D-threo-isocitric acid (CHEBI:151)

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CHEBI:151 - D-threo-isocitric acid

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ChEBI Name	*D-threo-isocitric acid*

ChEBI ID	CHEBI:151

ChEBI ASCII Name	D-threo-isocitric acid

Definition	The D-threo-diastereomer of isocitric acid.

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

Supplier Information	ZINC000000895179

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

Marvin 11300713493D

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Marvin 11300713493D

21 20 0 0 1 0 999 V2000

1.0278 -3.0102 1.2149 O 0 0 0 0 0 0 0 0 0 0 0 0

0.7236 -1.8569 1.4913 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3835 -0.0594 0.0712 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.1214 1.1469 -0.8878 C 0 0 2 0 0 0 0 0 0 0 0 0

0.9238 -0.7725 0.5508 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7427 2.1697 -0.3222 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3026 3.0543 0.4022 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.3085 -1.0216 -0.5242 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3587 1.7460 -1.2853 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.3940 -1.2688 -0.0108 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.0241 -1.6306 -1.5466 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9494 2.1519 -0.5203 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2298 -1.6512 2.5899 O 0 0 0 0 0 0 0 0 0 0 0 0

1.3748 -3.2010 0.4285 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8565 0.3635 0.9663 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3335 0.7771 -1.8129 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5855 -0.0609 1.0509 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4743 -1.1246 -0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8394 3.6569 0.7548 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1238 2.4568 -1.9179 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9366 -1.8653 -0.3652 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 1 0 0 0 0

2 13 2 0 0 0 0

3 8 1 0 0 0 0

3 4 1 0 0 0 0

4 9 1 0 0 0 0

5 2 1 0 0 0 0

3 5 1 0 0 0 0

4 6 1 0 0 0 0

6 12 2 0 0 0 0

6 7 1 0 0 0 0

8 10 1 0 0 0 0

8 11 2 0 0 0 0

1 14 1 0 0 0 0

3 15 1 0 0 0 0

4 16 1 0 0 0 0

5 17 1 0 0 0 0

5 18 1 0 0 0 0

7 19 1 0 0 0 0

9 20 1 0 0 0 0

10 21 1 0 0 0 0

M END): 18 ms

reading 21 atoms

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1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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21 atoms created

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Formula

C6H8O7

Net Charge

Average Mass

192.12352

Monoisotopic Mass

192.02700

InChI

InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4+/m0/s1

InChIKey

ODBLHEXUDAPZAU-ZAFYKAAXSA-N

SMILES

O[C@H]([C@H](CC(O)=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):	fundamental metabolite Any metabolite produced by all living cells. (via isocitric acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	D-threo-isocitric acid (CHEBI:151) is a isocitric acid (CHEBI:30887) D-threo-isocitric acid (CHEBI:151) is conjugate acid of D-threo-isocitrate(3−) (CHEBI:15562) D-threo-isocitric acid (CHEBI:151) is enantiomer of L-threo-isocitric acid (CHEBI:30889)

Incoming	D-threo-isocitrate(3−) (CHEBI:15562) is conjugate base of D-threo-isocitric acid (CHEBI:151) L-threo-isocitric acid (CHEBI:30889) is enantiomer of D-threo-isocitric acid (CHEBI:151)

IUPAC Names

(1R,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid

3-carboxy-2,3-dideoxy-L-threo-pentaric acid

Synonyms	Sources
(+)-threo-isocitric acid	HMDB
D-threo-Isocitric acid	KEGG COMPOUND
ISOCITRIC ACID	PDBeChem

Manual Xrefs	Databases
C00001188	KNApSAcK
C00451	KEGG COMPOUND
HMDB0001874	HMDB
ICT	PDBeChem
THREO-DS-ISO-CITRATE	MetaCyc
View more database links

Registry Numbers	Types	Sources
1220309	Gmelin Registry Number	Gmelin
1727947	Reaxys Registry Number	Reaxys
6061-97-8	CAS Registry Number	KEGG COMPOUND

Citation

Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG (2007)
Growth control of the eukaryote cell: a systems biology study in yeast.
Journal of biology 6, 4 [PubMed:17439666]
[show Abstract]

Background

Cell growth underlies many key cellular and developmental processes, yet a limited number of studies have been carried out on cell-growth regulation. Comprehensive studies at the transcriptional, proteomic and metabolic levels under defined controlled conditions are currently lacking.

Results

Metabolic control analysis is being exploited in a systems biology study of the eukaryotic cell. Using chemostat culture, we have measured the impact of changes in flux (growth rate) on the transcriptome, proteome, endometabolome and exometabolome of the yeast Saccharomyces cerevisiae. Each functional genomic level shows clear growth-rate-associated trends and discriminates between carbon-sufficient and carbon-limited conditions. Genes consistently and significantly upregulated with increasing growth rate are frequently essential and encode evolutionarily conserved proteins of known function that participate in many protein-protein interactions. In contrast, more unknown, and fewer essential, genes are downregulated with increasing growth rate; their protein products rarely interact with one another. A large proportion of yeast genes under positive growth-rate control share orthologs with other eukaryotes, including humans. Significantly, transcription of genes encoding components of the TOR complex (a major controller of eukaryotic cell growth) is not subject to growth-rate regulation. Moreover, integrative studies reveal the extent and importance of post-transcriptional control, patterns of control of metabolic fluxes at the level of enzyme synthesis, and the relevance of specific enzymatic reactions in the control of metabolic fluxes during cell growth.

Conclusion

This work constitutes a first comprehensive systems biology study on growth-rate control in the eukaryotic cell. The results have direct implications for advanced studies on cell growth, in vivo regulation of metabolic fluxes for comprehensive metabolic engineering, and for the design of genome-scale systems biology models of the eukaryotic cell.

Last Modified

17 July 2014

CHEBI:151 - D-threo-isocitric acid

Background

Results

Conclusion

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