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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: (R)-lactate

Synonyms: (R)-2-hydroxypropanate, D-lactate

Superclasses: an acid all carboxy acids a carboxylate a hydroxy carboxylate a 2-hydroxy carboxylate lactate

Summary:
Lactate, or 2-hydroxypropanoate, was discovered in 1780 by a Swedish chemist, Scheele, who isolated it from sour milk. It is the simplest hydroxycarboxylic acid and exists as 2 stereoisomers. Lactate has a pK of 3.86 and dissociates freely at physiological pH, yielding a lactate ion:lactic acid ratio of 3000:1[Ewaschuk05].

Chemical Formula: C3H5O3

Molecular Weight: 89.071 Daltons

Monoisotopic Molecular Weight: 90.0316940589 Daltons

SMILES: CC(C([O-])=O)O

InChI: InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/p-1/t2-/m1/s1

InChIKey: InChIKey=JVTAAEKCZFNVCJ-UWTATZPHSA-M

Unification Links: CAS:10326-41-7 , ChEBI:16004 , ChemSpider:4573814 , HMDB:HMDB01311 , IAF1260:34414 , KEGG:C00256 , MetaboLights:MTBLC16004 , PubChem:5460179

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -72.12645 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2-chloroacrylate degradation I , D-lactate to cytochrome bo oxidase electron transport , methylglyoxal degradation I , methylglyoxal degradation II :
(R)-lactate + an ubiquinone[inner membrane] → pyruvate + an ubiquinol[inner membrane]

methylglyoxal degradation VI :
(R)-lactate + 2 an oxidized c-type cytochrome → pyruvate + 2 a reduced c-type cytochrome + 2 H+

vancomycin resistance I :
D-alanine + (R)-lactate + ATP → D-alanyl-D-lactate + ADP + phosphate

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

2-chloroacrylate degradation I :
(S)-2-chloropropanoate + H2O → (R)-lactate + chloride + H+

alanine degradation II (to D-lactate) , heterolactic fermentation , mixed acid fermentation , superpathway of fermentation (Chlamydomonas reinhardtii) , superpathway of glucose and xylose degradation , vancomycin resistance I :
(R)-lactate + NAD+ ↔ pyruvate + NADH + H+

methylglyoxal degradation I :
(R)-S-lactoylglutathione + H2O ↔ glutathione + (R)-lactate + H+

methylglyoxal degradation II :
(R)-lactate + H+ ← methylglyoxal + H2O

methylglyoxal degradation VI :
(R)-lactaldehyde + NAD+ + H2O → (R)-lactate + NADH + 2 H+

Not in pathways:
S-(2-hydroxyacyl)glutathione + H2O → glutathione + a 2-hydroxy carboxylate

3,3'-thiodipropionate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropionate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+


an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

1,2-propanediol biosynthesis from lactate (engineered) :
acetyl-CoA + (R)-lactate ↔ acetate + (R)-lactoyl-CoA

anhydromuropeptides recycling :
N-acetyl-β-muramate 6-phosphate + H2O ↔ N-acetyl-D-glucosamine 6-phosphate + (R)-lactate

pyruvate fermentation to propionate II (acrylate pathway) :
propanoyl-CoA + (R)-lactate ↔ propanoate + (R)-lactoyl-CoA

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
(S)-lactate = (R)-lactate
(R)-lactate + 2 an oxidized cytochrome c-553 = pyruvate + 2 a reduced cytochrome c-553 + 2 H+
(R)-lactate + an oxidized electron acceptor = pyruvate + a reduced electron acceptor


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized electron acceptor + H2O = a carboxylate + a reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

In Transport reactions:
(R)-lactate[periplasmic space] + H+[periplasmic space](R)-lactate[cytosol] + H+[cytosol] ,
lactate[cytosol]lactate[periplasmic space]

In Redox half-reactions:
pyruvate[in] + 2 H+[in] + 2 e-(R)-lactate[in]

Enzymes inhibited by (R)-lactate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: proline dehydrogenase [Scarpulla78]

Credits:
Revised 11-Sep-2009 by Caspi R , SRI International


References

Ewaschuk05: Ewaschuk JB, Naylor JM, Zello GA (2005). "D-lactate in human and ruminant metabolism." J Nutr 135(7);1619-25. PMID: 15987839

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Scarpulla78: Scarpulla RC, Soffer RL (1978). "Membrane-bound proline dehydrogenase from Escherichia coli. Solubilization, purification, and characterization." J Biol Chem 1978;253(17);5997-6001. PMID: 355248


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 21, 2014, biocyc14.