IMPPAT Phytochemical information: 
Acaciaside B

Acaciaside B
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@](CC/C=C(/C(=O)O[C@H]2C[C@]3(C(=O)O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@@H]([C@H]([C@H]5O)O)O)[C@H]([C@@H]([C@H]4O[C@@H]4OC[C@H]([C@@H]([C@H]4O)O)O)O)O)[C@@H](O)C[C@@]4(C(=CC[C@H]5[C@@]4(C)CC[C@@H]4[C@]5(C)CC[C@@H](C4(C)C)O[C@@H]4O[C@H](CO[C@@H]5O[C@H](CO)[C@H]([C@@H]([C@H]5O)O)O)[C@H]([C@@H]([C@H]4O[C@@H]4OC[C@@H]([C@@H]([C@H]4O)O)O)O)O)[C@@H]3CC2(C)C)C)C)(C=C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C85H136O43/c1-12-81(8,128-77-68(58(102)53(97)40(26-87)119-77)126-74-63(107)51(95)38(90)29-114-74)19-13-14-32(2)69(110)122-47-24-85(78(111)127-76-67(125-73-62(106)50(94)37(89)28-113-73)60(104)55(99)42(121-76)30-115-70-64(108)56(100)48(92)33(3)117-70)35(22-79(47,4)5)34-15-16-44-82(9)20-18-46(80(6,7)43(82)17-21-83(44,10)84(34,11)23-45(85)91)123-75-66(124-72-61(105)49(93)36(88)27-112-72)59(103)54(98)41(120-75)31-116-71-65(109)57(101)52(96)39(25-86)118-71/h12,14-15,33,35-68,70-77,86-109H,1,13,16-31H2,2-11H3/b32-14+/t33-,35-,36-,37+,38+,39+,40+,41+,42+,43-,44+,45-,46-,47-,48-,49-,50-,51-,52+,53+,54+,55+,56+,57-,58-,59-,60-,61+,62+,63+,64+,65+,66+,67+,68+,70+,71+,72-,73-,74-,75-,76-,77-,81+,82-,83+,84+,85+/m0/s1
InChIKey: JDBRROFHWPVSFD-OWMANMSFSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@]CC/C=C/C=O)O[C@H]C[C@]C=O)O[C@@H]O[C@H]CO[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O)))))))[C@H][C@@H][C@H]6O[C@@H]OC[C@H][C@@H][C@H]6O))O))O)))))))O))O)))))))[C@@H]O)C[C@@]C=CC[C@H][C@@]6C)CC[C@@H][C@]6C)CC[C@@H]C6C)C))O[C@@H]O[C@H]CO[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))[C@H][C@@H][C@H]6O[C@@H]OC[C@@H][C@@H][C@H]6O))O))O)))))))O))O)))))))))))))))))[C@@H]6CC%10C)C)))))C)))))))))C)))))C=C))C)))[C@@H][C@H][C@@H]6O))O))O[C@@H]OC[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=CCCCOC1OCCCC1OC1CCCCO1)OC1CCC2C3=CCC4C5CCC(OC6OC(COC7CCCCO7)CCC6OC6CCCCO6)CC5CCC4C3CCC2(C(=O)OC2OC(COC3CCCCO3)CCC2OC2CCCCO2)C1
Scaffold Graph/Node level: OC(CCCCCOC1OCCCC1OC1CCCCO1)OC1CCC2C3CCC4C5CCC(OC6OC(COC7CCCCO7)CCC6OC6CCCCO6)CC5CCC4C3CCC2(C(O)OC2OC(COC3CCCCO3)CCC2OC2CCCCO2)C1
Scaffold Graph level: CC(CCCCCCC1CCCCC1CC1CCCCC1)CC1CCC2C3CCC4C5CCC(CC6CC(CCC7CCCCC7)CCC6CC6CCCCC6)CC5CCC4C3CCC2(C(C)CC2CC(CCC3CCCCC3)CCC2CC2CCCCC2)C1
Functional groups: C/C=C(C)C(=O)OC; C=CC; CC=C(C)C; CO; CO[C@@H](C)OC; CO[C@H](C)OC; CO[C@H](C)OC(C)=O
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:
acaciaside b
External chemical identifiers:
CID:102094667
Chemical structure download


Acaciaside B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1845.98
Log P RDKit -7.64
Topological polar surface area (Å2) RDKit 676.57
Number of hydrogen bond acceptors RDKit 43
Number of hydrogen bond donors RDKit 24
Number of carbon atoms RDKit 85
Number of heavy atoms RDKit 128
Number of heteroatoms RDKit 43
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 48
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 77
Shape complexity RDKit 0.91
Number of rotatable bonds RDKit 28
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 8
Number of aliphatic rings RDKit 13
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 13
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 8
Number of saturated rings RDKit 12
Number of Smallest Set of Smallest Rings (SSSR) RDKit 13


Acaciaside B
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 0.0166