IMPPAT Phytochemical information: 
(2S,3R,4S,4aR,6aR,6bR,8aS,12aR,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-d
(2S,3R,4S,4aR,6aR,6bR,8aS,12aR,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-d
Summary

SMILES: COc1ccc(cc1)/C=C/C(=O)O[C@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)OC(=O)[C@@]12CCC(C[C@@H]2C2=CC[C@H]3[C@@]([C@@]2(CC1)CO)(C)CC[C@@H]1[C@]3(C)C[C@@H]([C@@H]([C@@]1(C)C(=O)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)(C)C
InChI: InChI=1S/C75H112O35/c1-30-44(80)48(84)53(89)63(99-30)108-59-58(106-43(79)17-12-33-10-13-34(97-9)14-11-33)32(3)101-67(60(59)109-64-56(92)51(87)57(31(2)100-64)107-62-52(88)47(83)40(28-98-62)105-66-55(91)50(86)46(82)39(27-77)104-66)110-69(96)74-21-20-70(4,5)24-36(74)35-15-16-41-71(6)25-37(102-65-54(90)49(85)45(81)38(26-76)103-65)61(93)73(8,68(94)95)42(71)18-19-72(41,7)75(35,29-78)23-22-74/h10-15,17,30-32,36-42,44-67,76-78,80-93H,16,18-29H2,1-9H3,(H,94,95)/b17-12+/t30-,31-,32+,36+,37-,38+,39+,40-,41+,42+,44-,45+,46-,47-,48+,49-,50-,51-,52+,53+,54+,55+,56+,57-,58-,59-,60+,61-,62-,63-,64-,65+,66-,67-,71+,72+,73-,74-,75-/m0/s1
InChIKey: FXJGOVMMSNBPON-UBYURVNVSA-N
DeepSMILES: COcccccc6))/C=C/C=O)O[C@H][C@@H]C)O[C@H][C@@H][C@H]6O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O)))))))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O[C@@H]OC[C@@H][C@@H][C@H]6O))O))O[C@@H]O[C@H]CO))[C@@H][C@@H][C@H]6O))O))O)))))))))))))))))OC=O)[C@]CCCC[C@@H]6C=CC[C@H][C@@][C@@]6CC%14))CO)))C)CC[C@@H][C@]6C)C[C@@H][C@@H][C@@]6C)C=O)O)))O))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))))))))))))))C)C
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1COC(OC(=O)C23CCCCC2C2=CCC4C5CC(OC6CCCCO6)CCC5CCC4C2CC3)C(OC2CCC(OC3CCC(OC4CCCCO4)CO3)CO2)C1OC1CCCCO1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1COC(OC(O)C23CCCCC2C2CCC4C5CC(OC6CCCCO6)CCC5CCC4C2CC3)C(OC2CCC(OC3CCC(OC4CCCCO4)CO3)CO2)C1OC1CCCCO1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC(CC(C)C23CCCCC2C2CCC4C5CC(CC6CCCCC6)CCC5CCC4C2CC3)C(CC2CCC(CC3CCC(CC4CCCCC4)CC3)CC2)C1CC1CCCCC1
Functional groups: CC(=O)O; CC(=O)O[C@@H](C)OC; CC=C(C)C; CO; CO[C@@H](C)OC; CO[C@H](C)OC; c/C=C/C(=O)OC; cOC
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:
senegin iiis
External chemical identifiers:
CID:44566675; ChEMBL:CHEMBL506899
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3R,4S,4aR,6aR,6bR,8aS,12aR,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-d
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1573.69
Log P RDKit -3.38
Topological polar surface area (Å2) RDKit 544.57
Number of hydrogen bond acceptors RDKit 34
Number of hydrogen bond donors RDKit 18
Number of carbon atoms RDKit 75
Number of heavy atoms RDKit 110
Number of heteroatoms RDKit 35
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 39
Stereochemical complexity RDKit 0.52
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 62
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 22
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 11
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 12
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 6
Number of saturated rings RDKit 10
Number of Smallest Set of Smallest Rings (SSSR) RDKit 12
(2S,3R,4S,4aR,6aR,6bR,8aS,12aR,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-d
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 0.0262