CAS 2058-58-4 D-Asparagine (HCID 439600)

Overview

D-asparagine is an optically active form of asparagine having D-configuration. It is a D-alpha-amino acid and an asparagine. It is a conjugate base of a D-asparaginium. It is a conjugate acid of a D-asparaginate. It is an enantiomer of a L-asparagine. It is a tautomer of a D-asparagine zwitterion.

Names & identifiers

Preferred name: D-Asparagine
IUPAC: (2R)-2,4-diamino-4-oxobutanoic acid
English name: D-(-)-Asparagine monohydrate
Molecular formula: C4H8N2O3
Molecular weight: 132.12

Names & synonyms

D-Asparagine2058-58-4(2R)-2,4-diamino-4-oxobutanoic acid(2R)-2-amino-3-carbamoylpropanoic acidAsparagine, D-D-aspartic acid beta-amideD-2-aminosuccinamic acidD-AsparaginUNII-T6QV1010K6(2R)-4-amino-2-ammonio-4-oxobutanoateEINECS 218-163-3(R)-2-amino-3-carbamoylpropanoic acid

Show more names

ASPARAGINED-AsnH-D-Asn-OHD-Asn-OHD-Asn.H2OD-asparagine anhydrousD-AsparagD-ASPARGINED-Asn-OH·H2O

CHEBI:28159DTXSID30872479D-asparagine zwitterionCHEBI:74337(2R)-4-amino-2-azaniumyl-4-oxobutanoateRefChem:130509DTXCID70820136218-163-3

Database identifiers

CAS: 2058-58-4
PubChem CID: 439600
DTXSID: DTXSID30872479
ChEMBL: CHEMBL1232369
ChEBI: CHEBI:28159
UNII: T6QV1010K6
EC Number: 218-163-3
Nikkaji: J9.207J

Properties

Computed structural properties

XLogP: -3.4
Topological polar surface area: 106 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 9
Formal charge: 0
Complexity: 134

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Melting Point234 - 235 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 280 °C · 280 °C (dec.) (lit.)
alpha: -35 · -35 º (c=5, 5M HCl)
Boiling point: 438 · 438.0±40.0 °C(Predicted)
Density: 1.404 · 1.404±0.06 g/cm3(Predicted)
storage temp.: 0 · Store at 0-5°C
solubility: Aqueous Acid (Sparingly), Water (Slightly, Sonicated)
pka: 2.17 · 2.17(at 20℃)
form: Solid
color: White to Off-White
optical activity: 20 · [α]20/D 35°, c = 5 in 5 M HCl
Merck: 13 · 13,842
BRN: 1723526 · 1723526
Stability: Hygroscopic
Major Application: peptide synthesis
InChI: 1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1
InChIKey: DCXYFEDJOCDNAF-UWTATZPHSA-N
SMILES: N[C@H](CC(N)=O)C(O)=O
LogP: -1.88 · -1.880 (est)
CAS DataBase Reference: 2058 · 2058-58-4(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 6 QV1010K6 · T6QV1010K6
UNSPSC Code: 12352209 · 12352209
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 1 · 1
HS Code: 29241900 · 29241900
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 1
hs_code: 29241900
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Applications · 1 item

UsesD-Asparagine is an isomer of L-Asparagine (A790005) and is used by bacteria (such as Saccharomyces cerevisiae) as a sole nitrogen source for replication. L-Asparagine is also a competitive inhibitor of staphylococcal L-asparaginase and is used as a reagent to synthesize peptide antibiotics.