IMPPAT Phytochemical information: 
3-ethenyl-4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
3-ethenyl-4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
Summary

SMILES: OCC1OC(OC2OC=C(C(C2C=C)CC2NCCc3c2[nH]c2c3cccc2)C(=O)O)C(C(C1O)O)O
InChI: InChI=1S/C26H32N2O9/c1-2-12-15(9-18-20-14(7-8-27-18)13-5-3-4-6-17(13)28-20)16(24(33)34)11-35-25(12)37-26-23(32)22(31)21(30)19(10-29)36-26/h2-6,11-12,15,18-19,21-23,25-32H,1,7-10H2,(H,33,34)
InChIKey: CMMIVMFGFIBAGC-UHFFFAOYSA-N
DeepSMILES: OCCOCOCOC=CCC6C=C)))CCNCCcc6[nH]cc5cccc6)))))))))))))))C=O)O)))))))CCC6O))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(OC1CCC(C(=O)O)=CO1)C; 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:
strictosidinic acid
External chemical identifiers:
CID:CID_73806906
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-ethenyl-4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 516.55
Log P RDKit 0.3
Topological polar surface area (Å2) RDKit 173.73
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 37
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 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 7
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
3-ethenyl-4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
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 0.25
3-ethenyl-4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.88
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 No