D-arginine (CHEBI:15816)

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CHEBI:15816 - D-arginine

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ChEBI Name	D-arginine

ChEBI ID	CHEBI:15816

ChEBI ASCII Name	D-arginine

Definition	A D-α-amino acid that is the D-isomer of arginine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41855, CHEBI:4106, CHEBI:12917, CHEBI:20917

Supplier Information	ChemicalBook:CB2408147, eMolecules:478564, ZINC000001532749

Download	Molfile XML SDF

more structures >>

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Marvin 06261213483D

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Marvin 06261213483D

27 26 0 0 0 0 999 V2000

-2.3180 1.7860 -0.3080 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.2600 0.4860 0.3730 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.0230 -0.2820 -0.0990 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2380 0.4630 0.3420 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4750 -0.3050 -0.1300 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6830 0.4090 0.2920 N 0 0 0 0 0 0 0 0 0 0 0 0

3.9170 -0.0930 -0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0

4.0200 -1.2290 -0.7050 N 0 0 0 0 0 0 0 0 0 0 0 0

5.0150 0.5560 0.3650 N 0 3 0 0 0 0 0 0 0 0 0 0

-3.4990 -0.3080 0.0470 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.8700 -1.3270 0.8380 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.1570 -0.0280 -0.9260 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.3710 1.5930 -1.2970 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1960 2.2100 -0.0480 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2010 0.6420 1.4500 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6080 1.2360 0.7930 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.8332 -1.6490 0.6794 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0270 -1.2810 0.3380 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0370 -0.3610 -1.1860 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2420 1.4620 -0.0950 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2530 0.5420 1.4290 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4710 -1.3030 0.3070 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4610 -0.3830 -1.2170 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2210 -1.7010 -0.9850 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8960 -1.5840 -0.9260 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8900 0.2000 0.1450 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9400 1.3840 0.8650 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 13 1 0 0 0 0

1 14 1 0 0 0 0

2 3 1 0 0 0 0

2 10 1 0 0 0 0

2 15 1 0 0 0 0

3 4 1 0 0 0 0

3 18 1 0 0 0 0

3 19 1 0 0 0 0

4 5 1 0 0 0 0

4 20 1 0 0 0 0

4 21 1 0 0 0 0

5 6 1 0 0 0 0

5 22 1 0 0 0 0

5 23 1 0 0 0 0

6 7 1 0 0 0 0

6 16 1 0 0 0 0

7 8 1 0 0 0 0

7 9 2 0 0 0 0

8 24 1 0 0 0 0

8 25 1 0 0 0 0

9 26 1 0 0 0 0

9 27 1 0 0 0 0

10 11 2 0 0 0 0

10 12 1 0 0 0 0

12 17 1 0 0 0 0

M CHG 1 9 1

M END): 16 ms

reading 27 atoms

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27 atoms created

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Formula

C6H14N4O2

Net Charge

Average Mass

174.20100

Monoisotopic Mass

174.11168

InChI

InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1

InChIKey

ODKSFYDXXFIFQN-SCSAIBSYSA-N

SMILES

N[C@H](CCCNC(N)=N)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). EC 4.1.1.19 (arginine decarboxylase) inhibitor An EC 4.1.1.* (carboxy-lyase) inhibitor that interferes with the action of arginine decarboxylase (EC 4.1.1.19). fundamental metabolite Any metabolite produced by all living cells. (via arginine )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	D-arginine (CHEBI:15816) has role EC 4.1.1.19 (arginine decarboxylase) inhibitor (CHEBI:65053) D-arginine (CHEBI:15816) has role mouse metabolite (CHEBI:75771) D-arginine (CHEBI:15816) is a D-α-amino acid (CHEBI:16733) D-arginine (CHEBI:15816) is a arginine (CHEBI:29016) D-arginine (CHEBI:15816) is conjugate acid of D-argininate (CHEBI:32688) D-arginine (CHEBI:15816) is conjugate base of D-argininium(1+) (CHEBI:32689) D-arginine (CHEBI:15816) is enantiomer of L-arginine (CHEBI:16467)

Incoming	D-arginine derivative (CHEBI:83966) has functional parent D-arginine (CHEBI:15816) vanchrobactin (CHEBI:157682) has functional parent D-arginine (CHEBI:15816) D-argininium(1+) (CHEBI:32689) is conjugate acid of D-arginine (CHEBI:15816) D-argininate (CHEBI:32688) is conjugate base of D-arginine (CHEBI:15816) L-arginine (CHEBI:16467) is enantiomer of D-arginine (CHEBI:15816) N^ω-D-arginino group (CHEBI:32694) is substituent group from D-arginine (CHEBI:15816) N²-D-arginino group (CHEBI:32693) is substituent group from D-arginine (CHEBI:15816) D-arginine residue (CHEBI:29953) is substituent group from D-arginine (CHEBI:15816) D-arginyl group (CHEBI:32691) is substituent group from D-arginine (CHEBI:15816)

IUPAC Name

D-arginine

Synonyms	Sources
(2R)-2-amino-5-(carbamimidamido)pentanoic acid	IUPAC
(2R)-2-amino-5-guanidinopentanoic acid	JCBN
(R)-2-amino-5-guanidinopentanoic acid	ChEBI
D-2-Amino-5-guanidinovaleric acid	KEGG COMPOUND
D-Arginin	ChEBI
D-Arginine	KEGG COMPOUND
DAR	PDBeChem

Manual Xrefs	Databases
C00792	KEGG COMPOUND
CPD-220	MetaCyc
DAR	PDBeChem
DB04027	DrugBank
HMDB0003416	HMDB
View more database links

Registry Numbers	Types	Sources
157-06-2	CAS Registry Number	KEGG COMPOUND
157-06-2	CAS Registry Number	ChemIDplus
157-06-2	CAS Registry Number	NIST Chemistry WebBook
1725412	Reaxys Registry Number	Reaxys
364938	Gmelin Registry Number	Gmelin

Citations

Dhar I, Dhar A, Wu L, Desai K (2012)
Arginine attenuates methylglyoxal- and high glucose-induced endothelial dysfunction and oxidative stress by an endothelial nitric-oxide synthase-independent mechanism.
The Journal of pharmacology and experimental therapeutics 342, 196-204 [PubMed:22518022]
[show Abstract]

Huang X, Bie Z (2010)
Cinnamic acid-inhibited ribulose-1,5-bisphosphate carboxylase activity is mediated through decreased spermine and changes in the ratio of polyamines in cowpea.
Journal of plant physiology 167, 47-53 [PubMed:19651461]
[show Abstract]

Liu JH, Moriguchi T (2007)
Changes in free polyamine titers and expression of polyamine biosynthetic genes during growth of peach in vitro callus.
Plant cell reports 26, 125-131 [PubMed:16912865]
[show Abstract]

Hao YJ, Kitashiba H, Honda C, Nada K, Moriguchi T (2005)
Expression of arginine decarboxylase and ornithine decarboxylase genes in apple cells and stressed shoots.
Journal of experimental botany 56, 1105-1115 [PubMed:15723827]
[show Abstract]

Brown AE, Grossman SH (2004)
The mechanism and modes of inhibition of arginine kinase from the cockroach (Periplaneta americana).
Archives of insect biochemistry and physiology 57, 166-177 [PubMed:15540275]
[show Abstract]
The kinetic mechanism and evaluation of several potential inhibitors of purified arginine kinase from the cockroach (Periplanta americana) were investigated. This monomeric phosphagen kinase is important in maintaining ATP levels during the rapid energy demands of muscle required for contraction and motility. Analysis reveals the following dissociation constants (mM) for the binary complex: E.Arg P-->E+Arg P, K=1.0; E.Arg-->E+Arg, K=0.45; E.MgATP-->E+MgATP, K=0.17; E.MgADP-->E+MgADP, K=0.12; and the ternary complex: Arg P.E.MgADP-->E.MgADP+Arg P, K=0.94; Arg.E.MgATP-->E.MgATP+Arg, K=0.49; MgATP.Enz.Arg-->E.Arg+MgATP, K=0.14; MgADP.E.Arg P-->E.Arg P+MgADP, K=0.09. For a particular substrate, the ratio of the dissociation constants for the binary to ternary complex is close to one, indicating little, if any, cooperativity in substrate binding for the rapid equilibrium, random addition mechanism. The time course of the arginine kinase reaction exhibits a pronounced curvature, which, as described for enzyme from other sources, is attributed to formation of an inhibitory catalytic dead-end complex, MgADP.E.Arg. The curvature is accentuated by the addition of monovalent anions, including borate, thiocyanate, and, most notably, nitrite and nitrate. This effect is attributed to stabilization of the dead-end complex through formation of a transition state analog. However, the substantial decrease in initial velocity (92%) caused by nitrate is due to an additional inhibitory effect, further characterized as non-competitive inhibition (Ki=8.0 mM) with the substrate L-arginine. On the other hand, borate inhibition of the initial velocity is only 30% with significant subsequent curvature, suggesting that this anion functions as an inhibitor mainly by formation of a transition state analog. However, some component of the borate inhibition appears to be mediated by an apparent partial competitive inhibition with L-arginine. D-arginine is not a substrate for arginine kinase from the cockroach, but is an effective competitive inhibitor with a Ki=0.31 mM. L-Canavanine is a weak substrate for arginine kinase (Km=6.7 mM) with a Vmax for the pure enzyme that is approximately one-third that of L-arginine. However, initial velocity experiments of substrate mixtures suggest that competition between L-canavanine and L-arginine may not be a simple summation effect and may involve a structural modification. Sensitivity of arginine kinase activity to D-arginine as well as nitrate and borate anions, coupled with the fact that L-arginine is an essential amino acid for the cockroach, suggest that arginine kinase could be a useful chemotherapeutic target for the control of cockroach proliferation.

Last Modified

25 January 2021

CHEBI:15816 - D-arginine

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