Showing metabocard for Malic acid (MMDBc0000046)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:28:25 UTC
Update Date2024-04-30 19:30:55 UTC
Metabolite IDMMDBc0000046
Metabolite Identification
Common NameMalic acid
DescriptionMalic 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).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa4e000d110>

L-Malic acid.mol
  Mrv1652305271900182D          

  9  8  0  0  0  0            999 V2000
   -1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  2  9  1  6  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fa4e000d110>

HMDB0000156
     RDKit          3D
Malic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.7811   -0.0330    0.5208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507   -0.1542   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025   -1.2061   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409    0.8607    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.6144   -0.3021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5191    1.7081    0.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385   -0.5906    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3293   -0.5356    1.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8061   -1.8323    0.0254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2054   -1.4390   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770    0.8927    1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066    1.8398   -0.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    0.6280   -1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440    1.7204    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964   -2.4733   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  6
  6 14  1  0
  9 15  1  0
M  END
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3D SDF for #<Metabolite:0x00007fa4e000d110>

L-Malic acid.mol
  Mrv1652305271900182D          

  9  8  0  0  0  0            999 V2000
   -1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  2  9  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000046

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@@H](CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1

> <INCHI_KEY>
BJEPYKJPYRNKOW-REOHCLBHSA-N

> <FORMULA>
C4H6O5

> <MOLECULAR_WEIGHT>
134.0874

> <EXACT_MASS>
134.021523302

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.926274075509982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-hydroxybutanedioic acid

> <ALOGPS_LOGP>
-0.87

> <JCHEM_LOGP>
-1.1136414279999998

> <ALOGPS_LOGS>
0.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.127730317344291

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1983571934669475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.913035238851454

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
24.8752

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-malic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fa4e000d110>

HMDB0000156
     RDKit          3D
Malic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.7811   -0.0330    0.5208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507   -0.1542   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025   -1.2061   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409    0.8607    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.6144   -0.3021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5191    1.7081    0.1266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385   -0.5906    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3293   -0.5356    1.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8061   -1.8323    0.0254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2054   -1.4390   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770    0.8927    1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066    1.8398   -0.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    0.6280   -1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440    1.7204    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964   -2.4733   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  6
  6 14  1  0
  9 15  1  0
M  END
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PDB for #<Metabolite:0x00007fa4e000d110>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: L-Malic acid.mol                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.001   1.925   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -3.334  -0.385   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.001  -1.925   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.334   0.385   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.667  -1.925   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    7    8                                                  
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    2                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007fa4e000d110>

COMPND    HMDB0000156
HETATM    1  O1  UNL     1       2.781  -0.033   0.521  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.651  -0.154  -0.046  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.502  -1.206  -0.904  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.641   0.861   0.292  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.714   0.614  -0.302  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.519   1.708   0.127  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.339  -0.591   0.300  1.00  0.00           C  
HETATM    8  O4  UNL     1      -2.329  -0.536   1.049  1.00  0.00           O  
HETATM    9  O5  UNL     1      -0.806  -1.832   0.025  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.205  -1.439  -1.586  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.577   0.893   1.415  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.007   1.840  -0.092  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.717   0.628  -1.390  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.544   1.720   1.113  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.396  -2.473  -0.521  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5   11   12
CONECT    5    6    7   13
CONECT    6   14
CONECT    7    8    8    9
CONECT    9   15
END
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SMILES for #<Metabolite:0x00007fa4e000d110>

O[C@@H](CC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fa4e000d110>

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
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Synonyms
ValueSource
(-)-L-Malic acidChEBI
(S)-(-)-Hydroxysuccinic acidChEBI
L-2-Hydroxybutanedioic acidChEBI
L-Apple acidChEBI
MalateChEBI
Malic acidChEBI
S-2-Hydroxybutanedioic acidChEBI
L-MalateKegg
(-)-L-MalateGenerator
(S)-(-)-HydroxysuccinateGenerator
L-2-HydroxybutanedioateGenerator
S-2-HydroxybutanedioateGenerator
(-)-(S)-MalateHMDB
(-)-(S)-Malic acidHMDB
(-)-HydroxysuccinateHMDB
(-)-Hydroxysuccinic acidHMDB
(-)-Malic acidHMDB
(2S)-2-HydroxybutanedioateHMDB
(2S)-2-Hydroxybutanedioic acidHMDB
(S)-Hydroxy-butanedioateHMDB
(S)-Hydroxy-butanedioic acidHMDB
(S)-HydroxybutanedioateHMDB
(S)-Hydroxybutanedioic acidHMDB
(S)-Malic acidHMDB
Apple acidHMDB
L-(-)-Malic acidHMDB
L-HydroxybutanedioateHMDB
L-Hydroxybutanedioic acidHMDB
L-HydroxysuccinateHMDB
L-Hydroxysuccinic acidHMDB
S-(-)-MalateHMDB
S-(-)-Malic acidHMDB
(S)-MalateHMDB
L-Malic acidChEBI
(2S)-2-Hydroxysuccinic acidHMDB
(2S)-Malic acidHMDB
(S)-2-Hydroxysuccinic acidHMDB
2-Hydroxybutanedioic acidHMDB
2-Hydroxyethane-1,2-dicarboxylic acidHMDB
2-Hydroxysuccinic acidHMDB
Deoxytetraric acidHMDB
Hydroxybutanedioic acidHMDB
Hydroxysuccinic acidHMDB
Monohydroxybutanedioic acidHMDB
alpha-Hydroxysuccinic acidHMDB
α-Hydroxysuccinic acidHMDB
Molecular FormulaC4H6O5
Average Mass134.0874
Monoisotopic Mass134.021523302
IUPAC Name(2S)-2-hydroxybutanedioic acid
Traditional Name(-)-malic acid
CAS Registry Number97-67-6
SMILES
O[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI KeyBJEPYKJPYRNKOW-REOHCLBHSA-N