IMPPAT Phytochemical information: 
1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-6-hydroxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-6-hydroxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
Summary

SMILES: C=C[C@H]1[C@@H](OC=C([C@H]1Cc1nc(cc2c1[nH]c1c2cc(cc1)O)C(=O)O)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C28H30N2O12/c1-3-12-13(7-18-21-15(8-19(29-18)25(36)37)14-6-11(32)4-5-17(14)30-21)16(26(38)39-2)10-40-27(12)42-28-24(35)23(34)22(33)20(9-31)41-28/h3-6,8,10,12-13,20,22-24,27-28,30-35H,1,7,9H2,2H3,(H,36,37)/t12-,13+,20-,22-,23+,24-,27+,28+/m1/s1
InChIKey: HFPKTEZZZRPDQU-FAEAJWQNSA-N
DeepSMILES: C=C[C@H][C@@H]OC=C[C@H]6Ccncccc6[nH]cc5cccc6))O)))))))))C=O)O)))))))C=O)OC))))))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC(Cc2nccc3c2[nH]c2ccccc23)CC(OC2CCCCO2)O1
Scaffold Graph/Node level: C1CCC(OC2CC(CC3NCCC4C5CCCCC5NC34)CCO2)OC1
Scaffold Graph level: C1CCC(CC2CCCC(CC3CCCC4C5CCCCC5CC34)C2)CC1
Functional groups: C=CC; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1; cnc; c[nH]c; cO; cC(=O)O; CO
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:
cordifoline
External chemical identifiers:
CID:CID_21593932; ZINC:ZINC000044351601
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-6-hydroxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 586.55
Log P RDKit 0.31
Topological polar surface area (Å2) RDKit 221.12
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.39
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
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
1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-6-hydroxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
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 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 0.139679
1-[[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-6-hydroxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -9.28
Number of PAINS structural alerts SwissADME 0
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