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D-Asparagine

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Overview

Structure
DrugBank ID
DB03943
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
D-Asparagine
DrugBank Accession Number
DB03943
Background

A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed)

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 132.1179
Monoisotopic: 132.053492132
Chemical Formula
C4H8N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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 asparagine and derivatives. These are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Asparagine and derivatives
Alternative Parents
D-alpha-amino acids / Fatty amides / Fatty acids and conjugates / Primary carboxylic acid amides / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Asparagine or derivatives / Carbonyl group / Carboxamide group / Carboxylic acid / D-alpha-amino acid / Fatty acid
show 13 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-alpha-amino acid, asparagine (CHEBI:28159) / Other amino acids (C01905)
Affected organisms
Not Available

Chemical Identifiers

UNII
T6QV1010K6
CAS number
2058-58-4
InChI Key
DCXYFEDJOCDNAF-UWTATZPHSA-N
InChI
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1
IUPAC Name
(2R)-2-amino-3-carbamoylpropanoic acid
SMILES
N[C@H](CC(N)=O)C(O)=O

References

Synthesis Reference

Hans Iding, "Process for the preparation of D-asparagine derivatives." U.S. Patent US20010049127, issued December 06, 2001.

US20010049127
General References
Not Available
Human Metabolome Database
HMDB0033780
KEGG Compound
C01905
PubChem Compound
439600
PubChem Substance
46507204
ChemSpider
388679
ChEBI
74337
ChEMBL
CHEMBL1232369
ZINC
ZINC000001529313
PDBe Ligand
DSG
PDB Entries
1t5m / 1t5n / 1xt7 / 2igz / 2ih0 / 2jue / 2kql / 2lbz / 2q33 / 2rqo …
show 82 more

Clinical Trials

Clinical Trials
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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 Solubility168.0 mg/mLALOGPS
logP-3.4ALOGPS
logP-4.3Chemaxon
logS0.1ALOGPS
pKa (Strongest Acidic)2Chemaxon
pKa (Strongest Basic)8.43Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area106.41 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity28.35 m3·mol-1Chemaxon
Polarizability11.77 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5517
Blood Brain Barrier+0.8465
Caco-2 permeable-0.8457
P-glycoprotein substrateNon-substrate0.8088
P-glycoprotein inhibitor INon-inhibitor0.9513
P-glycoprotein inhibitor IINon-inhibitor0.9935
Renal organic cation transporterNon-inhibitor0.9753
CYP450 2C9 substrateNon-substrate0.8403
CYP450 2D6 substrateNon-substrate0.8337
CYP450 3A4 substrateNon-substrate0.7705
CYP450 1A2 substrateNon-inhibitor0.9617
CYP450 2C9 inhibitorNon-inhibitor0.9717
CYP450 2D6 inhibitorNon-inhibitor0.9669
CYP450 2C19 inhibitorNon-inhibitor0.9763
CYP450 3A4 inhibitorNon-inhibitor0.9079
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9922
Ames testNon AMES toxic0.6386
CarcinogenicityNon-carcinogens0.8619
BiodegradationReady biodegradable0.8549
Rat acute toxicity1.4003 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9979
hERG inhibition (predictor II)Non-inhibitor0.9786
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-MSsplash10-000f-9100000000-5881591331bd059b7e7d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-9000000000-488e4a22b8c8745b59ac
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-5900000000-784c6c0863794256a97a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-fe9c23978b28834e4a49
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-b976e3a8d8d36823ea33
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00r6-9000000000-96abad6088768dedf5f6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-14b587fed3bad0f83b1a
13C NMR Spectrum1D NMRNot Applicable
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]-124.2633101
predicted
DarkChem Lite v0.1.0
[M-H]-125.2403101
predicted
DarkChem Lite v0.1.0
[M-H]-119.3737
predicted
DeepCCS 1.0 (2019)
[M+H]+124.9633101
predicted
DarkChem Lite v0.1.0
[M+H]+125.0364101
predicted
DarkChem Lite v0.1.0
[M+H]+123.013504
predicted
DeepCCS 1.0 (2019)
[M+Na]+124.4323101
predicted
DarkChem Lite v0.1.0
[M+Na]+124.9890101
predicted
DarkChem Lite v0.1.0
[M+Na]+131.76166
predicted
DeepCCS 1.0 (2019)

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