IMPPAT | IMPPAT: Indian Medicinal Plants, Phytochemistry And Therapeutics

(2R,3R,4S,5S,6R)-2-[(2S)-2-[(1R,2S,2'S,4aR,4bR,6aR,7R,8S,10aR,10bR,12aS)-8-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1-hydroxy-7-(hydroxymethyl)-4a,4b,7,10a-tetramethylspiro[3,4,5,6,6a,8,9,10,10b,11,12,12a-dodecahydro-1H-chrysene-2,5'-oxane]-2'-yl]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC[C@H]3[C@@]2(C)CC[C@]2([C@@H]3O)CC[C@H](OC2)[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C48H82O20/c1-22(19-62-41-37(59)34(56)31(53)25(16-49)64-41)24-8-13-48(21-63-24)15-14-46(4)23(40(48)61)6-7-29-44(2)11-10-30(45(3,20-52)28(44)9-12-47(29,46)5)67-43-39(36(58)33(55)27(18-51)66-43)68-42-38(60)35(57)32(54)26(17-50)65-42/h22-43,49-61H,6-21H2,1-5H3/t22-,23+,24-,25+,26+,27+,28+,29+,30-,31+,32+,33+,34-,35-,36-,37+,38+,39+,40+,41+,42-,43-,44-,45-,46+,47+,48+/m0/s1
InChIKey: GBXXXUUAOFPGRP-MDQYKXRHSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]CC[C@][C@H][C@]6C)CO)))CC[C@@][C@@H]6CC[C@H][C@@]6C)CC[C@][C@@H]6O))CC[C@H]OC6))[C@H]CO[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))C)))))))))))))C)))))C))))))[C@@H][C@H][C@@H]6O))O))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCC(OCCC2CCC3(CCC4C(CCC5C6CCC(OC7OCCCC7OC7CCCCO7)CC6CCC45)C3)CO2)OC1
Scaffold Graph/Node level: C1CCC(OCCC2CCC3(CCC4C(CCC5C6CCC(OC7OCCCC7OC7CCCCO7)CC6CCC45)C3)CO2)OC1
Scaffold Graph level: C1CCC(CCCC2CCC3(CC2)CCC2C(CCC4C5CCC(CC6CCCCC6CC6CCCCC6)CC5CCC24)C3)CC1
Functional groups: CO; CO[C@@H](C)OC; COC

Chemical classification

ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids

Synonymous chemical names:
hosenkoside b

External chemical identifiers:
CID:CID_102004581 ; ZINC:ZINC000390835428 ; MolPort-039-338-324

Chemical structure download

2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT

Physicochemical properties

Property name	Tool	Property value
Molecular weight (g/mol)	RDKit	979.16
Log P	RDKit	-1.98
Topological polar surface area (Å²)	RDKit	327.6
Number of hydrogen bond acceptors	RDKit	20
Number of hydrogen bond donors	RDKit	13
Number of carbon atoms	RDKit	48
Number of heavy atoms	RDKit	68
Number of heteroatoms	RDKit	20
Number of nitrogen atoms	RDKit	0
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	27
Stereochemical complexity	RDKit	0.56
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	0
Number of sp³ hybridized carbon atoms	RDKit	48
Shape complexity	RDKit	1
Number of rotatable bonds	RDKit	12
Number of aliphatic carbocycles	RDKit	4
Number of aliphatic heterocycles	RDKit	4
Number of aliphatic rings	RDKit	8
Number of aromatic carbocycles	RDKit	0
Number of aromatic heterocycles	RDKit	0
Number of aromatic rings	RDKit	0
Total number of rings	RDKit	8
Number of saturated carbocycles	RDKit	4
Number of saturated heterocycles	RDKit	4
Number of saturated rings	RDKit	8
Number of Smallest Set of Smallest Rings (SSSR)	RDKit	8

Drug-likeness properties

Property name	Tool	Property value
Number of Lipinski’s rule of 5 violations	RDKit	3
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	0.09