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Showing NP-Card for L-Malic acid (NP0001067)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:44 UTC
NP-MRD IDNP0001067
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Malic acid
DescriptionMalic acid 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 of 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.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001067 (L-Malic acid)

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
Download

3D MOL for NP0001067 (L-Malic acid)

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
Download

3D SDF for NP0001067 (L-Malic acid)

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>
NP0001067

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001067 (L-Malic acid)

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
Download

PDB for NP0001067 (L-Malic acid)

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 NP0001067 (L-Malic acid)

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 NP0001067 (L-Malic acid)

O[C@@H](CC(O)=O)C(O)=O
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INCHI for NP0001067 (L-Malic acid)

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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View in JSmol
Synonyms
ValueSource
(-)-L-Malic acidChEBI
(S)-(-)-Hydroxysuccinic acidChEBI
L-2-Hydroxybutanedioic acidChEBI
L-Apple acidChEBI
L-Malic acidChEBI
MalateChEBI
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
(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
Malic acidChEBI
Chemical FormulaC4H6O5
Average Mass134.0874 Da
Monoisotopic Mass134.02152 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-03View Spectrum
Species
Species of Origin
Species NameSourceReference
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Acorus calamusLOTUS Database
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloe arborescensLOTUS Database
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Angelica sinensisLOTUS Database
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arbutus unedoLOTUS Database
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Betula pubescensLOTUS Database
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cacalia hastataLOTUS Database
Cajanus cajanFooDB
Canarium ovatumFooDB
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Eleusine coracanaLOTUS Database
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flacourtia inermisLOTUS Database
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glaucium flavumLOTUS Database
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Kalanchoe daigremontianaKNApSAcK Database
Lablab purpureusFooDB
Lactuca sativaFooDB
Laetiporus sulphureusLOTUS Database
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium meyeniiLOTUS Database
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Opunitia dillenii HAW.-
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Opuntia strictaLOTUS Database
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Plantago majorLOTUS Database
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumKNApSAcK Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rehmannia glutinosaLOTUS Database
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Scutellaria baicalensisLOTUS Database
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Viburnum opulusLOTUS Database
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 °CNot Available
Boiling Point332.00 to 334.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.85 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.520 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility218 g/LALOGPS
logP-0.87ALOGPS
logP-1.1ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.88 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000156
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030170
KNApSAcK IDC00001192
Chemspider ID193317
KEGG Compound IDC00149
BioCyc IDMAL
BiGG ID34045
Wikipedia LinkMalic acid
METLIN IDNot Available
PubChem Compound222656
PDB IDNot Available
ChEBI ID30797
Good Scents IDrw1597161
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  3. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
  4. Fang TJ, Dalmasso JP: Antimicrobial activity of sulfur dioxide to certain lactic acid bacteria isolated from wines. Zhonghua Min Guo Wei Sheng Wu Ji Mian Yi Xue Za Zhi. 1993 Aug;26(3):116-31. [PubMed:7982367 ]
  5. Splittstoesser DF, McLellan MR, Churey JJ: Heat resistance of Escherichia coli O157:H7 in apple juice. J Food Prot. 1996 Mar;59(3):226-9. [PubMed:10463437 ]
  6. Denayrolles M, Aigle M, Lonvaud-Funel A: Cloning and sequence analysis of the gene encoding Lactococcus lactis malolactic enzyme: relationships with malic enzymes. FEMS Microbiol Lett. 1994 Feb 1;116(1):79-86. [PubMed:8132158 ]