NAV

N-(5'-Phosphopyridoxyl)-D-Alanine

Identification

Generic Name
N-(5'-Phosphopyridoxyl)-D-Alanine
DrugBank Accession Number
DB01993
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 320.2356
Monoisotopic: 320.07733742
Chemical Formula
C11H17N2O7P
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
Alanine and derivatives / D-alpha-amino acids / Aralkylamines / Monoalkyl phosphates / Methylpyridines / Hydroxypyridines / Heteroaromatic compounds / Amino acids / Dialkylamines / Monocarboxylic acids and derivatives
show 6 more
Substituents
Alanine or derivatives / Alkyl phosphate / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monohydroxypyridine, D-alpha-amino acid, D-alanine derivative, phosphate monoester (CHEBI:44743)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
WACJCHFWJNNBPR-SSDOTTSWSA-N
InChI
InChI=1S/C11H17N2O7P/c1-6-10(14)9(4-13-7(2)11(15)16)8(3-12-6)5-20-21(17,18)19/h3,7,13-14H,4-5H2,1-2H3,(H,15,16)(H2,17,18,19)/t7-/m1/s1
IUPAC Name
(2R)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]propanoic acid
SMILES
C[C@@H](NCC1=C(O)C(C)=NC=C1COP(O)(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
446862
PubChem Substance
46505701
ChemSpider
394107
ChEBI
44743
ZINC
ZINC000002047235
PDBe Ligand
PDD
PDB Entries
1l6g / 2bmk / 2zpu / 2zr8 / 3daa

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 Solubility1.48 mg/mLALOGPS
logP-1.7ALOGPS
logP-4.2Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.03Chemaxon
pKa (Strongest Basic)9.58Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area149.21 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity71.99 m3·mol-1Chemaxon
Polarizability28.92 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9868
Blood Brain Barrier-0.7645
Caco-2 permeable-0.6694
P-glycoprotein substrateSubstrate0.6849
P-glycoprotein inhibitor INon-inhibitor0.9108
P-glycoprotein inhibitor IINon-inhibitor0.968
Renal organic cation transporterNon-inhibitor0.9081
CYP450 2C9 substrateNon-substrate0.7294
CYP450 2D6 substrateNon-substrate0.7888
CYP450 3A4 substrateNon-substrate0.6235
CYP450 1A2 substrateNon-inhibitor0.8007
CYP450 2C9 inhibitorNon-inhibitor0.8457
CYP450 2D6 inhibitorNon-inhibitor0.8547
CYP450 2C19 inhibitorNon-inhibitor0.7895
CYP450 3A4 inhibitorNon-inhibitor0.9097
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.931
Ames testNon AMES toxic0.6835
CarcinogenicityNon-carcinogens0.8853
BiodegradationNot ready biodegradable0.9293
Rat acute toxicity2.1957 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.872
hERG inhibition (predictor II)Non-inhibitor0.5691
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-MSsplash10-002b-9151000000-f01fab7972d9ceff757b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ea-0194000000-33ada4d7f42985638e0e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00os-9023000000-8ba8199c9eece7fba061
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1981000000-991f4ae62f1f238c7537
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-4bf2b9a14f4e1c8fc62a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-61ba1902bf2e52d41e84
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-7900000000-5ec7ce8dfc818302eebb
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]-156.43199
predicted
DeepCCS 1.0 (2019)
[M+H]+158.79001
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.05556
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