NAV

2-amino-3-[4-hydroxy-6-oxo-3-(2-phenyl-cyclopropylimino)-cyclohexa-1,4-dienyl]-propionic acid

Identification

Generic Name
2-amino-3-[4-hydroxy-6-oxo-3-(2-phenyl-cyclopropylimino)-cyclohexa-1,4-dienyl]-propionic acid
DrugBank Accession Number
DB01657
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 328.3624
Monoisotopic: 328.142307138
Chemical Formula
C18H20N2O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPrimary amine oxidaseNot AvailableEscherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QDTWKLJWNHRCPJ-HMMYKYKNSA-N
InChI
InChI=1S/C18H20N2O4/c19-13(18(23)24)6-11-7-15(17(22)9-16(11)21)20-14-8-12(14)10-4-2-1-3-5-10/h1-5,9,11-14,22H,6-8,19H2,(H,23,24)/b20-15+
IUPAC Name
2-amino-3-[(5E)-4-hydroxy-2-oxo-5-[(2-phenylcyclopropyl)imino]cyclohex-3-en-1-yl]propanoic acid
SMILES
NC(CC1C\C(=N/C2CC2C2=CC=CC=C2)C(O)=CC1=O)C(O)=O

References

General References
Not Available
PubChem Compound
23644144
PubChem Substance
46505620
PDBe Ligand
TYT
PDB Entries
1lvn

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.166 mg/mLALOGPS
logP-1ALOGPS
logP-2Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)1.86Chemaxon
pKa (Strongest Basic)9.12Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area112.98 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity89.25 m3·mol-1Chemaxon
Polarizability34.41 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8299
Blood Brain Barrier-0.8147
Caco-2 permeable-0.7097
P-glycoprotein substrateSubstrate0.5505
P-glycoprotein inhibitor INon-inhibitor0.902
P-glycoprotein inhibitor IINon-inhibitor0.7943
Renal organic cation transporterNon-inhibitor0.8502
CYP450 2C9 substrateNon-substrate0.7453
CYP450 2D6 substrateNon-substrate0.8561
CYP450 3A4 substrateNon-substrate0.6426
CYP450 1A2 substrateNon-inhibitor0.7986
CYP450 2C9 inhibitorNon-inhibitor0.8522
CYP450 2D6 inhibitorNon-inhibitor0.8734
CYP450 2C19 inhibitorNon-inhibitor0.8207
CYP450 3A4 inhibitorNon-inhibitor0.8357
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8883
Ames testNon AMES toxic0.7167
CarcinogenicityNon-carcinogens0.8089
BiodegradationNot ready biodegradable0.9795
Rat acute toxicity2.4434 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Non-inhibitor0.9373
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-02w9-0498000000-5bb9cbd818507eea7635
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00or-0689000000-81b30ad53de4401a6e55
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1891000000-7c6d7e0cc553dc7b1f9d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gdi-0292000000-6baac0a27c93fab3dd27
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-9732000000-598da56dc58a65ea2fce
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0930000000-ae3df81616e45edf8659
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-176.56071
predicted
DeepCCS 1.0 (2019)
[M+H]+178.91891
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.0974
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Primary amine oxidase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
The enzyme prefers aromatic over aliphatic amines.
Gene Name
tynA
Uniprot ID
P46883
Uniprot Name
Primary amine oxidase
Molecular Weight
84378.17 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51