(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:CB2177472, eMolecules:712832, eMolecules:27520527, eMolecules:518165

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): 20 ms

reading 15 atoms

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15 atoms created

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Wikipedia	License
Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adults also. It is encoded by the codons CAU and CAC. Histidine was first isolated by Albrecht Kossel and Sven Gustaf Hedin in 1896. The name stems from its discovery in tissue, from ἱστός histós "tissue". It is also a precursor to histamine, a vital inflammatory agent in immune responses. The acyl radical is histidyl.
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	Types	Sources
13842473	PubMed citation	Europe PMC
22735334	PubMed citation	Europe PMC
8620111	PubMed citation	Europe PMC

Last Modified

20 November 2019

CHEBI:30796 - (R)-malic acid

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