(S)-Malate (BioCAD00000000994)

blood cellular cytoplasm cerebrospinal fluid (csf) feces saliva sweat urine placenta prostate

Metabolite Card

Formula: C4H6O5 (134.0215)
SMILES: O[C@@H](CC(O)=O)C(O)=O

Synonyms [en]

L-Malic acid; (S)-malate; Malic acid; (S)-Malic acid; L-Apple acid; (-)-L-Malic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

(S)-Malate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000000994). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Malic acid (CAS: 6915-15-7) is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. Apples contain malic acid, which contributes to the sourness of a green apple. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness (Wikipedia). In its ionized form, malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. In humans, malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions, the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions, where a buildup of excess reducing equivalents inhibits glycolysis, malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats, it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this, a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably, the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production. Malic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 26999-59-7
  • CAS Registry Number: 6915-15-7
  • CAS Registry Number: 97-67-6
  • PubChem: 222656
  • PubChem: 3449
  • ChEBI: ChEBI:15589
  • ChEBI: ChEBI:30797
  • ChEBI: ChEBI:6650
  • HMDB: HMDB0000156
  • KEGG: C00149
  • BioCyc: MAL
  • Wikipedia: Malic acid
  • RefMet: RM0135894
  • MoNA: CCMSLIB00000578132
  • MoNA: EMBL-MCF_spec101927
  • MoNA: EMBL-MCF_spec27461
  • MoNA: EMBL_MCF_2_0_HRMS_Library000319
  • MoNA: FiehnHILIC001309
  • MoNA: FiehnHILIC002812
  • MoNA: FiehnLib001092
  • MoNA: HMDB0000156_ms_ms_239
  • MoNA: HMDB0000156_ms_ms_240
  • MoNA: HMDB0000156_ms_ms_241
  • MoNA: HMDB0000744_c_ms_1176
  • MoNA: HMDB0000744_ms_ms_1056
  • MoNA: HMDB0000744_ms_ms_1057
  • MoNA: HMDB0000744_ms_ms_1058
  • MoNA: KNA00527
  • MoNA: KNA00529
  • MoNA: KO001305
  • MoNA: KO001306
  • MoNA: KO001307
  • MoNA: KO001308
  • MoNA: KO001309
  • MoNA: MoNA034696
  • MoNA: MoNA034697
  • MoNA: MoNA034698
  • MoNA: MoNA035303
  • MoNA: MoNA035305
  • MoNA: MoNA035307
  • MoNA: MoNA037354
  • MoNA: MoNA038109
  • MoNA: MoNA038268
  • MoNA: MoNA_0008934
  • MoNA: MoNA_0009345
  • MoNA: MoNA_0009346
  • MoNA: MoNA_0009347
  • MoNA: MoNA_0009348
  • MoNA: PR010055
  • MoNA: PS026301
  • MoNA: PS026307
  • Metlin: METLIN_45931
  • Coconut NaturalProduct: CNP0152510.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00214 1.1.1.38 (S)-malate:NAD+ oxidoreductase (decarboxylating)
KEGG:R00216 1.1.1.40 (S)-malate:NADP+ oxidoreductase(oxaloacetate-decarboxylating)
KEGG:R00342 1.1.1.37 (S)-malate:NAD+ oxidoreductase
KEGG:R00343 1.1.1.82 (S)-malate:NADP+ oxidoreductase
KEGG:R00360 1.1.5.4 (S)-malate:oxygen oxidoreductase
KEGG:R00361 1.1.5.4 (S)-malate:quinone oxidoreductase
KEGG:R00406 2.8.3.22 succinyl-CoA:(S)-malate CoA-transferase
KEGG:R00472 2.3.3.9 acetyl-CoA:glyoxylate C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming);
KEGG:R01082 4.2.1.2 (S)-malate hydro-lyase (fumarate-forming)
KEGG:R01256 6.2.1.9 (S)-malate:CoA ligase (ADP-forming)
KEGG:R01257 1.1.5.4 (S)-malate:FAD oxidoreductase
KEGG:R01447 1.1.99.7 (S)-lactate:oxaloacetate oxidoreductase
KEGG:R03323 2.3.1.92 1-O-sinapoyl-beta-D-glucose:(S)-malate O-sinapoyltransferase
KEGG:R10612 3.1.2.30 (S)-malyl-CoA hydrolase
KEGG:R11074 4.1.1.101 (S)-malate carboxy-lyase
BioCyc:FUMHYDR-RXN 4.2.1.2 MAL<=>FUM + WATER
BioCyc:MALATE-DEHYDROGENASE-NADP+-RXN 1.1.1.82 MAL + NADP<=>PROTON + NADPH + OXALACETIC_ACID
BioCyc:1.1.1.39-RXN 1.1.1.38 MAL + NAD --> PYRUVATE + CARBON-DIOXIDE + NADH
BioCyc:MALATE-DEH-RXN 1.1.1.37 MAL + NAD<=>OXALACETIC_ACID + NADH + PROTON
BioCyc:MALIC-NADP-RXN 1.1.1.40 MAL + NADP --> PYRUVATE + CARBON-DIOXIDE + NADPH
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Organism Source

Taxonomy Source

  1. Aconitum seravschanicum [ncbi taxid: 246713]
  2. Aconitum tasiromontanum [ncbi taxid: ]
  3. Adansonia grandidieri [ncbi taxid: 69111]
  4. Aloe africana [ncbi taxid: 1080010]
  5. Aloe ferox [ncbi taxid: 117798]
  6. Aloe spicata [ncbi taxid: 992642]
  7. Aloe vera [ncbi taxid: 34199]
  8. Alstonia muelleriana [ncbi taxid: 1382056]
  9. Angelica acutiloba [ncbi taxid: 55605]
  10. Angelica gigas [ncbi taxid: 85712]
  11. Angelica sinensis [ncbi taxid: 165353]
  12. Aphyllocladus denticulatus [ncbi taxid: 2782251]
  13. Arabidopsis thaliana [ncbi taxid: 3702]
  14. Artemisia cina [ncbi taxid: 1473222]
  15. Aster sedifolius [ncbi taxid: ]
  16. Bassia muricata [ncbi taxid: 267505]
  17. Bupleurum chinense [ncbi taxid: 52451]
  18. Bupleurum falcatum [ncbi taxid: 46367]
  19. Bupleurum scorzonerifolium [ncbi taxid: 48105]
  20. Capsicum annuum [ncbi taxid: 4072]
  21. Caulocystis cephalornithos [ncbi taxid: 97150]
  22. Chelidonium majus [ncbi taxid: 71251]
  23. Cichorium glandulosum [ncbi taxid: 1405821]
  24. Cichorium intybus [ncbi taxid: 13427]
  25. Coreopsis nodosa [ncbi taxid: ]
  26. Cornus officinalis [ncbi taxid: 16906]
  27. Cytophaga hutchinsoni [ncbi taxid: ]
  28. Dacrydium cupressinum [ncbi taxid: 56890]
  29. Dendriopoterium menendezii [ncbi taxid: 137441]
  30. Dictyopteris australis [ncbi taxid: 531971]
  31. Dodonaea viscosa [ncbi taxid: 151065]
  32. Dysoxylum cumingianum [ncbi taxid: ]
  33. Enceliopsis argophylla [ncbi taxid: 191186]
  34. Epichloe festucae var. lolii [ncbi taxid: 73839]
  35. Eria mollis [ncbi taxid: ]
  36. Eriocheir sinensis [ncbi taxid: 95602]
  37. Escherichia coli [ncbi taxid: 562]
  38. Escherichia coli TS-1 [BSglnA] [ncbi taxid: ]
  39. Flacourtia jangomas [ncbi taxid: 112819]
  40. FOOD SAKE [ncbi taxid: ]
  41. Gadus morhua callarias [ncbi taxid: 8053]
  42. Glycine tomentella [ncbi taxid: 44015]
  43. Haematococcus lacustris [ncbi taxid: 44745]
  44. Hippophae rhamnoides [ncbi taxid: 193516]
  45. Homalomena occulta [ncbi taxid: 714477]
  46. Homo sapiens [ncbi taxid: 9606]
  47. Hypoxylon rubiginosum [ncbi taxid: 110542]
  48. Isaria fumosorosea [ncbi taxid: ]
  49. Isatis tinctoria [ncbi taxid: 161756]
  50. Justicia secunda [ncbi taxid: ]
  51. Kalanchoe daigremontiana [ncbi taxid: 23013]
  52. Lavandula vera [ncbi taxid: ]
  53. Melia azedarach [ncbi taxid: 155640]
  54. Melia azedarach var. toosendan [ncbi taxid: 71608]
  55. Miliusa velutina [ncbi taxid: 235758]
  56. Neobalanocarpus heimii [ncbi taxid: ]
  57. Nicotiana undulata [ncbi taxid: 118713]
  58. Onobrychis arenaria [ncbi taxid: 83864]
  59. Opunitia dillenii HAW. [ncbi taxid: ]
  60. Paeonia suffruticosa [ncbi taxid: 45171]
  61. Panax schinseng [ncbi taxid: ]
  62. Parthenium fruticosum [ncbi taxid: ]
  63. Passiflora incarnata [ncbi taxid: 159425]
  64. Penicillium spinulosum [ncbi taxid: 63822]
  65. Persicaria tinctoria [ncbi taxid: 96455]
  66. Phyllanthus emblica [ncbi taxid: ]
  67. Physalis alkekengi [ncbi taxid: ]
  68. Podocarpus spicata [ncbi taxid: ]
  69. Polygonum cuspidatum [ncbi taxid: 83819]
  70. Prunus mume [ncbi taxid: 102107]
  71. Psychotria stachyoides [ncbi taxid: 1277330]
  72. Pterocladiella tenuis [ncbi taxid: 947988]
  73. Punica granatum [ncbi taxid: 22663]
  74. Rattus rattus [ncbi taxid: 10117]
  75. Rehmannia glutinosa [ncbi taxid: 99300]
  76. Rheum hybrid [ncbi taxid: ]
  77. Rivularia firma [ncbi taxid: ]
  78. Rubia akane [ncbi taxid: ]
  79. Saccharomyces cerevisiae [ncbi taxid: 4932]
  80. Saccharomyces pastori [ncbi taxid: ]
  81. Schisandra chinensis [ncbi taxid: 50507]
  82. Schisandra sphenanthera [ncbi taxid: 13674]
  83. Senecio paludaffinis [ncbi taxid: 1892289]
  84. Senecio subdentatus [ncbi taxid: 2764669]
  85. Skimmia laureola [ncbi taxid: 354518]
  86. Sphaerella laricina [ncbi taxid: ]
  87. Streptomyces flocculus [ncbi taxid: ]
  88. Tachigalia paniculata [ncbi taxid: ]
  89. Taraxacum borealisinense [ncbi taxid: ]
  90. Taraxacum coreanum [ncbi taxid: 1041103]
  91. Taraxacum mongolicum [ncbi taxid: 90037]
  92. Taraxacum officinale [ncbi taxid: 50225]
  93. Taraxacum platycarpum [ncbi taxid: 170727]
  94. Teucrium yemense [ncbi taxid: ]
  95. Trigonella grandiflora [ncbi taxid: 1210110]
  96. Tripolium pannonicum [ncbi taxid: 74787]
  97. Tussilago farfara [ncbi taxid: 118778]
  98. Uvaria calamistrata [ncbi taxid: 672966]
  99. Ziziphus jujuba [ncbi taxid: 326968]

Pathway Synthetic

pathway id name
BioCyc:CALBI_PWY3B3-100 TCA cycle, aerobic respiration
BioCyc:CALBI_GLUCONEO-PWY gluconeogenesis
BioCyc:CALBI_MALATE-ASPARTATE-SHUTTLE-PWY aspartate degradation
BioCyc:CALBI_GLYOXYLATE-BYPASS glyoxylate cycle
WikiPathways:WP3583 Central carbon metabolism
PathBank:SMP0000802 TCA Cycle
PathBank:SMP0000808 Inner Membrane Transport
PathBank:SMP0000839 Gluconeogenesis from L-Malic Acid
PathBank:SMP0000847 Glycolate and Glyoxylate Degradation
PathBank:SMP0000983 Secondary Metabolites: Glyoxylate Cycle
PathBank:SMP0001018 TCA cycle (ubiquinol-2)
PathBank:SMP0001019 TCA cycle (ubiquinol-3)
PathBank:SMP0001020 TCA cycle (ubiquinol-4)
PathBank:SMP0001021 TCA cycle (ubiquinol-5)
PathBank:SMP0001022 TCA cycle (ubiquinol-6)
PathBank:SMP0001023 TCA cycle (ubiquinol-7)
PathBank:SMP0001024 TCA cycle (ubiquinol-8)
PathBank:SMP0001025 TCA cycle (ubiquinol-9)
PathBank:SMP0001026 TCA cycle (ubiquinol-10)
PathBank:SMP0002035 Glycolate and Glyoxylate Degradation II
View All Pathways