IMPPAT Phytochemical information: 
N-Nitrosoguvacoline

N-Nitrosoguvacoline
Summary

SMILES: COC(=O)C1=CCCN(C1)N=O
InChI: InChI=1S/C7H10N2O3/c1-12-7(10)6-3-2-4-9(5-6)8-11/h3H,2,4-5H2,1H3
InChIKey: NXEUEKXJAAVKCT-UHFFFAOYSA-N
DeepSMILES: COC=O)C=CCCNC6)N=O
Scaffold Graph/Node/Bond level: C1=CCNCC1
Scaffold Graph/Node level: C1CCNCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CC=C(C(=O)OC)C; CN(N=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
n-nitrosoguvacoline
External chemical identifiers:
CID:CID_62103; ChEMBL:CHEMBL165231; ChEBI:CHEBI:82512; ZINC:ZINC000005700803
Chemical structure download


N-Nitrosoguvacoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 170.17
Log P RDKit 0.47
Topological polar surface area (Å2) RDKit 58.97
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 7
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


N-Nitrosoguvacoline
Drug-likeness properties
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 0.446244


N-Nitrosoguvacoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.02
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


N-Nitrosoguvacoline
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000332679CYP2A13700
ENSP00000301141CYP2A6728
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.