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Details

Stereochemistry EPIMERIC
Molecular Formula C6H13N3O3.C4H6O5
Molecular Weight 309.2732
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CITRULLINE MALATE

SMILES

OC(CC(O)=O)C(O)=O.N[C@@H](CCCNC(N)=O)C(O)=O

InChI

InChIKey=DROVUXYZTXCEBX-WCCKRBBISA-N
InChI=1S/C6H13N3O3.C4H6O5/c7-4(5(10)11)2-1-3-9-6(8)12;5-2(4(8)9)1-3(6)7/h4H,1-3,7H2,(H,10,11)(H3,8,9,12);2,5H,1H2,(H,6,7)(H,8,9)/t4-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C6H13N3O3
Molecular Weight 175.1857
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Citrulline malate (CM) is an organic salt made up of the non-essential amino acid L-citrulline and L-malic acid, an intermediate in the citric acid cycle. The main dietary source of citrulline is watermelon (Citrullus vulgaris), while malic acid is common to apples (Malus pumila) and grapes (Vitis vinifera). Initially, Citrulline malate was utilized as a pharmaceutical drug (STIMOL©, BIOCODEX Gentilly, France), for the treatment of patients suffering from asthenia to mitigate recovery time following physical activity. Citrulline malate has been purported to improve performance in both aerobic and anaerobic exercise modalities via a variety of mechanisms including improved ammonia and lactic acid metabolism, increased oxygen delivery capacity via increased vasodilation and increased adenosine triphosphate production via increases in Krebs cycle intermediates. Citrulline malate has been shown to increase lactate and ammonia clearance following exercise; this is via acting as a nitrogen ion acceptor during the first stage of the urea cycle. Supplementation may, therefore, improve ammonia-buffering capabilities reducing acidosis which occurs during intense exercise, as well as reducing muscle soreness post-exercise.

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 02:03:15 GMT 2023
Edited
by admin
on Sat Dec 16 02:03:15 GMT 2023
Record UNII
PAB4036KHO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CITRULLINE MALATE
WHO-DD  
Common Name English
Citrulline malate [WHO-DD]
Common Name English
CITRULLINE MALATE (SALT) [MI]
Common Name English
L-CITRULLINE DL-MALATE
Common Name English
L-ORNITHINE, N5-(AMINOCARBONYL)-, HYDROXYBUTANEDIOATE (1:1)
Common Name English
L-ORNITHINE, N5-(AMINOCARBONYL)-, 2-HYDROXYBUTANEDIOATE (1:1)
Common Name English
L-CITRULLINE MALATE
Common Name English
STIMOL
Brand Name English
Classification Tree Code System Code
DSLD 2471 (Number of products:683)
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
Code System Code Type Description
CAS
70796-17-7
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY
EVMPD
SUB13385MIG
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY
CAS
54940-97-5
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
SUPERSEDED
EPA CompTox
DTXSID60970275
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY
MESH
C071162
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY
CAS
62140-20-9
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
SUPERSEDED
SMS_ID
100000080115
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY
PUBCHEM
162762
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY
FDA UNII
PAB4036KHO
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY
MERCK INDEX
m3600
Created by admin on Sat Dec 16 02:03:15 GMT 2023 , Edited by admin on Sat Dec 16 02:03:15 GMT 2023
PRIMARY Merck Index