IMPPAT Phytochemical information: 
Vincamine

Vincamine
Summary

SMILES: COC(=O)[C@@]1(O)C[C@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3
InChI: InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1
InChIKey: RXPRRQLKFXBCSJ-GIVPXCGWSA-N
DeepSMILES: COC=O)[C@@]O)C[C@]CC))CCCN[C@@H]6cn%10cccccc6c9CC%13
Scaffold Graph/Node/Bond level: c1ccc2c(c1)c1c3n2CCC2CCCN(CC1)C32
Scaffold Graph/Node level: C1CCC2C(C1)C1CCN3CCCC4CCN2C1C43
Scaffold Graph level: C1CC2CCC3C4CCCCC4C4CCC(C1)C2C34
Functional groups: COC(C)=O; CO; CN(C)C; cn(c)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Eburnan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma-Iboga hybrid type (Vinca alkaloids)
Synonymous chemical names:
Vincamine, vincamine
External chemical identifiers:
CID:CID_15376; ChEMBL:CHEMBL1165342; ChEBI:CHEBI:9985; ZINC:ZINC000001069082; FDASRS:996XVD0JHT; SureChEMBL:SCHEMBL147179; MolPort-002-510-941
Chemical structure download


Vincamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.45
Log P RDKit 2.95
Topological polar surface area (Å2) RDKit 54.7
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 3
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


Vincamine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.842739


Vincamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.43
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes


Vincamine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000614ENSG00000087460GNAS2778NPASS
TAR_EXP_000773ENSG00000169083AR367ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_001707ENSG00000121966CXCR47852ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000682ENSG00000137252HCRTR23062ChEMBL, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001294ENSG00000160013PTGIR5739ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_000487ENSG00000171051FPR12357ChEMBL, NPASS
TAR_EXP_000620ENSG00000119973PRLHR2834ChEMBL, NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000213ENSG00000147262GPR119139760ChEMBL, NPASS
TAR_EXP_000188ENSG00000188822CNR21269ChEMBL, NPASS
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL, NPASS
TAR_EXP_000179ENSG00000179934CCR81237ChEMBL, NPASS
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL, NPASS
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS