IMPPAT Phytochemical information: 
Thapsuine A
Thapsuine A
Summary

SMILES: OCC1OC(OC2C(C)OC(C(C2O)O)OCC2OC(O[C@H]3CC[C@]4([C@H]([C@]3(C)CO)CC[C@@]3([C@@H]4C=C[C@]45[C@@]3(C)CC[C@@]3([C@H]5CC(C)(C)CC3)CO4)C)C)C(C(C2O)OC2OC(C)C(C(C2O)O)O)O)C(C(C1O)O)O
InChI: InChI=1S/C54H88O21/c1-24-32(57)35(60)38(63)45(69-24)75-43-34(59)27(21-67-44-40(65)37(62)42(25(2)70-44)74-46-39(64)36(61)33(58)26(20-55)71-46)72-47(41(43)66)73-31-11-12-49(5)28(50(31,6)22-56)9-13-51(7)29(49)10-14-54-30-19-48(3,4)15-17-53(30,23-68-54)18-16-52(51,54)8/h10,14,24-47,55-66H,9,11-13,15-23H2,1-8H3/t24?,25?,26?,27?,28-,29-,30-,31+,32?,33?,34?,35?,36?,37?,38?,39?,40?,41?,42?,43?,44?,45?,46?,47?,49+,50+,51-,52+,53-,54+/m1/s1
InChIKey: AGRBCEPQHVINNI-XQGZWKFBSA-N
DeepSMILES: OCCOCOCCC)OCCC6O))O))OCCOCO[C@H]CC[C@][C@H][C@]6C)CO)))CC[C@@][C@@H]6C=C[C@@][C@@]6C)CC[C@@][C@H]6CCC)C)CC6)))))CO7))))))))))C)))))C))))))CCC6O))OCOCC)CCC6O))O))O)))))))O))))))))))))CCC6O))O))O
Scaffold Graph/Node/Bond level: C1=CC23OCC4(CCCCC42)CCC3C2CCC3CC(OC4CC(OC5CCCCO5)CC(COC5CCC(OC6CCCCO6)CO5)O4)CCC3C12
Scaffold Graph/Node level: C1CCC(OC2CCC(OCC3CC(OC4CCCCO4)CC(OC4CCC5C(CCC6C5CCC57OCC8(CCCCC85)CCC67)C4)O3)OC2)OC1
Scaffold Graph level: C1CCC(CC2CCC(CCC3CC(CC4CCCCC4)CC(CC4CCC5C(CCC6C5CCC57CCC8(CCCCC85)CCC67)C4)C3)CC2)CC1
Functional groups: CC=CC; CO; COC; COC(C)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: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
thapsuine a, thapsuines a
External chemical identifiers:
CID:5458837
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Thapsuine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1073.28
Log P RDKit -0.52
Topological polar surface area (Å2) RDKit 325.83
Number of hydrogen bond acceptors RDKit 21
Number of hydrogen bond donors RDKit 12
Number of carbon atoms RDKit 54
Number of heavy atoms RDKit 75
Number of heteroatoms RDKit 21
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 30
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 52
Shape complexity RDKit 0.96
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 10
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 9
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
Thapsuine 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 4
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 0.0915
Thapsuine A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -12.67
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes