H46O16S2.2K/c1-14(2)9-22(32)44-25-24(46-48(39,40)41)23(45-47(36,37)38)20(13-31)43-28(25)42-17-10-18(27(34)35)19-7-8-30-11-16(15(3)26(30)33)5-6-21(30)29(19,4)12-17;;/h14,16-21,23-26,28,31,33H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37,38)(H,39,40,41);;/q;2*+1/p-2/t16-,17-,18-,19?,20-,21?,23-,24+,25-,26+,28-,29-,30-;;/m1../s1
InChIKey: IUCNQFHEWLYECJ-BDQDKTDDSA-L
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]C[C@@H]C=O)O))C[C@]C6)C)CCC[C@@H]C[C@@]6CC%10))[C@@H]O)C5=C)))))))))))))))[C@@H][C@H][C@@H]6OS=O)=O)[O-]))))OS=O)=O)[O-]))))OC=O)CCC)C.[K+].[K+]
Scaffold Graph/Node/Bond level: C=C1CC23CCC4CCC(OC5CCCCO5)CC4C2CCC1C3
Scaffold Graph/Node level: CC1CC23CCC4CCC(OC5CCCCO5)CC4C2CCC1C3
Scaffold Graph level: CC1CC23CCC4CCC(CC5CCCCC5)CC4C2CCC1C3
Functional groups: CO; CO[C@@H](C)OC; CC(=O)O; C=C(C)C; COS(=O)(=O)[O-]; CC(=O)OC; [K+]
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
Synonymous chemical names:
atractyloside
External chemical identifiers:
CID:CID_118701294
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ambap17754-44-8
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 803
Log P RDKit -5.01
Topological polar surface area (Å2) RDKit 255.38
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 50
Number of heteroatoms RDKit 20
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 13
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.87
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Ambap17754-44-8
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Bad
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 0.04
Ambap17754-44-8
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.37
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes