IMPPAT Phytochemical information: 
(1R,7S,9R,10S,13S,15S)-15-hydroxy-7-[(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4,5-disulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5,5-dicarboxylic acid
(1R,7S,9R,10S,13S,15S)-15-hydroxy-7-[(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4,5-disulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5,5-dicarboxylic acid
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2CC(C(=O)O)(C(=O)O)C3[C@@](C2)(C)[C@@H]2CC[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
InChI: InChI=1S/C31H46O18S2/c1-14(2)9-21(33)47-24-23(49-51(42,43)44)22(48-50(39,40)41)18(13-32)46-26(24)45-17-11-29(4)19-6-5-16-10-30(19,25(34)15(16)3)8-7-20(29)31(12-17,27(35)36)28(37)38/h14,16-20,22-26,32,34H,3,5-13H2,1-2,4H3,(H,35,36)(H,37,38)(H,39,40,41)(H,42,43,44)/t16-,17-,18+,19-,20?,22+,23-,24+,25-,26+,29+,30+/m0/s1
InChIKey: AQFATIOBERWBDY-SRIINCLRSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]CCC=O)O))C=O)O))C[C@@]C6)C)[C@@H]CC[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
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
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Norkaurane diterpenoids
Synonymous chemical names:
carboxyatractyloside
External chemical identifiers:
CID:CID_102004836
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,7S,9R,10S,13S,15S)-15-hydroxy-7-[(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4,5-disulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5,5-dicarboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 770.83
Log P RDKit 1.12
Topological polar surface area (Å2) RDKit 287.02
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 51
Number of heteroatoms RDKit 20
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.84
Number of rotatable bonds RDKit 13
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
(1R,7S,9R,10S,13S,15S)-15-hydroxy-7-[(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4,5-disulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5,5-dicarboxylic acid
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 3
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 0.0532795
(1R,7S,9R,10S,13S,15S)-15-hydroxy-7-[(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4,5-disulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5,5-dicarboxylic acid
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 -10.47
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