L-ASPARAGINE
General Information
| Mainterm | L-ASPARAGINE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 70-47-3 |
| Regnum |
172.320 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6267 |
| IUPAC Name | (2S)-2,4-diamino-4-oxobutanoic acid |
| 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 |
| InChI Key | DCXYFEDJOCDNAF-REOHCLBHSA-N |
| Canonical SMILES | C(C(C(=O)O)N)C(=O)N |
| Molecular Formula | C4H8N2O3 |
| Wikipedia | L-Asparagine |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 132.119 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Complexity | 134.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B j M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A Q C A A A C C j B g A Q A C A B A A g A I A A G Q G A A A A A A A A A A A A I G A A A A C A B g A w A A A Q A A E E A A A A A A n A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 106.0 |
| Monoisotopic Mass | 132.053 |
| Exact Mass | 132.053 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8465 |
| Human Intestinal Absorption | HIA+ | 0.5517 |
| Caco-2 Permeability | Caco2- | 0.8457 |
| P-glycoprotein Substrate | Non-substrate | 0.8088 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9513 |
| Non-inhibitor | 0.9935 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9753 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6875 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8403 |
| CYP450 2D6 Substrate | Non-substrate | 0.8337 |
| CYP450 3A4 Substrate | Non-substrate | 0.7705 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9617 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9717 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9669 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9763 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9079 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9922 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9979 |
| Non-inhibitor | 0.9786 | |
| AMES Toxicity | Non AMES toxic | 0.6386 |
| Carcinogens | Non-carcinogens | 0.8619 |
| Fish Toxicity | Low FHMT | 0.8147 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9915 |
| Honey Bee Toxicity | Low HBT | 0.7896 |
| Biodegradation | Ready biodegradable | 0.8549 |
| Acute Oral Toxicity | IV | 0.5266 |
| Carcinogenicity (Three-class) | Non-required | 0.7261 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.6779 | LogS |
| Caco-2 Permeability | -0.4112 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.4003 | LD50, mol/kg |
| Fish Toxicity | 2.5755 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.0838 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | 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. |
| Metabolism | None |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Asparagine and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Asparagine or derivatives - Alpha-amino acid - L-alpha-amino acid - Fatty amide - Fatty acyl - Fatty acid - Carboxamide group - Amino acid - Primary carboxylic acid amide - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Primary aliphatic amine - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Amine - Aliphatic acyclic compound |
| 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. |
From ClassyFire
Targets
- General Function:
- Protein homodimerization activity
- Gene Name:
- ASNS
- Uniprot ID:
- P08243
- Molecular Weight:
- 64369.39 Da
References
- 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. [17380207 ]
- General Function:
- Nucleic acid binding
- Gene Name:
- NARS
- Uniprot ID:
- O43776
- Molecular Weight:
- 62942.425 Da
References
- 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. [16753178 ]
- 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 active with L-Asp beta-methyl ester. Besides, has catalytic activity toward beta-aspartyl dipeptides and their methyl esters, including beta-L-Asp-L-Phe, beta-L-Asp-L-Phe methyl ester (aspartame), beta-L-Asp-L-Ala, beta-L-Asp-L-Leu and beta-L-Asp-L-Lys. Does not have aspartylglucosaminidase activity and is inactive toward GlcNAc-L-Asn. Likewise, has no activity toward glutamine.
- Gene Name:
- ASRGL1
- Uniprot ID:
- Q7L266
- Molecular Weight:
- 32054.325 Da
References
- 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. [17016423 ]
- 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 glutamine, asparagine, and branched-chain and aromatic amino acids, and excludes methylated, anionic, and cationic amino acids. May also be activated by insulin. Through binding of the fusogenic protein syncytin-1/ERVW-1 may mediate trophoblasts syncytialization, the spontaneous fusion of their plasma membranes, an essential process in placental development (PubMed:10708449, PubMed:23492904). Acts as a cell surface receptor for feline endogenous virus RD114, baboon M7 endogenous virus and type D simian retroviruses (PubMed:10051606, PubMed:10196349).
- Gene Name:
- SLC1A5
- Uniprot ID:
- Q15758
- Molecular Weight:
- 56597.64 Da
References
- 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. [15581847 ]
- General Function:
- Nucleic acid binding
- Gene Name:
- NARS2
- Uniprot ID:
- Q96I59
- Molecular Weight:
- 54089.64 Da
References
- 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. [12874385 ]
- General Function:
- Symporter activity
- Specific Function:
- Sodium-dependent amino acid/proton antiporter. Mediates electrogenic cotransport of glutamine and sodium ions in exchange for protons. Also recognizes histidine, asparagine and alanine. May mediate amino acid transport in either direction under physiological conditions. May play a role in nitrogen metabolism and synaptic transmission.
- Gene Name:
- SLC38A3
- Uniprot ID:
- Q99624
- Molecular Weight:
- 55772.405 Da
References
- 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. [17016423 ]
From T3DB