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

Similar Structures

Weight: Average: 333.2344
Monoisotopic: 333.072586393
Chemical Formula: C₁₁H₁₆N₃O₇P

Synonyms

D-pyridoxyl-N,O-cycloserylamide-5-monophosphate

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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

Target	Actions	Organism
U2,2-dialkylglycine decarboxylase	Not Available	Pseudomonas cepacia
UAlanine racemase	Not Available	Geobacillus stearothermophilus
UUDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase	Not Available	Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UAminodeoxychorismate lyase	Not Available	Escherichia 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

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

External Links

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 …

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

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

Property	Value	Source
Water Solubility	2.21 mg/mL	ALOGPS
logP	-1.4	ALOGPS
logP	-3.4	Chemaxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.74	Chemaxon
pKa (Strongest Basic)	7.82	Chemaxon
Physiological Charge	-2	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	5	Chemaxon
Polar Surface Area	150.24 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	73.34 m³·mol^-1	Chemaxon
Polarizability	29.32 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0002-9182000000-b4ae91119f3eb340f991
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0029000000-ce946a4234becef286a6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00aj-9076000000-ea22dde7728f60654eff
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0972000000-19788b228b9ea3cdc59d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-9000000000-fc7bc3314809a5881d48
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-9000000000-f513284b7d8426dfc21e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-006t-4910000000-70cee6f6a9c9131257b1
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	160.20921	predicted	DeepCCS 1.0 (2019)
[M+H]+	162.56721	predicted	DeepCCS 1.0 (2019)
[M+Na]+	169.92062	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. 2,2-dialkylglycine decarboxylase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details2. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details3. UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details4. Aminodeoxychorismate lyase

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

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52