ChemicalBook CAS DataBase List 5302-45-4

5302-45-4

Name	3-N-OXALYL-L-2,3-DIAMINOPROPANOICACID
CAS	5302-45-4
Molecular Formula	C5H8N2O5
MDL Number	MFCD00055228
Molecular Weight	176.13
MOL File	5302-45-4.mol

Synonyms

ODAP BOAA β-ODAP 10-25Mg β-L-ODAP Dencichin L-Dencichin beta-ODAP >=98% (HPLC) β-N-Oxalylamino-L-alanine BETA-N-OXALAMINO-L-ALANINE BETA-N-OXYALYLAMINE-L-ALANINE DENCICHINE; L-DENCICHIN; ODAP N3-oxalyl-L-2,3-diaminopropionicaci 3-[(Carboxycarbonyl)amino]-L-alanine 3-N-OXALYL-L-2,3-DIAMINOPROPANOICACID L-Alanine, 3-[(carboxycarbonyl)amino]- N(3)-oxalyl-L-2,3-diaminopropionic acid BETA-N-OXALYL-ALPHA,BETA-DIAMINOPROPIONICACID (S)-2-AMino-3-(carboxyforMaMido)propanoic acid (S)-2-Amino-3-[(1,2-dioxo-2-hydroxyethyl)amino]propionic acid

Chemical Properties

density	1.596±0.06 g/cm3 (20 ºC 760 Torr)
storage temp.	Keep in dark place,Sealed in dry,2-8°C
solubility	0.1 M HCl: soluble2mg/mL, clear (warmed)
form	powder
pka	1.99±0.10(Predicted)
color	white to beige
Optical Rotation	[α]/D -17 to -23°, c = 0.5 (Solvent: 4N HCl)
InChI	InChI=1S/C5H8N2O5/c6-2(4(9)10)1-7-3(8)5(11)12/h2H,1,6H2,(H,7,8)(H,9,10)(H,11,12)/t2-/m0/s1
InChIKey	NEEQFPMRODQIKX-REOHCLBHSA-N
SMILES	C(O)(=O)[C@H](CNC(C(O)=O)=O)N

Safety Data

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

Colorless crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the dried roots of Panax notoginseng.

Uses

Dencichin is a non-protein amino acid originally extracted from Panax notoginseng, and can inhibit HIF-prolyl hydroxylase-2 (PHD-2) activity.

Definition

ChEBI: An Nbeta-acyl-L-2,3-diaminopropionic acid in which the acyl group is oxalyl.

Biological Activity

β-ODAP is a potent inhibitor of HIF-prolyl hydroxylase-2 (PHD-2) th at induces HIF dependent HRE (hypoxia response element) in normoxic conditions. β-ODAP is an analog of glutamic acid present in Lathyrus sativus (grass pea) th at activates AMPA receptors. β-ODAP causes neurolathyrism upon prolonged consumption of L. sativus seeds.''β-ODAP is considered more neurotoxic than α-ODAPthus during food processingits conversion to α isomer is essential. β-ODAP exhibits its neurotoxicity via the activation of metabotropic glutamatergic receptor.

in vivo

Dencichin improves metabolism disorder in diabetic nephropathy (DN) secondary to type II diabetes mellitus (DM) model. Dencichin (80, 160 mg/kg/day, p.o.) significantly prevents the up-regulation of TCH, TG, LDL, and HbAlc and the down-regulation of HDL in DN rats induced by STZ injection. Dencichin also attenuates renal injury induced in the DN secondary to type II DM model. Dencichin alleviates pancreas damage in the STZ-induced DN model. Dencichin regulates protein expression in the TGF-β/Smad signalling pathway in STZ-induced DN models^[2].

References

[1] Eslavath RK, et al. β-N-oxalyl-L-α, β- diaminopropionic acid induces HRE expression by inhibiting HIF-prolyl hydroxylase-2 in normoxic conditions. Eur J Pharmacol. 2016 Nov 15;791:405-411. DOI:10.1016/j.ejphar.2016.07.007
[2] Jie L, et al. Dencichine ameliorates kidney injury in induced type II diabetic nephropathy via the TGF-β/Smad signalling pathway. Eur J Pharmacol. 2017 Oct 5;812:196-205. DOI:10.1016/j.ejphar.2017.06.024

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