IMPPAT Phytochemical information: 
Vincarubine
Vincarubine
Summary

SMILES: COC(=O)C1C2CCC34C1(CCN4C/C/2=C\C)C1=CC(=O)C(=CC1=N3)c1cc2c(cc1OC)N(C1=C(CC3(C4C21CCN4CCC3)CC)C(=O)OC)C
InChI: InChI=1S/C43H50N4O6/c1-7-24-23-47-17-14-42-29-20-33(48)26(19-31(29)44-43(42,47)12-10-25(24)35(42)38(50)53-6)27-18-30-32(21-34(27)51-4)45(3)36-28(37(49)52-5)22-40(8-2)11-9-15-46-16-13-41(30,36)39(40)46/h7,18-21,25,35,39H,8-17,22-23H2,1-6H3/b24-7+
InChIKey: CLSRDWBICGYSOB-HCBMXOAHSA-N
DeepSMILES: COC=O)CCCCCC6CCN5C/C/%10=C\C)))))))C=CC=O)C=CC6=N9)))cccccc6OC))))NC=CCCCC96CCN5CCC9))))))))CC))))C=O)OC)))))C
Scaffold Graph/Node/Bond level: C=C1CN2CCC34CC1CCC23N=C1C=C(c2ccc3c(c2)C25CCN6CCCC(CC=C2N3)C65)C(=O)C=C14
Scaffold Graph/Node level: CC1CN2CCC34CC1CCC23NC1CC(C2CCC3NC5CCC6CCCN7CCC5(C3C2)C67)C(O)CC14
Scaffold Graph level: CC1CC2CCC34CC1CCC23CC1CC(C2CCC3CC5CCC6CCCC7CCC5(C3C2)C67)C(C)CC14
Functional groups: COC(C)=O; cC1=CC2=NC(C)(CC2=CC1=O)N(C)C; C/C=C(/C)C; cOC; cN(C)C(=C(C(=O)OC)C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidospermatan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
vincarubine
External chemical identifiers:
CID:CID_6442103
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vincarubine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 718.9
Log P RDKit 5.37
Topological polar surface area (Å2) RDKit 100.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 43
Number of heavy atoms RDKit 53
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 7
Number of aliphatic rings RDKit 10
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 11
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 11
Vincarubine
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 Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.226082
Vincarubine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.92
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME Yes