IMPPAT Phytochemical information: 
Daturataturin A
Daturataturin A
Summary

SMILES: OC[C@H]1O[C@@H](OCC2=C(C)C[C@@H](OC2=O)[C@H]([C@H]2CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3[C@H](O)C=C3[C@]2(C)C(=O)C=CC3)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C34H48O10/c1-16-12-24(43-31(41)19(16)15-42-32-30(40)29(39)28(38)25(14-35)44-32)17(2)20-8-9-21-27-22(10-11-33(20,21)3)34(4)18(13-23(27)36)6-5-7-26(34)37/h5,7,13,17,20-25,27-30,32,35-36,38-40H,6,8-12,14-15H2,1-4H3/t17-,20+,21-,22-,23+,24+,25+,27-,28+,29-,30+,32+,33+,34-/m0/s1
InChIKey: FYXDMSFPWCORTF-UWOSJZGMSA-N
DeepSMILES: OC[C@H]O[C@@H]OCC=CC)C[C@@H]OC6=O)))[C@H][C@H]CC[C@@H][C@]5C)CC[C@H][C@H]6[C@H]O)C=C[C@]6C)C=O)C=CC6)))))))))))))))))C))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OC(CC2CCC3C2CCC2C4C(=O)C=CCC4=CCC23)CC=C1COC1CCCCO1
Scaffold Graph/Node level: OC1CCCC2CCC3C4CCC(CC5CCC(COC6CCCCO6)C(O)O5)C4CCC3C12
Scaffold Graph level: CC1CC(CC2CCC3C2CCC2C3CCC3CCCC(C)C32)CCC1CCC1CCCCC1
Functional groups: CO; CO[C@@H](C)OC; CC1=C(C)C(=O)OCC1; CC(=CC)C; CC=CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ergostane steroids
Synonymous chemical names:
(22r)-7α,27-dihydroxy-1-oxo-with a-2,5,24-trienolide-27-o-β-d-glucopyranoside (daturataturin a), Daturataturin A, daturataturin a
External chemical identifiers:
CID:CID_14825627; ZINC:ZINC000252585089; MolPort-035-706-544
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Daturataturin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 616.75
Log P RDKit 1.97
Topological polar surface area (Å2) RDKit 162.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Daturataturin A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
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 0.22
Daturataturin A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -8.39
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 Yes