NAV

N-[O-Phosphono-Pyridoxyl]-Isoleucine

Identification

Generic Name
N-[O-Phosphono-Pyridoxyl]-Isoleucine
DrugBank Accession Number
DB02635
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 362.3154
Monoisotopic: 362.124287612
Chemical Formula
C14H23N2O7P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBranched-chain-amino-acid aminotransferase, mitochondrialNot AvailableHumans
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
Isoleucine and derivatives / D-alpha-amino acids / Monoalkyl phosphates / Methylpyridines / Hydroxypyridines / Aralkylamines / Heteroaromatic compounds / Amino acids / Monocarboxylic acids and derivatives / Dialkylamines
show 5 more
Substituents
Alkyl phosphate / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group
show 20 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
GZZDWFDWHXPWJK-QPUJVOFHSA-N
InChI
InChI=1S/C14H23N2O7P/c1-4-8(2)12(14(18)19)16-6-11-10(7-23-24(20,21)22)5-15-9(3)13(11)17/h5,8,12,16-17H,4,6-7H2,1-3H3,(H,18,19)(H2,20,21,22)/t8-,12+/m0/s1
IUPAC Name
(2R,3S)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]-3-methylpentanoic acid
SMILES
[H][C@](C)(CC)[C@@]([H])(NCC1=C(COP(O)(O)=O)C=NC(C)=C1O)C(O)=O

References

General References
Not Available
PubChem Compound
92282619
PubChem Substance
46508097
ChemSpider
26326995
ZINC
ZINC000005846701
PDBe Ligand
ILP
PDB Entries
1kt8 / 5wyf

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 Solubility0.691 mg/mLALOGPS
logP-0.15ALOGPS
logP-2.8Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.19Chemaxon
pKa (Strongest Basic)9.96Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area149.21 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity85.59 m3·mol-1Chemaxon
Polarizability34.51 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9463
Blood Brain Barrier-0.8309
Caco-2 permeable-0.6532
P-glycoprotein substrateSubstrate0.6502
P-glycoprotein inhibitor INon-inhibitor0.7836
P-glycoprotein inhibitor IINon-inhibitor0.936
Renal organic cation transporterNon-inhibitor0.9433
CYP450 2C9 substrateNon-substrate0.7817
CYP450 2D6 substrateNon-substrate0.786
CYP450 3A4 substrateNon-substrate0.5888
CYP450 1A2 substrateNon-inhibitor0.7439
CYP450 2C9 inhibitorNon-inhibitor0.7694
CYP450 2D6 inhibitorNon-inhibitor0.8393
CYP450 2C19 inhibitorNon-inhibitor0.6961
CYP450 3A4 inhibitorNon-inhibitor0.7777
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9042
Ames testNon AMES toxic0.6833
CarcinogenicityNon-carcinogens0.8378
BiodegradationNot ready biodegradable0.9508
Rat acute toxicity2.4958 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8187
hERG inhibition (predictor II)Non-inhibitor0.562
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-MSsplash10-0002-9033000000-ff7d4727126ba63977c9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-0069000000-5c53f922bfd8c9e79909
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ta-9103000000-f8f87aa204a164eeaed2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-1692000000-1abf390dd33d5f87f46b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-5b9c2629eda64da62458
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-cc4b8c1736e3705d9535
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-007a-1920000000-ad714a790616aba4999b
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]-176.29614
predicted
DeepCCS 1.0 (2019)
[M+H]+178.65417
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.20488
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Branched-chain-amino-acid aminotransferase, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
L-valine transaminase activity
Specific Function
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
Gene Name
BCAT2
Uniprot ID
O15382
Uniprot Name
Branched-chain-amino-acid aminotransferase, mitochondrial
Molecular Weight
44287.445 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 August 01, 2020 13:44