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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
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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 Dec 19, 2014, BIOCYC14B.