Asparagine

Identification

Generic Name
Asparagine
DrugBank Accession Number
DB00174
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
Approved, Investigational, Nutraceutical
Structure
Weight
Average: 132.1179
Monoisotopic: 132.053492132
Chemical Formula
C4H8N2O3
Synonyms
  • (2S)-2-amino-3-carbamoylpropanoic acid
  • (2S)-2,4-diamino-4-oxobutanoic acid
  • (S)-2-amino-3-carbamoylpropanoic acid
  • (S)-Asparagine
  • 2-Aminosuccinamic acid
  • alpha-aminosuccinamic acid
  • Asn
  • Asparagine
  • Aspartamic acid
  • L-2-aminosuccinamic acid
  • L-Asparagine
  • L-aspartic acid beta-amide
  • L-aspartic acid β-amide
  • α-aminosuccinamic acid

Pharmacology

Indication

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

A non-essential amino acid. Asparagine is critical for the production of the body's proteins, enzymes and muscle tissue. Supplements of this amino acid are claimed to balance nervous system function.

Mechanism of action

Asparagine, a non-essential amino acid is important in the metabolism of toxic ammonia in the body through the action of asparagine synthase which attaches ammonia to aspartic acid in an amidation reaction. Asparagine is also used as a structural component in many proteins.

TargetActionsOrganism
ASodium-coupled neutral amino acid transporters
inhibitor
Humans
UNeutral amino acid transporter B(0)Not AvailableHumans
UAsparagine synthetase [glutamine-hydrolyzing]Not AvailableHumans
UAsparagine--tRNA ligase, cytoplasmicNot AvailableHumans
NIsoaspartyl peptidase/L-asparaginase
substrate
Humans
UProbable asparagine--tRNA ligase, 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
PathwayCategory
Ammonia RecyclingMetabolic
Clarithromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
Arbekacin Action PathwayDrug action
Troleandomycin Action PathwayDrug action
Josamycin Action PathwayDrug action
Azithromycin Action PathwayDrug action
Clindamycin Action PathwayDrug action
Erythromycin Action PathwayDrug action
Kanamycin Action PathwayDrug action
Neomycin Action PathwayDrug action
Netilmicin Action PathwayDrug action
Streptomycin Action PathwayDrug action
Clomocycline Action PathwayDrug action
Tobramycin Action PathwayDrug action
Rolitetracycline Action PathwayDrug action
Aspartate MetabolismMetabolic
Canavan DiseaseDisease
HypoacetylaspartiaDisease
Telithromycin Action PathwayDrug action
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Demeclocycline Action PathwayDrug action
Doxycycline Action PathwayDrug action
Minocycline Action PathwayDrug action
Lymecycline Action PathwayDrug action
Tigecycline Action PathwayDrug action
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

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AMINOPLASMAL-10% E INFUSIONAsparagine (3.27 g/l) + Acetylcysteine (0.5 g/l) + Alanine (13.7 g/l) + Arginine (9.2 g/l) + Aspartic acid (1.3 g/l) + Glutamic acid (4.6 g/l) + Glycine (7.9 g/l) + Histidine (5.2 g/l) + Isoleucine (5.1 g/l) + Leucine (8.9 g/l) + Lysine hydrochloride (5.6 g/l) + Magnesium acetate (0.56 g/l) + Malic acid (1.01 g/l) + Methionine (3.8 g/l) + N-acetyltyrosine (1 g/l) + Ornithine hydrochloride (2.51 g/l) + Phenylalanine (5.1 g/l) + Potassium acetate (2.45 g/l) + Proline (8.9 g/l) + Serine (2.4 g/l) + Sodium acetate (3.95 g/l) + Sodium hydroxide (0.2 g/l) + Sodium phosphate, monobasic (1.4 g/l) + Threonine (4.1 g/l) + Tryptophan (1.8 g/l) + Tyrosine (0.3 g/l) + Valine (4.8 g/l)InjectionIntravenousB. BRAUN SINGAPORE PTE LTD1991-05-13Not applicableSingapore flag
AMINOPLASMAL-5% E INFUSIONAsparagine (1.64 g/1000ml) + Acetylcysteine (0.25 g/1000ml) + Alanine (6.85 g/1000ml) + Arginine (4.6 g/1000ml) + Aspartic acid (0.65 g/1000ml) + Glutamic acid (2.3 g/1000ml) + Glycine (3.95 g/1000ml) + Histidine (2.6 g/1000ml) + Isoleucine (2.55 g/1000ml) + Leucine (4.45 g/1000ml) + Lysine hydrochloride (2.8 g/1000ml) + Magnesium acetate (0.56 g/1000ml) + Malic acid (1.01 g/1000ml) + Methionine (1.9 g/1000ml) + N-acetyltyrosine (0.35 g/1000ml) + Ornithine hydrochloride (1.25 g/1000ml) + Phenylalanine (2.55 g/1000ml) + Potassium acetate (2.45 g/1000ml) + Proline (4.45 g/1000ml) + Serine (1.2 g/1000ml) + Sodium acetate (3.95 g/1000ml) + Sodium hydroxide (0.2 g/1000ml) + Sodium phosphate, monobasic (1.4 g/1000ml) + Threonine (2.05 g/1000ml) + Tryptophan (0.9 g/1000ml) + Tyrosine (0.3 g/1000ml) + Valine (2.4 g/1000ml)InjectionIntravenousB. BRAUN SINGAPORE PTE LTD1991-05-13Not applicableSingapore flag
EXODERMA Brightening Mellow FoamAsparagine (2 g/100g) + Glycerin (0.04 g/100g)GelTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag
EXODERMA Brightening Peeling GelAsparagine (2 g/100g) + Glycerin (0.04 g/100g)GelTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag
EXODERMA Calming Toner PadAsparagine (2 g/100g) + Glycerin (0.04 g/100g)LiquidTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EXODERMA Brightening Mellow FoamAsparagine (2 g/100g) + Glycerin (0.04 g/100g)GelTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag
EXODERMA Brightening Peeling GelAsparagine (2 g/100g) + Glycerin (0.04 g/100g)GelTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag
EXODERMA Calming Toner PadAsparagine (2 g/100g) + Glycerin (0.04 g/100g)LiquidTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag
The Classeum Co., Ltd.Asparagine (2 g/100g) + Glycerin (0.04 g/100g)GelTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag
The Classeum Co., Ltd.Asparagine (2 g/100g) + Glycerin (0.04 g/100g)GelTopicalThe Classeum Co., Ltd2022-12-182023-12-17US flag

Categories

Drug Categories
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
L-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 / Fatty acid / Fatty acyl
show 13 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
aspartate family amino acid, proteinogenic amino acid, L-alpha-amino acid, asparagine (CHEBI:17196) / Common amino acids (C00152)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5Z33R5TKO7
CAS number
70-47-3
InChI Key
DCXYFEDJOCDNAF-REOHCLBHSA-N
InChI
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
IUPAC Name
(2S)-2-amino-3-carbamoylpropanoic acid
SMILES
N[C@@H](CC(N)=O)C(O)=O

References

Synthesis Reference

Sang C. Park, "Pharmaceutical preparation containing L-aspartate or L-asparagine for preventing ethanol toxicity, and process for preparation thereof." U.S. Patent US5389359, issued November, 1991.

US5389359
General References
Not Available
Human Metabolome Database
HMDB0000168
KEGG Compound
C00152
PubChem Compound
6267
PubChem Substance
46507804
ChemSpider
6031
BindingDB
181137
RxNav
1157
ChEBI
58048
ChEMBL
CHEMBL58832
ZINC
ZINC000001532556
PharmGKB
PA164776968
PDBe Ligand
41Q
Wikipedia
Asparagine
PDB Entries
3x2o / 3x2p
MSDS
Download (72.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous
InjectionIntravenous0.5 g/l
InjectionIntravenous0.25 g/1000ml
GelTopical
LiquidTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)234-235 °CPhysProp
water solubility2.94E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.82CHMELIK,J ET AL. (1991)
logS-0.74ADME Research, USCD
pKa8.82 (at 18 °C)KORTUM,G ET AL (1961)
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
Polarizability11.68 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)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0159-0910000000-bedf57998656ab5ebc16
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0159-0910000000-4979c4d028d2dc931263
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0159-0910000000-b7ea3fef61f3940cbdda
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-9710000000-6d0afcbcc003347e598e
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0uxr-0910000000-2be567239bd3229b1ca1
GC-MS Spectrum - GC-MSGC-MSsplash10-02t9-0790000000-b8141f48cbebb90f683e
GC-MS Spectrum - GC-MSGC-MSsplash10-02t9-1790000000-1d12ed9b4fb2799da766
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-014u-0961000000-65a5c0999f17110c9939
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-00lr-1920000000-7864dbb1f685e64dd1cf
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-000i-1940000000-964ea25da2789805985a
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000f-9100000000-5881591331bd059b7e7d
GC-MS Spectrum - EI-BGC-MSsplash10-00lr-0930000000-79a089d9875e092dd7f2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-0910000000-bedf57998656ab5ebc16
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-0910000000-4979c4d028d2dc931263
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-0910000000-b7ea3fef61f3940cbdda
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-00di-4931100000-17f149310ce3a0f748d1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9710000000-6d0afcbcc003347e598e
GC-MS Spectrum - GC-MSGC-MSsplash10-0uxr-0910000000-2be567239bd3229b1ca1
GC-MS Spectrum - GC-MSGC-MSsplash10-02t9-0790000000-b8141f48cbebb90f683e
GC-MS Spectrum - GC-MSGC-MSsplash10-02t9-1790000000-1d12ed9b4fb2799da766
GC-MS Spectrum - GC-MSGC-MSsplash10-014u-0961000000-65a5c0999f17110c9939
GC-MS Spectrum - GC-MSGC-MSsplash10-00kr-0940000000-0e0e5c7bdbac5ea0e49e
GC-MS Spectrum - GC-MSGC-MSsplash10-00lr-1920000000-7864dbb1f685e64dd1cf
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-1940000000-964ea25da2789805985a
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0080-9400000000-e5c7e19f427eea6d71b0
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-afc1214100db1168b095
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00dl-9000000000-57e977cd87e9a86d482b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-6fb96f5aa291359dba29
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-76f11e6fe5657c35d15f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-e944486273dbfde4cae4
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-27ad91a86be0c4d86c3c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-b8b7a3431b66246ad613
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-03fa294ec740e189dd99
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-cee2081406fc25ab6169
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-001i-0900000000-cd79afa0c27f65e54adc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-01q9-0943200000-5a24322ba0ce2f410155
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0900000000-fc3086cc1bb0c06a4c11
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-3900000000-2d74d8232e7523f3b1c9
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-fa61c6fa9a87ce4905bb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-01q9-0942200000-757da8b3406485c997b0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-014i-9000000000-eac18512f2d22ab7a7ef
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0900000000-8df6d5b6cf94bf081c89
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-001i-0900000000-18079004a95c252da208
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0900000000-e6b1f9b4982e6cdc863d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-03di-5900000000-7b9c09b3b6de28972f97
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00dl-9100000000-2ea95ead344d62e230a4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-defacc365589bc4437d7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-fd60db4d5e35794c45ae
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-3900000000-fd0f1034b5c1e40435c0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-9100000000-ac6ee5b31d2ca5a78980
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-9000000000-3c04f1c797434daa6d1c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00di-9000000000-fea0e8fe2daca327892e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-00dl-9000000000-da4f011dc3ac5b143f29
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-001i-0900000000-8717d01ca62b4bbbbc5b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-e6b1f9b4982e6cdc863d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-5900000000-0cb113c77622352647eb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00dl-9100000000-2ea95ead344d62e230a4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-defacc365589bc4437d7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-fd60db4d5e35794c45ae
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-fc3086cc1bb0c06a4c11
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-3900000000-2d74d8232e7523f3b1c9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-fa61c6fa9a87ce4905bb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-eac18512f2d22ab7a7ef
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-8df6d5b6cf94bf081c89
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-001i-0900000000-18079004a95c252da208
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-3900000000-fd0f1034b5c1e40435c0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9100000000-ac6ee5b31d2ca5a78980
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-c6f09ae894f786971692
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-fea0e8fe2daca327892e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-9000000000-da4f011dc3ac5b143f29
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-0df05b2f1172c9a862e9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-27ad91a86be0c4d86c3c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-03fa294ec740e189dd99
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-cee2081406fc25ab6169
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-cd79afa0c27f65e54adc
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-123.9305101
predicted
DarkChem Lite v0.1.0
[M-H]-124.3906675
predicted
DarkChem Standard v0.1.0
[M-H]-123.9937101
predicted
DarkChem Lite v0.1.0
[M-H]-120.16135
predicted
DeepCCS 1.0 (2019)
[M+H]+124.2593101
predicted
DarkChem Lite v0.1.0
[M+H]+127.6950326
predicted
DarkChem Standard v0.1.0
[M+H]+124.5710101
predicted
DarkChem Lite v0.1.0
[M+H]+124.02746
predicted
DeepCCS 1.0 (2019)
[M+Na]+123.6796101
predicted
DarkChem Lite v0.1.0
[M+Na]+123.6385101
predicted
DarkChem Lite v0.1.0
[M+Na]+123.6230101
predicted
DarkChem Lite v0.1.0
[M+Na]+133.03358
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Literature referenced performed experiment on rats.
General Function
Functions as a sodium-dependent amino acid transporter. Mediates the saturable, pH-sensitive and electrogenic cotransport of glutamine and sodium ions with a stoichiometry of 1:1. May also transport small zwitterionic and aliphatic amino acids with a lower affinity. May supply glutamatergic and GABAergic neurons with glutamine which is required for the synthesis of the neurotransmitters glutamate and GABA.
Specific Function
Amino acid transmembrane transporter activity

Components:
References
  1. Keep RF, Xiang J: N-system amino acid transport at the blood--CSF barrier. J Neurochem. 1995 Dec;65(6):2571-6. doi: 10.1046/j.1471-4159.1995.65062571.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Sodium-dependent amino acids transporter that has a broad substrate specificity, with a preference for zwitterionic amino acids. It accepts as substrates all neutral amino acids, including glutamin...
Gene Name
SLC1A5
Uniprot ID
Q15758
Uniprot Name
Neutral amino acid transporter B(0)
Molecular Weight
56597.64 Da
References
  1. Dun Y, Mysona B, Itagaki S, Martin-Studdard A, Ganapathy V, Smith SB: Functional and molecular analysis of D-serine transport in retinal Muller cells. Exp Eye Res. 2007 Jan;84(1):191-9. Epub 2006 Nov 13. [Article]
  2. Oppedisano F, Pochini L, Galluccio M, Cavarelli M, Indiveri C: Reconstitution into liposomes of the glutamine/amino acid transporter from renal cell plasma membrane: functional characterization, kinetics and activation by nucleotides. Biochim Biophys Acta. 2004 Dec 15;1667(2):122-31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Not Available
Gene Name
ASNS
Uniprot ID
P08243
Uniprot Name
Asparagine synthetase [glutamine-hydrolyzing]
Molecular Weight
64369.39 Da
References
  1. Tesson AR, Soper TS, Ciustea M, Richards NG: Revisiting the steady state kinetic mechanism of glutamine-dependent asparagine synthetase from Escherichia coli. Arch Biochem Biophys. 2003 May 1;413(1):23-31. [Article]
  2. Fresquet V, Thoden JB, Holden HM, Raushel FM: Kinetic mechanism of asparagine synthetase from Vibrio cholerae. Bioorg Chem. 2004 Apr;32(2):63-75. [Article]
  3. Chaffei C, Pageau K, Suzuki A, Gouia H, Ghorbel MH, Masclaux-Daubresse C: Cadmium toxicity induced changes in nitrogen management in Lycopersicon esculentum leading to a metabolic safeguard through an amino acid storage strategy. Plant Cell Physiol. 2004 Nov;45(11):1681-93. [Article]
  4. Al Sarraj J, Vinson C, Thiel G: Regulation of asparagine synthetase gene transcription by the basic region leucine zipper transcription factors ATF5 and CHOP. Biol Chem. 2005 Sep;386(9):873-9. [Article]
  5. Iwamoto S, Mihara K, Downing JR, Pui CH, Campana D: Mesenchymal cells regulate the response of acute lymphoblastic leukemia cells to asparaginase. J Clin Invest. 2007 Apr;117(4):1049-57. Epub 2007 Mar 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nucleic acid binding
Specific Function
Not Available
Gene Name
NARS
Uniprot ID
O43776
Uniprot Name
Asparagine--tRNA ligase, cytoplasmic
Molecular Weight
62942.425 Da
References
  1. Iwasaki W, Sekine S, Kuroishi C, Kuramitsu S, Shirouzu M, Yokoyama S: Structural basis of the water-assisted asparagine recognition by asparaginyl-tRNA synthetase. J Mol Biol. 2006 Jul 7;360(2):329-42. Epub 2006 May 15. [Article]
  2. Iwamoto S, Mihara K, Downing JR, Pui CH, Campana D: Mesenchymal cells regulate the response of acute lymphoblastic leukemia cells to asparaginase. J Clin Invest. 2007 Apr;117(4):1049-57. Epub 2007 Mar 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Beta-aspartyl-peptidase activity
Specific Function
Has both L-asparaginase and beta-aspartyl peptidase activity. May be involved in the production of L-aspartate, which can act as an excitatory neurotransmitter in some brain regions. Is highly acti...
Gene Name
ASRGL1
Uniprot ID
Q7L266
Uniprot Name
Isoaspartyl peptidase/L-asparaginase
Molecular Weight
32054.325 Da
References
  1. Li W, Irani S, Crutchfield A, Hodge K, Matthews W, Patel P, Zhang YJ, Stone E: Intramolecular Cleavage of the hASRGL1 Homodimer Occurs in Two Stages. Biochemistry. 2016 Feb 16;55(6):960-9. doi: 10.1021/acs.biochem.5b01157. Epub 2016 Feb 2. [Article]
  2. Li W, Cantor JR, Yogesha SD, Yang S, Chantranupong L, Liu JQ, Agnello G, Georgiou G, Stone EM, Zhang Y: Uncoupling intramolecular processing and substrate hydrolysis in the N-terminal nucleophile hydrolase hASRGL1 by circular permutation. ACS Chem Biol. 2012 Nov 16;7(11):1840-7. doi: 10.1021/cb300232n. Epub 2012 Aug 29. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nucleic acid binding
Specific Function
Not Available
Gene Name
NARS2
Uniprot ID
Q96I59
Uniprot Name
Probable asparagine--tRNA ligase, mitochondrial
Molecular Weight
54089.64 Da
References
  1. Iwasaki W, Sekine S, Kuroishi C, Kuramitsu S, Shirouzu M, Yokoyama S: Structural basis of the water-assisted asparagine recognition by asparaginyl-tRNA synthetase. J Mol Biol. 2006 Jul 7;360(2):329-42. Epub 2006 May 15. [Article]
  2. Roy H, Becker HD, Reinbolt J, Kern D: When contemporary aminoacyl-tRNA synthetases invent their cognate amino acid metabolism. Proc Natl Acad Sci U S A. 2003 Aug 19;100(17):9837-42. Epub 2003 Jul 21. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42