(R)-malic acid (CHEBI:30796)

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CHEBI:30796 - (R)-malic acid

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ChEBI Name	(R)-malic acid

ChEBI ID	CHEBI:30796

ChEBI ASCII Name	(R)-malic acid

Definition	An optically active form of malic acid having (R)-configuration.

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

Secondary ChEBI IDs	CHEBI:44073, CHEBI:42060, CHEBI:342, CHEBI:18686

Supplier Information	ChemicalBook:CB9373789, eMolecules:475035, ZINC000000895264

Download	Molfile XML SDF

more structures >>

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Marvin 03281114233D

15 14 0 0 0 0 999 V2000

-1.3991 -0.5668 -1.2693 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0519 -0.5718 -0.7367 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5199 0.4463 0.9194 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1608 0.4491 0.4140 C 0 0 2 0 0 0 0 0 0 0 0 0

2.2448 1.4297 0.8387 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1262 -1.5487 -1.1946 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9978 -0.5492 1.4465 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.8602 0.4297 -1.8080 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.7403 0.1782 1.4881 O 0 0 0 0 0 0 0 0 0 0 0 0

0.1988 -1.5735 -0.3725 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6382 -0.3575 -1.5582 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0881 1.4483 0.0403 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9523 2.1713 0.4647 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8385 -2.2865 -0.8093 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6084 0.9013 2.1369 H 0 0 0 0 0 0 0 0 0 0 0 0

8 1 2 0 0 0 0

1 2 1 0 0 0 0

7 3 2 0 0 0 0

4 2 1 0 0 0 0

4 3 1 0 0 0 0

4 9 1 0 0 0 0

5 3 1 0 0 0 0

6 1 1 0 0 0 0

2 10 1 0 0 0 0

2 11 1 0 0 0 0

4 12 1 0 0 0 0

5 13 1 0 0 0 0

6 14 1 0 0 0 0

9 15 1 0 0 0 0

M END): 22 ms

reading 15 atoms

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Wikipedia	License
Malic acid is an organic compound with the molecular formula HO2CCH(OH)CH2CO2H. It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is a metabolic intermediate in the citric acid cycle.
Read full article at Wikipedia

Formula

C4H6O5

Net Charge

Average Mass

134.08740

Monoisotopic Mass

134.02152

InChI

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1

InChIKey

BJEPYKJPYRNKOW-UWTATZPHSA-N

SMILES

O[C@H](CC(O)=O)C(O)=O

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

Biological Role(s):	fundamental metabolite Any metabolite produced by all living cells. (via malic acid ) food acidity regulator A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents. (via malic acid )

Application(s):	food acidity regulator A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents. (via malic acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(R)-malic acid (CHEBI:30796) is a malic acid (CHEBI:6650) (R)-malic acid (CHEBI:30796) is conjugate acid of (R)-malate(2−) (CHEBI:15588) (R)-malic acid (CHEBI:30796) is enantiomer of (S)-malic acid (CHEBI:30797)

Incoming	(3R)-3-carboxy-3-hydroxypropanoyl-CoA (CHEBI:77653) has functional parent (R)-malic acid (CHEBI:30796) (R)-malate(2−) (CHEBI:15588) is conjugate base of (R)-malic acid (CHEBI:30796) (S)-malic acid (CHEBI:30797) is enantiomer of (R)-malic acid (CHEBI:30796)

IUPAC Name

(2R)-2-hydroxybutanedioic acid

Synonyms	Sources
(+)-D-malic acid	ChEBI
(R)-2-hydroxybutanedioic acid	ChEBI
2-HYDROXY-SUCCINIC ACID	PDBeChem
D-Malic acid	KEGG COMPOUND
D-malic acid	ChEBI

Manual Xrefs	Databases
C00497	KEGG COMPOUND
CPD-660	MetaCyc
HMDB0000744	HMDB
Malic_acid	Wikipedia
MLT	PDBeChem
View more database links

Registry Numbers	Types	Sources
1723540	Reaxys Registry Number	Reaxys
636-61-3	CAS Registry Number	KEGG COMPOUND
636-61-3	CAS Registry Number	ChemIDplus
636-61-3	CAS Registry Number	NIST Chemistry WebBook

Citations

Bordbar A, Mo ML, Nakayasu ES, Schrimpe-Rutledge AC, Kim YM, Metz TO, Jones MB, Frank BC, Smith RD, Peterson SN, Hyduke DR, Adkins JN, Palsson BO (2012)
Model-driven multi-omic data analysis elucidates metabolic immunomodulators of macrophage activation.
Molecular systems biology 8, 558 [PubMed:22735334]
[show Abstract]

Eisele TA (1996)
Determination of D-malic acid in apple juice by liquid chromatography: collaborative study.
Journal of AOAC International 79, 50-54 [PubMed:8620111]
[show Abstract]

VISHWAKARMA P, LOTSPEICH WD (1960)
Excretion of D-malic acid in the chicken.
The American journal of physiology 198, 824-828 [PubMed:13842473]

Last Modified

20 November 2019

CHEBI:30796 - (R)-malic acid

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