D-[3-hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-ylmethyl]-N,O-cycloserylamide

Identification

Generic Name
D-[3-hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-ylmethyl]-N,O-cycloserylamide
DrugBank Accession Number
DB02038
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 333.2344
Monoisotopic: 333.072586393
Chemical Formula
C11H16N3O7P
Synonyms
  • D-pyridoxyl-N,O-cycloserylamide-5-monophosphate

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAminodeoxychorismate lyaseNot AvailableEscherichia coli (strain K12)
UAlanine racemaseNot AvailableGeobacillus stearothermophilus
UUDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
U2,2-dialkylglycine decarboxylaseNot AvailablePseudomonas cepacia
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
Adverseeffects
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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
Alpha amino acids and derivatives / Monoalkyl phosphates / Methylpyridines / Hydroxypyridines / Aralkylamines / Oxazolidinones / Isoxazolidines / Heteroaromatic compounds / Oxacyclic compounds / Dialkylamines
show 5 more
Substituents
Alkyl phosphate / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Heteroaromatic compound
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aminoalkylpyridine, monoalkyl phosphate, oxazolidines (CHEBI:43639)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NNRZSZJOQKAGTO-SECBINFHSA-N
InChI
InChI=1S/C11H16N3O7P/c1-6-10(15)8(3-13-9-5-20-14-11(9)16)7(2-12-6)4-21-22(17,18)19/h2,9,13,15H,3-5H2,1H3,(H,14,16)(H2,17,18,19)/t9-/m1/s1
IUPAC Name
{[5-hydroxy-6-methyl-4-({[(4R)-3-oxo-1,2-oxazolidin-4-yl]amino}methyl)pyridin-3-yl]methoxy}phosphonic acid
SMILES
CC1=NC=C(COP(O)(O)=O)C(CN[C@@H]2CONC2=O)=C1O

References

General References
Not Available
PubChem Compound
445005
PubChem Substance
46509108
ChemSpider
392768
ZINC
ZINC000002043174
PDBe Ligand
DCS
PDB Entries
1d7s / 1epv / 1i2l / 1mdz / 1niu / 1vfs / 1vft / 2daa / 2rjh / 3e6e
show 5 more

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 Solubility2.21 mg/mLALOGPS
logP-1.4ALOGPS
logP-3.4ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)7.99ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area150.24 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.34 m3·mol-1ChemAxon
Polarizability29.33 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Involved in the biosynthesis of p-aminobenzoate (PABA), a precursor of tetrahydrofolate. Converts 4-amino-4-deoxychorismate into 4-aminobenzoate (PABA) and pyruvate.
Gene Name
pabC
Uniprot ID
P28305
Uniprot Name
Aminodeoxychorismate lyase
Molecular Weight
29714.78 Da
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]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Transaminase activity
Specific Function
Catalyzes the conversion of UDP-4-keto-arabinose (UDP-Ara4O) to UDP-4-amino-4-deoxy-L-arabinose (UDP-L-Ara4N). The modified arabinose is attached to lipid A and is required for resistance to polymy...
Gene Name
arnB
Uniprot ID
Q8ZNF3
Uniprot Name
UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase
Molecular Weight
41164.65 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]
Kind
Protein
Organism
Pseudomonas cepacia
Pharmacological action
Unknown
General Function
Transaminase activity
Specific Function
The dialkylglycine decarboxylase is of interest because it normally catalyzes both decarboxylation and amino transfer. It may be more properly described as a decarboxylating aminotransferase rather...
Gene Name
dgdA
Uniprot ID
P16932
Uniprot Name
2,2-dialkylglycine decarboxylase
Molecular Weight
46443.91 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 on June 13, 2005 13:24 / Updated on June 12, 2020 16:52