meso-tartaric acid (CHEBI:15673)

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CHEBI:15673 - meso-tartaric acid

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ChEBI Name	meso-tartaric acid

ChEBI ID	CHEBI:15673

ChEBI ASCII Name	meso-tartaric acid

Definition	A 2,3-dihydroxybutanedioic acid that has meso configuration.

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

Secondary ChEBI IDs	CHEBI:25206, CHEBI:45680, CHEBI:10599

Supplier Information	ChemicalBook:CB1257009, eMolecules:30316209, ZINC000000895297

Download	Molfile XML SDF

more structures >>

Molfile

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Marvin 03190823353D

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Marvin 03190823353D

16 15 0 0 0 0 999 V2000

1.8745 1.3483 1.3229 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2052 2.6867 0.7678 O 0 0 0 0 0 0 0 0 0 0 0 0

0.6167 1.5586 0.9020 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2808 0.3883 0.5963 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.5911 0.8621 0.2819 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2808 -0.3883 -0.5963 C 0 0 1 0 0 0 0 0 0 0 0 0

1.5911 -0.8621 -0.2819 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.6167 -1.5586 -0.9020 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2052 -2.6867 -0.7678 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.8745 -1.3483 -1.3229 O 0 0 0 0 0 0 0 0 0 0 0 0

2.4505 2.1004 1.5196 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3305 -0.2676 1.4655 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5029 1.4377 -0.4901 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3305 0.2676 -1.4655 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5029 -1.4377 0.4901 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4505 -2.1004 -1.5196 H 0 0 0 0 0 0 0 0 0 0 0 0

1 3 1 0 0 0 0

1 11 1 0 0 0 0

2 3 2 0 0 0 0

3 4 1 0 0 0 0

4 5 1 0 0 0 0

4 6 1 0 0 0 0

4 12 1 0 0 0 0

5 13 1 0 0 0 0

6 7 1 0 0 0 0

6 8 1 0 0 0 0

6 14 1 0 0 0 0

7 15 1 0 0 0 0

8 9 2 0 0 0 0

8 10 1 0 0 0 0

10 16 1 0 0 0 0

M END): 18 ms

reading 16 atoms

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16 atoms created

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Molfile expand

Formula

C4H6O6

Net Charge

Average Mass

150.08684

Monoisotopic Mass

150.01644

InChI

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2+

InChIKey

FEWJPZIEWOKRBE-XIXRPRMCSA-N

SMILES

O[C@@H]([C@@H](O)C(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):	human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. (via 2,3-dihydroxybutanedioic acid ) plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via 2,3-dihydroxybutanedioic acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	meso-tartaric acid (CHEBI:15673) is a 2,3-dihydroxybutanedioic acid (CHEBI:15674) meso-tartaric acid (CHEBI:15673) is conjugate acid of meso-tartrate(1−) (CHEBI:35400)

Incoming	(2R,3S)-cis-coutaric acid (CHEBI:76096) has functional parent meso-tartaric acid (CHEBI:15673) (2R,3S)-trans-coutaric acid (CHEBI:76095) has functional parent meso-tartaric acid (CHEBI:15673) (2S,3R)-cis-caftaric acid (CHEBI:76082) has functional parent meso-tartaric acid (CHEBI:15673) (2S,3R)-trans-caftaric acid (CHEBI:76075) has functional parent meso-tartaric acid (CHEBI:15673) meso-tartrate(1−) (CHEBI:35400) is conjugate base of meso-tartaric acid (CHEBI:15673)

IUPAC Name

(2R,3S)-2,3-dihydroxybutanedioic acid

Synonyms	Sources
(2R,3S)-2,3-dihydroxysuccinic acid	ChEBI
(2R,3S)-rel-2,3-dihydroxybutanedioic acid	ChemIDplus
(2R,3S)-tartaric acid	IUPAC
(R,S)-2,3-dihydroxybutanedioic acid	ChemIDplus
erythraric acid	IUPAC
i-tartaric acid	ChEBI
internally compensated tartaric acid	NIST Chemistry WebBook
m-tartaric acid	ChEBI
meso-Tartaric acid	KEGG COMPOUND
meso-tartaric acid	IUPAC
mesotartaric acid	ChemIDplus
Mesoweinsäure	ChEBI
S,R MESO-TARTARIC ACID	PDBeChem
unresolvable tartaric acid	NIST Chemistry WebBook

Manual Xrefs	Databases
C00552	KEGG COMPOUND
DB14756	DrugBank
MX2011012689	Patent
SRT	PDBeChem
View more database links

Registry Numbers	Types	Sources
147-73-9	CAS Registry Number	KEGG COMPOUND
147-73-9	CAS Registry Number	ChemIDplus
147-73-9	CAS Registry Number	NIST Chemistry WebBook
1725146	Beilstein Registry Number	Beilstein
3214	Gmelin Registry Number	Gmelin
4666811	Beilstein Registry Number	Beilstein

Citations

Liao H, Pan H, Yao J, Zhu R, Bao W (2024)
Essential amino acid residues and catalytic mechanism of trans-epoxysuccinate hydrolase for production of meso-tartaric acid.
Biotechnology letters 46, 739-749 [PubMed:38740717]
[show Abstract]

Rychlewska U, Waścinska N, Warzajtis B, Gawroński J (2008)
Role of the gauche effect and local 1,3-dipole-dipole interactions in stabilizing an unusual conformation of tartarodinitriles.
Acta crystallographica. Section B, Structural science 64, 497-503 [PubMed:18641452]
[show Abstract]

Widmer R, Haug FJ, Ruffieux P, Gröning O, Bielmann M, Gröning P, Fasel R (2006)
Surface chirality of CuO thin films.
Journal of the American Chemical Society 128, 14103-14108 [PubMed:17061893]
[show Abstract]

Jahn M, Baynes JW, Spiteller G (1999)
The reaction of hyaluronic acid and its monomers, glucuronic acid and N-acetylglucosamine, with reactive oxygen species.
Carbohydrate research 321, 228-234 [PubMed:10614067]
[show Abstract]

Last Modified

28 November 2024

ChEBI

CHEBI:15673 - meso-tartaric acid

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