IMPPAT Phytochemical information: 
Holothurin A
Holothurin A
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2[C@@H](C)O[C@H]([C@@H]([C@H]2O)O)O[C@H]2[C@@H](OC[C@H]([C@@H]2O)OS(=O)(=O)[O-])O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@H]2C3=C[C@H](O)[C@]34[C@@]2(C)CC[C@]4(O)[C@](OC3=O)(C)[C@@H]2CCC(O2)(C)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)OC)O)O.[Na+]
InChI: InChI=1S/C54H86O27S.Na/c1-22-39(76-45-38(64)41(33(59)26(20-56)74-45)77-44-37(63)40(70-9)32(58)25(19-55)73-44)35(61)36(62)43(72-22)78-42-34(60)27(81-82(67,68)69)21-71-46(42)75-30-13-15-50(6)24-18-29(57)54-47(65)80-52(8,31-12-14-48(2,3)79-31)53(54,66)17-16-51(54,7)23(24)10-11-28(50)49(30,4)5;/h18,22-23,25-46,55-64,66H,10-17,19-21H2,1-9H3,(H,67,68,69);/q;+1/p-1/t22-,23-,25-,26-,27-,28+,29+,30+,31+,32-,33-,34+,35-,36-,37-,38-,39-,40+,41+,42-,43+,44+,45+,46+,50-,51+,52+,53+,54-;/m1./s1
InChIKey: KXDQPKMJSMCBEY-VOFJYVFSSA-M
DeepSMILES: OC[C@H]O[C@@H]O[C@@H][C@@H]C)O[C@H][C@@H][C@H]6O))O))O[C@H][C@@H]OC[C@H][C@@H]6O))OS=O)=O)[O-]))))))O[C@H]CC[C@][C@H]C6C)C))CC[C@@H]C6=C[C@H]O)[C@@][C@@]6C)CC[C@]5O)[C@]OC8=O)))C)[C@@H]CCCO5)C)C))))))))))))))))))C))))))))))))))[C@@H][C@H][C@@H]6O))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))OC)))O)))))))O.[Na+]
Scaffold Graph/Node/Bond level: O=C1OC(C2CCCO2)C2CCC3C4CCC5CC(OC6OCCCC6OC6CCC(OC7CC(OC8CCCCO8)CCO7)CO6)CCC5C4=CCC132
Scaffold Graph/Node level: OC1OC(C2CCCO2)C2CCC3C4CCC5CC(OC6OCCCC6OC6CCC(OC7CC(OC8CCCCO8)CCO7)CO6)CCC5C4CCC132
Scaffold Graph level: CC1CC(C2CCCC2)C2CCC3C4CCC5CC(CC6CCCCC6CC6CCC(CC7CCCC(CC8CCCCC8)C7)CC6)CCC5C4CCC123
Functional groups: CC=C(C)C; CO; COC; COC(C)=O; COS(=O)(=O)[O-]; CO[C@@H](C)OC; CO[C@H](C)OC; [Na+]
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: Lanostane, Tirucallane and Euphane triterpenoids
Synonymous chemical names:
11-keto-boswellic acid
External chemical identifiers:
CID:23675050; FDASRS:1EV65QT62C; SureChEMBL:SCHEMBL241238
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Holothurin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1221.3
Log P RDKit -5.6
Topological polar surface area (Å2) RDKit 407.56
Number of hydrogen bond acceptors RDKit 27
Number of hydrogen bond donors RDKit 11
Number of carbon atoms RDKit 54
Number of heavy atoms RDKit 83
Number of heteroatoms RDKit 29
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 29
Stereochemical complexity RDKit 0.54
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 51
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 14
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 6
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 3
Number of saturated heterocycles RDKit 6
Number of saturated rings RDKit 9
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
Holothurin 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 0.0193