IMPPAT Phytochemical information: 
methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10,11-dihydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10,11-dihydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
Summary

SMILES: COc1cc2N(C=O)[C@@H]3[C@@]4(c2cc1[C@]1(CC2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)O)(CC)C=CC1
InChI: InChI=1S/C44H54N4O9/c1-6-40(53)21-26-22-43(38(51)56-4,34-28(13-17-46(23-26)24-40)27-11-8-9-12-31(27)45-34)30-19-29-32(20-33(30)55-3)48(25-49)36-42(29)15-18-47-16-10-14-41(7-2,35(42)47)37(50)44(36,54)39(52)57-5/h8-12,14,19-20,25-26,35-37,45,50,53-54H,6-7,13,15-18,21-24H2,1-5H3/t26?,35-,36+,37+,40-,41+,42+,43-,44-/m0/s1
InChIKey: YIQATJBOCJPFCF-KPKUDKDBSA-N
DeepSMILES: COcccNC=O))[C@@H][C@@]c5cc9[C@]CCCNCCcc9[nH]cc5cccc6)))))))))))C[C@]C6)O)CC))))))))C=O)OC)))))))CCN[C@H]5[C@@][C@H][C@]9O)C=O)OC))))O))CC))C=CC6
Scaffold Graph/Node/Bond level: C1=CC2CCC3Nc4ccc(C5CC6CCCN(CCc7c5[nH]c5ccccc75)C6)cc4C34CCN(C1)C24
Scaffold Graph/Node level: C1CCC2C(C1)NC1C(C3CCC4NC5CCC6CCCN7CCC5(C4C3)C67)CC3CCCN(CCC21)C3
Scaffold Graph level: C1CC2CCC3C4CCCCC4CC3C(C3CCC4CC5CCC6CCCC7CCC5(C4C3)C67)CC(C1)C2
Functional groups: CO; cOC; COC(C)=O; cN(C=O)C; CN(C)C; CC=CC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Vinca alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type|Aspidosperma-Iboga hybrid type (Vinca alkaloids)
Synonymous chemical names:
4-deacetylvincristine
External chemical identifiers:
CID:CID_59706266; SureChEMBL:SCHEMBL14177989
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10,11-dihydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 782.94
Log P RDKit 2.95
Topological polar surface area (Å2) RDKit 165.1
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 57
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10,11-dihydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-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 3
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 0.16
methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10,11-dihydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes