NAV

{1-[(3-Hydroxy-Methyl-5-Phosphonooxy-Methyl-Pyridin-4-Ylmethyl)-Amino]-Ethyl}-Phosphonic Acid

Identification

Generic Name
{1-[(3-Hydroxy-Methyl-5-Phosphonooxy-Methyl-Pyridin-4-Ylmethyl)-Amino]-Ethyl}-Phosphonic Acid
DrugBank Accession Number
DB03327
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 356.206
Monoisotopic: 356.053838586
Chemical Formula
C10H18N2O8P2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAlanine racemaseNot AvailableGeobacillus stearothermophilus
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridoxamines
Direct Parent
Pyridoxamine 5'-phosphates
Alternative Parents
Monoalkyl phosphates / Methylpyridines / Hydroxypyridines / Organic phosphonic acids / Heteroaromatic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds
show 2 more
Substituents
Alkyl phosphate / Amine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyridine / Methylpyridine / Monoalkyl phosphate / Organic nitrogen compound
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
WHDCJKAOZPBUAY-SSDOTTSWSA-N
InChI
InChI=1S/C10H18N2O8P2/c1-6-10(13)9(4-12-7(2)21(14,15)16)8(3-11-6)5-20-22(17,18)19/h3,7,12-13H,4-5H2,1-2H3,(H2,14,15,16)(H2,17,18,19)/t7-/m1/s1
IUPAC Name
[(1R)-1-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]ethyl]phosphonic acid
SMILES
[H][C@@](C)(NCC1=C(COP(O)(O)=O)C=NC(C)=C1O)P(O)(O)=O

References

General References
Not Available
PubChem Compound
444528
PubChem Substance
46506756
ChemSpider
392441
ZINC
ZINC000002047885
PDBe Ligand
IN5
PDB Entries
1bd0 / 2vd9 / 4itx / 4xbj

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 Solubility3.98 mg/mLALOGPS
logP-0.7ALOGPS
logP-5.2Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)-0.61Chemaxon
pKa (Strongest Basic)8.99Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area169.44 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity76.74 m3·mol-1Chemaxon
Polarizability30.39 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.974
Blood Brain Barrier-0.5984
Caco-2 permeable-0.6514
P-glycoprotein substrateSubstrate0.6867
P-glycoprotein inhibitor INon-inhibitor0.8972
P-glycoprotein inhibitor IINon-inhibitor0.9639
Renal organic cation transporterNon-inhibitor0.8874
CYP450 2C9 substrateNon-substrate0.7363
CYP450 2D6 substrateNon-substrate0.7657
CYP450 3A4 substrateNon-substrate0.6172
CYP450 1A2 substrateNon-inhibitor0.8353
CYP450 2C9 inhibitorNon-inhibitor0.859
CYP450 2D6 inhibitorNon-inhibitor0.8533
CYP450 2C19 inhibitorNon-inhibitor0.8027
CYP450 3A4 inhibitorNon-inhibitor0.9258
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9332
Ames testNon AMES toxic0.7009
CarcinogenicityNon-carcinogens0.8731
BiodegradationNot ready biodegradable0.97
Rat acute toxicity2.1051 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7279
hERG inhibition (predictor II)Inhibitor0.5067
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-9262000000-426c33eb17998882847e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0149000000-ed823f614ac55ca0d1a8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-3009000000-893610e903a788b8d364
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0790000000-52523f3c4565baef5e62
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-2f4faac46153edd47ec6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9001000000-b2e1fbe9c42956f45703
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-9da558e076e59b48813f
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]-167.85033
predicted
DeepCCS 1.0 (2019)
[M+H]+170.20833
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.7777
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Alanine racemase
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the interconversion of L-alanine and D-alanine. Also weakly active on serine.
Gene Name
alr
Uniprot ID
P10724
Uniprot Name
Alanine racemase
Molecular Weight
43592.715 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 16:52