IMPPAT Phytochemical information: 
Strictosidine
Strictosidine
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H]([C@H]2C=C)C[C@@H]2NCCc3c2[nH]c2c3cccc2)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19+,20-,22-,23+,24-,26+,27+/m1/s1
InChIKey: XBAMJZTXGWPTRM-NTXHKPOFSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@H][C@H]6C=C)))C[C@@H]NCCcc6[nH]cc5cccc6)))))))))))))))C=O)OC))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC(CC2NCCc3c2[nH]c2ccccc32)CC(OC2CCCCO2)O1
Scaffold Graph/Node level: C1CCC(OC2CC(CC3NCCC4C5CCCCC5NC34)CCO2)OC1
Scaffold Graph level: C1CCC(CC2CCCC(CC3CCCC4C5CCCCC5CC34)C2)CC1
Functional groups: CO; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1; C=CC; CNC; c[nH]c
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: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
isovincoside, strictosidine
External chemical identifiers:
CID:CID_161336; ChEMBL:CHEMBL402211; ChEBI:CHEBI:17559; ZINC:ZINC000029046041; SureChEMBL:SCHEMBL8322946
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Strictosidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 530.57
Log P RDKit 0.39
Topological polar surface area (Å2) RDKit 162.73
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Strictosidine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
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 0.218128
Strictosidine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.11
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
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