Asparagine

l-Asparagine
	Skeletal formula of L-asparagine
	Skeletal formula of L-asparagine under physiological conditions
Ball-and-stick model	Space-filling model
Names
	IUPAC name Asparagine
	Systematic IUPAC name 2-Amino-3-carbamoylpropanoic acid
Identifiers
CAS Number	70-47-3 ;
3D model (JSmol)	Interactive image; Zwitterion: Interactive image;
ChEBI	CHEBI:17196 ;
ChEMBL	ChEMBL58832 ;
ChemSpider	6031 ;
DrugBank	DB03943 ;
ECHA InfoCard	100.019.565
EC Number	200-735-9;
IUPHAR/BPS	4533;
KEGG	C00152 ;
PubChem CID	236;
UNII	5Z33R5TKO7 ;
CompTox Dashboard (EPA)	DTXSID30859927 ;
	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 Key: DCXYFEDJOCDNAF-REOHCLBHSA-N ; InChI=1/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1 Key: DCXYFEDJOCDNAF-REOHCLBHBD;
	SMILES O=C(N)C[C@H](N)C(=O)O; Zwitterion: O=C(N)C[C@H]([NH3+])C(=O)[O-];
Properties
Chemical formula	C4H8N2O3
Molar mass	132.119 g·mol−1
Appearance	white crystals
Density	1.543 g/cm3
Melting point	234 °C (453 °F; 507 K)
Boiling point	438 °C (820 °F; 711 K)
Solubility in water	2.94 g/100 mL
Solubility	soluble in acids, bases, negligible in methanol, ethanol, ether, benzene
log P	−3.82
Acidity (pKa)	2.1 (carboxyl; 20 °C, H2O); 8.80 (amino; 20 °C, H2O);
Magnetic susceptibility (χ)	−69.5·10−6 cm3/mol
Structure
Crystal structure	orthorhombic
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−789.4 kJ/mol
Hazards
NFPA 704 (fire diamond)	1 0 0
Flash point	219 °C (426 °F; 492 K)
Safety data sheet (SDS)	Sigma-Alrich
Supplementary data page
	Asparagine (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Asparagine (symbol Asn or N^[2]) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH⁺
₃ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO⁻ form under biological conditions), and a side chain carboxamide, classifying it as a polar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it. It is encoded by the codons AAU and AAC.

The one-letter symbol N for asparagine was assigned arbitrarily,^[3] with the proposed mnemonic asparagiNe;^[4]

^ Haynes WM, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
^ "IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences". Journal of Biological Chemistry. 243 (13): 3557–3559. 10 July 1968. doi:10.1016/S0021-9258(19)34176-6. Archived from the original on 20 February 2024. Retrieved 21 February 2024.
^ Adoga, Godwin I; Nicholson, Bh (January 1988). "Letters to the editor". Biochemical Education. 16 (1): 49. doi:10.1016/0307-4412(88)90026-X. Archived from the original on 2024-02-20. Retrieved 2024-02-21.

[CRC97-1] Haynes WM, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.

[2] "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.

[:0-3] "IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences". Journal of Biological Chemistry. 243 (13): 3557–3559. 10 July 1968. doi:10.1016/S0021-9258(19)34176-6. Archived from the original on 20 February 2024. Retrieved 21 February 2024.

[:2-4] Adoga, Godwin I; Nicholson, Bh (January 1988). "Letters to the editor". Biochemical Education. 16 (1): 49. doi:10.1016/0307-4412(88)90026-X. Archived from the original on 2024-02-20. Retrieved 2024-02-21.

[1]

[2]

[3]

[4]