RefMet Compound Details

RefMet ID, RefMet name, exact mass and formula
RefMet ID	RM0135894
RefMet name	Malic acid
Systematic name	(2S)-2-hydroxybutanedioic acid
Synonyms	PubChem Synonyms
Exact mass	134.021525 (neutral)	Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M+2K-H]+ [M+Na]+ [M+2Na]2+ [M+2Na-H]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M.CH3]+ [M+Ag]+ [M+H+CH3OH]+ [M+H+CH3CN]+ [M+H+2CH3CN]+ [M+Na+CH3CN]+ [M.NaFormate+H]+ [M.NH4Formate+H]+ [M.TMSi]+ [M.tBuDMSi]+ [M+H-Hexose]+ [M+H-EtnP]+ [M+H-SerP]+ [M-H]- [M-H-H2O]- [M-CH3]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+Na-2H]- [M+K-2H]- [M.Formate]- [M.NaFormate-H]- [M.NH4Formate-H]- [M.F]- [M-H-Ser]- [M.HF2]- M(neutral)    View other RefMet entries with this exact (neutral) mass:   +/- 0.05 amu   +/- 0.1 amu   +/- 0.2 amu   +/- 0.5 amu
Formula	C4H6O5	View other entries in RefMet with this formula
Molecular descriptors
Molfile	37105 (Download molfile/View MW Metabolite Database details)
InChI	InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChIKey	BJEPYKJPYRNKOW-REOHCLBHSA-N	View other enantiomers/diastereomers of this metabolite in RefMet
SMILES	C([C@@H](C(=O)O)O)C(=O)O Run Tanimoto similarity search (with similarity coefficient >=0.6)
Chemical/Biochemical Classification
Super Class	Organic acids
Main Class	TCA acids
Sub Class	TCA acids
Distribution of Malic acid in NMDR studies
Species	Plot Species distribution
Sample source	Plot Sample source(tissue) distribution
Studies	NMDR Studies reporting Malic acid
External Links
Pubchem CID	222656
ChEBI ID	30797
KEGG ID	C00149
HMDB ID	HMDB0000156
Chemspider ID	193317
MetaCyc ID	MAL
Spectral data for Malic acid standards
BMRB ID(NMR)	View NMR spectra
NP-MRD ID(NMR)	View NMR spectra
MassBank(EU)	View MS spectra
Structural annotation level
Annotation level	1   (1:Known structure; 2:Known regiochemistry; 3:Partial structure; 4:Sum-composition)

Table of KEGG reactions in human pathways involving Malic acid

Rxn ID	KEGG Reaction	Enzyme
R00214	(S)-Malate + NAD+ <=> Pyruvate + CO2 + NADH + H+	(S)-malate:NAD+ oxidoreductase (decarboxylating)
R00216	(S)-Malate + NADP+ <=> Pyruvate + CO2 + NADPH + H+	(S)-Malate:NADP+ oxidoreductase(oxaloacetate-decarboxylating)
R00342	(S)-Malate + NAD+ <=> Oxaloacetate + NADH + H+	(S)-malate:NAD+ oxidoreductase
R00343	(S)-Malate + NADP+ <=> Oxaloacetate + NADPH + H+	(S)-malate:NADP+ oxidoreductase
R00361	(S)-Malate + Quinone <=> Oxaloacetate + Hydroquinone	(S)-malate:quinone oxidoreductase
R01082	(S)-Malate <=> Fumarate + H2O	(S)-malate hydro-lyase (fumarate-forming)

Table of KEGG human pathways containing Malic acid

Pathway ID	Human Pathway	# of reactions
hsa00620	Pyruvate metabolism	4
hsa00020	Citrate cycle (TCA cycle)	2
hsa01100	Metabolic pathways	2
hsa01200	Carbon metabolism	2
hsa00630	Glyoxylate and dicarboxylate metabolism	1