NAV

(2R)-4,4-dihydroxy-5-nitro-2-(phenylmethyl)pentanoic acid

Identification

Generic Name
(2R)-4,4-dihydroxy-5-nitro-2-(phenylmethyl)pentanoic acid
DrugBank Accession Number
DB07484
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 269.2506
Monoisotopic: 269.089937217
Chemical Formula
C12H15NO6
Synonyms
Not Available
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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
TargetActionsOrganism
UCarboxypeptidase A1Not 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 phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Phenylpropanoic acids
Sub Class
Not Available
Direct Parent
Phenylpropanoic acids
Alternative Parents
Benzene and substituted derivatives / C-nitro compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carbonyl hydrates / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
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Substituents
3-phenylpropanoic-acid / Allyl-type 1,3-dipolar organic compound / Aromatic homomonocyclic compound / Benzenoid / C-nitro compound / Carbonyl group / Carbonyl hydrate / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative
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Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CGGNZMVODZPHHK-SNVBAGLBSA-N
InChI
InChI=1S/C12H15NO6/c14-11(15)10(6-9-4-2-1-3-5-9)7-12(16,17)8-13(18)19/h1-5,10,16-17H,6-8H2,(H,14,15)/t10-/m1/s1
IUPAC Name
(2R)-2-benzyl-4,4-dihydroxy-5-nitropentanoic acid
SMILES
[H][C@@](CC1=CC=CC=C1)(CC(O)(O)C[N+]([O-])=O)C(O)=O

References

General References
Not Available
PubChem Compound
44176354
PubChem Substance
99443955
ChemSpider
25056642
ZINC
ZINC000039258292
PDBe Ligand
BPX
PDB Entries
3fx6

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 Solubility0.974 mg/mLALOGPS
logP0.24ALOGPS
logP1.11Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.1Chemaxon
pKa (Strongest Basic)-4.5Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area120.9 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity63.93 m3·mol-1Chemaxon
Polarizability25.08 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6433
Blood Brain Barrier+0.5896
Caco-2 permeable-0.5831
P-glycoprotein substrateNon-substrate0.6135
P-glycoprotein inhibitor INon-inhibitor0.9203
P-glycoprotein inhibitor IINon-inhibitor0.8949
Renal organic cation transporterNon-inhibitor0.8723
CYP450 2C9 substrateNon-substrate0.8101
CYP450 2D6 substrateNon-substrate0.8371
CYP450 3A4 substrateNon-substrate0.6129
CYP450 1A2 substrateNon-inhibitor0.791
CYP450 2C9 inhibitorNon-inhibitor0.8881
CYP450 2D6 inhibitorNon-inhibitor0.8817
CYP450 2C19 inhibitorNon-inhibitor0.8062
CYP450 3A4 inhibitorNon-inhibitor0.961
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9605
Ames testNon AMES toxic0.5344
CarcinogenicityNon-carcinogens0.7242
BiodegradationReady biodegradable0.5471
Rat acute toxicity2.2995 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9056
hERG inhibition (predictor II)Non-inhibitor0.9054
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-MSsplash10-06r6-8930000000-991f5fbe9466eb77e7d5
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]-148.06236
predicted
DeepCCS 1.0 (2019)
[M+H]+151.64394
predicted
DeepCCS 1.0 (2019)
[M+Na]+160.459
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Carboxypeptidase A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Carboxypeptidase that catalyzes the release of a C-terminal amino acid, but has little or no action with -Asp, -Glu, -Arg, -Lys or -Pro.
Gene Name
CPA1
Uniprot ID
P15085
Uniprot Name
Carboxypeptidase A1
Molecular Weight
47139.86 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:22 / Updated at June 12, 2020 16:52