IMPPAT Phytochemical information: 
Moschamine
Moschamine
Summary

SMILES: COc1cc(/C=C/C(=O)NCCc2c[nH]c3c2cc(O)cc3)ccc1O
InChI: InChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+
InChIKey: WGHKJYWENWLOMY-XVNBXDOJSA-N
DeepSMILES: COccc/C=C/C=O)NCCcc[nH]cc5ccO)cc6)))))))))))))))ccc6O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)NCCc1c[nH]c2ccccc12
Scaffold Graph/Node level: OC(CCC1CCCCC1)NCCC1CNC2CCCCC12
Scaffold Graph level: CC(CCCC1CCC2CCCCC21)CCC1CCCCC1
Functional groups: cOC; c/C=C/C(=O)NC; c[nH]c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Tryptamines and derivatives
NP Classifier Biosynthetic pathway: Amino acids and Peptides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acid amides
Synonymous chemical names:
n-feruloylserotonin, n-feruloyl serotonin
External chemical identifiers:
CID:CID_5969616; ChEMBL:CHEMBL564482; ChEBI:CHEBI:85158; ZINC:ZINC000001587150; FDASRS:2PP8322487; SureChEMBL:SCHEMBL1809357; MolPort-039-338-449
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Moschamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.39
Log P RDKit 2.96
Topological polar surface area (Å2) RDKit 94.58
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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 17
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3
Moschamine
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.513112
Moschamine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.34
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Moschamine
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_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_001647ENSG00000077498TYR7299ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725ChEMBL