IMPPAT Phytochemical information: 
methyl (1S,15S,16S,17S,21S)-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,23-dioxa-3,13-diazahexacyclo[13.7.1.01,13.02,10.04,9.016,21]tricosa-2(10),4,6,8,19-pentaene-20-carboxylate
methyl (1S,15S,16S,17S,21S)-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,23-dioxa-3,13-diazahexacyclo[13.7.1.01,13.02,10.04,9.016,21]tricosa-2(10),4,6,8,19-pentaene-20-carboxylate
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@H]2CN4[C@](O2)(C3)c2[nH]c3c(c2CC4)cccc3)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H32N2O10/c1-35-24(34)15-11-36-25(38-26-22(33)21(32)20(31)18(10-30)37-26)19-14(15)8-27-23-13(6-7-29(27)9-17(19)39-27)12-4-2-3-5-16(12)28-23/h2-5,11,14,17-22,25-26,28,30-33H,6-10H2,1H3/t14-,17-,18-,19+,20-,21+,22-,25+,26+,27+/m1/s1
InChIKey: OVRROYYXOBYCSR-QUXSSVLGSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@H]CN[C@]O5)C7)c[nH]ccc5CC9)))cccc6))))))))))))))C=O)OC))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC2CC34OC(CN3CCc3c4[nH]c4ccccc34)C2C(OC2CCCCO2)O1
Scaffold Graph/Node level: C1CCC(OC2OCCC3CC45OC(CN4CCC4C6CCCCC6NC45)C32)OC1
Scaffold Graph level: C1CCC(CC2CCCC3CC45CC(CC4CCC4C6CCCCC6CC45)C23)CC1
Functional groups: CO; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1; c[C@]1(C)OCCN1C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
cadambine
External chemical identifiers:
CID:CID_21723831; ZINC:ZINC000143329710
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1S,15S,16S,17S,21S)-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,23-dioxa-3,13-diazahexacyclo[13.7.1.01,13.02,10.04,9.016,21]tricosa-2(10),4,6,8,19-pentaene-20-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 544.56
Log P RDKit -0.56
Topological polar surface area (Å2) RDKit 163.17
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.59
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
methyl (1S,15S,16S,17S,21S)-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,23-dioxa-3,13-diazahexacyclo[13.7.1.01,13.02,10.04,9.016,21]tricosa-2(10),4,6,8,19-pentaene-20-carboxylate
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 4
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 0.31
methyl (1S,15S,16S,17S,21S)-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,23-dioxa-3,13-diazahexacyclo[13.7.1.01,13.02,10.04,9.016,21]tricosa-2(10),4,6,8,19-pentaene-20-carboxylate
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 -9.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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