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Showing NP-Card for Malic acid (NP0001271)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-12 20:26:05 UTC
NP-MRD IDNP0001271
Secondary Accession NumbersNone
Natural Product Identification
Common NameMalic acid
DescriptionMalic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionised form it is malate, an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001271 (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 NP0001271 (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 NP0001271 (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>
NP0001271

> <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 NP0001271 (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 NP0001271 (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 NP0001271 (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 NP0001271 (Malic acid)

O[C@@H](CC(O)=O)C(O)=O
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INCHI for NP0001271 (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 Number6915-15-7
SMILES
OC(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)
InChI KeyBJEPYKJPYRNKOW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-12View Spectrum
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
Not Available
Species
Species of Origin
Species NameSourceReference
Acorus calamusLOTUS Database
Actinidia polygamaLOTUS Database
African marigoldLOTUS Database
Agave americanaLOTUS Database
Allium cepaFooDB
Allium schoenoprasumFooDB
Aloe arborescensLOTUS Database
Aloe veraLOTUS Database
Ammodendron bifoliumLOTUS Database
Ananas comosusFooDB
Annona muricataFooDB
Annona squamosaFooDB
Apium graveolensFooDB
Arabidopsis thalianaKNApSAcK Database
Arbutus unedoLOTUS Database
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Beta vulgarisLOTUS Database
Betula pubescensLOTUS Database
Borago officinalisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Cacalia hastataLOTUS Database
Camellia sinensisLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Carica papaya L.FooDB
Catharanthus roseusLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Cichorium intybusFooDB
Citrus aurantiifoliaFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Cydonia oblongaFooDB
Daphnia magnaLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Eriobotrya japonicaFooDB
Eupatorium cannabinumLOTUS Database
Fagopyrum esculentumFooDB
Ficus caricaFooDB
Flacourtia inermisLOTUS Database
Foeniculum vulgareFooDB
Fumaria parvifloraLOTUS Database
Ginkgo bilobaFooDB
Glaucium flavumLOTUS Database
Glycine maxFooDB
Gossypium hirsutumLOTUS Database
Helianthus annuus L.FooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hypericum perforatumLOTUS Database
Ipomoea batatasLOTUS Database
Juglans regiaFooDB
Kalanchoe daigremontianaKNApSAcK Database
Lactuca sativaFooDB
Laetiporus sulphureusLOTUS Database
Ledebouria cooperiLOTUS Database
Lemna aequinoctialisLOTUS Database
Lepidium meyeniiLOTUS Database
Linum usitatissimumFooDB
Lotus corniculatusLOTUS Database
Lupinus albusFooDB
Lupinus luteusLOTUS Database
Malus pumilaFooDB
Mangifera indicaFooDB
Manihot esculentaLOTUS Database
Matricaria recutitaFooDB
Morus nigraLOTUS Database
Musa x paradisiacaFooDB
Mycoplasmopsis bovisLOTUS Database
Opuntia ficus-indicaLOTUS Database
Panax ginsengLOTUS Database
Paris fargesiiLOTUS Database
Passiflora edulisFooDB
Petroselinum crispumFooDB
Phyllostachys edulisLOTUS Database
Physalis philadelphica var. immaculataFooDB
Pimenta dioicaFooDB
Pisum sativumFooDB
Plantago majorLOTUS Database
Pleurotus ostreatusLOTUS Database
Populus balsamiferaLOTUS Database
Populus lasiocarpaLOTUS Database
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Prunus armeniacaFooDB
Prunus aviumLOTUS Database
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus mumeLOTUS Database
Punica granatumKNApSAcK Database
Pyrus communisFooDB
Rheum rhabarbarumFooDB
Rhodiola roseaLOTUS Database
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rosa spinosissimaLOTUS Database
Rubus idaeusFooDB
Saccharum officinarumLOTUS Database
Salmonella entericaLOTUS Database
Salvia officinalisFooDB
Sambucus ebulusLOTUS Database
Sambucus nigraFooDB
Scutellaria baicalensisLOTUS Database
Solanum lycopersicumLOTUS Database
Solanum lycopersicum var. lycopersicumFooDB
Solanum tuberosumFooDB
Spinacia oleraceaFooDB
Synechococcus elongatusLOTUS Database
Tamarindus indicaFooDB
Telekia speciosaLOTUS Database
Thymus transcaucasicusLOTUS Database
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Viburnum opulusLOTUS Database
Vicia fabaFooDB
Vitis vinifera L.FooDB
Zea mays L.FooDB
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 Point131 - 133 °CNot Available
Boiling Point332.00 to 334.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP-1.26Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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. Hem SL: Elimination of aluminum adjuvants. Vaccine. 2002 May 31;20 Suppl 3:S40-3. [PubMed:12184363 ]
  2. Spiteller M, Spiteller G: [Occurrence of alpha-alkyl-substituted malic acids, and beta-hydroxy-beta-alkyl-substituted dicarboxylic and tricarboxylic acid derivatives in normal urine (author's transl)]. J Chromatogr. 1979 Nov 11;164(3):319-29. [PubMed:544608 ]
  3. Anneroth G, Nordenram G, Bengtsson S: Effect of saliva stimulants (Hybrin and malic acid) on cervical root surfaces in vitro. Scand J Dent Res. 1980 Jun;88(3):214-8. [PubMed:6932087 ]
  4. Schumann C, Michlmayr H, Eder R, Del Hierro AM, Kulbe KD, Mathiesen G, Nguyen TH: Heterologous expression of Oenococcus oeni malolactic enzyme in Lactobacillus plantarum for improved malolactic fermentation. AMB Express. 2012 Mar 27;2(1):19. doi: 10.1186/2191-0855-2-19. [PubMed:22452826 ]
  5. Wang Z, Ye F, Feng Y, Xiao W, Song H, Zhao L, Lu R, Huang B, Liu Y, Wang W, Li Y, Ding Y, Zheng Y, Song X, Tan W, Wang Q: Discovery and Nanosized Preparations of (S,R)-Tylophorine Malate as Novel anti-SARS-CoV-2 Agents. ACS Med Chem Lett. 2021 Oct 24;12(11):1838-1844. doi: 10.1021/acsmedchemlett.1c00481. eCollection 2021 Nov 11. [PubMed:34745429 ]