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Showing NP-Card for diethyl malate (NP0283706)

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Record Information
Version2.0
Created at2022-09-09 11:04:27 UTC
Updated at2022-09-09 11:04:28 UTC
NP-MRD IDNP0283706
Secondary Accession NumbersNone
Natural Product Identification
Common Namediethyl malate
DescriptionDiethyl L-malate 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. Diethyl L-malate is an extremely weak basic (essentially neutral) compound (based on its pKa). diethyl malate is found in Diospyros maritima, Rosa laevigata and Vitis vinifera. A malate ester obtained by the formal condensation of the two carboxy groups of malic acid with two molecules of ethanol respectively.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0283706 (diethyl malate)


  Mrv0541 02241215492D          

 13 12  0  0  0  0            999 V2000
    1.0534    1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    0.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874   -0.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4953    0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745   -1.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3607   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    0.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -0.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536   -1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7890    0.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953   -0.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0283706 (diethyl malate)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.4715    0.8504    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0174   -0.1198    1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115   -0.0091    1.3406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383   -0.2792    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.6133   -0.8773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3643   -0.1599    0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960   -0.4933   -0.9568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1426    0.3851   -1.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.4313   -0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317    0.3358   -1.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -1.1817   -0.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319   -1.1178    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4624    0.2523    0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    1.6848    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5037    1.2403    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4923    0.3063   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2106   -1.1783    0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390    0.0288    2.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496    0.8905    0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039   -0.8819    1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951   -1.5034   -1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105    1.1323   -1.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -1.8028    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4319   -1.5069   -0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    0.5358    1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    0.1513    0.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2997    0.9960   -0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  6
  8 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0283706 (diethyl malate)


  Mrv0541 02241215492D          

 13 12  0  0  0  0            999 V2000
    1.0534    1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    0.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874   -0.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4953    0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745   -1.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3607   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    0.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -0.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536   -1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7890    0.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953   -0.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC(O)C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O5/c1-3-12-7(10)5-6(9)8(11)13-4-2/h6,9H,3-5H2,1-2H3

> <INCHI_KEY>
VKNUORWMCINMRB-UHFFFAOYSA-N

> <FORMULA>
C8H14O5

> <MOLECULAR_WEIGHT>
190.1938

> <EXACT_MASS>
190.084123558

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.75039341481834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-diethyl 2-hydroxybutanedioate

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
-0.10823740666666679

> <ALOGPS_LOGS>
-0.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.442701423671714

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9173623972859923

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
43.9106

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-diethyl 2-hydroxybutanedioate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0283706 (diethyl malate)

Download
PDB for NP0283706 (diethyl malate)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.966   1.960   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.990   0.418   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.336  -0.329   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.658   0.467   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.699  -1.914   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.673  -0.372   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.674   0.375   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.995  -0.421   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.967  -1.960   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.339   0.326   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.005  -0.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.658  -0.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.005   0.280   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3   11                                                       
CONECT    5    6                                                            
CONECT    6    2    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   12                                                       
CONECT   11    4                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0283706 (diethyl malate)
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SMILES for NP0283706 (diethyl malate)
CCOC(=O)CC(O)C(=O)OCC
Download
INCHI for NP0283706 (diethyl malate)
InChI=1S/C8H14O5/c1-3-12-7(10)5-6(9)8(11)13-4-2/h6,9H,3-5H2,1-2H3
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View in JSmol
Synonyms
ValueSource
Diethyl L-malic acidGenerator
Butanedioic acid, 2-hydroxy-, 1,4-diethyl esterHMDB
Butanedioic acid, hydroxy-, diethyl esterHMDB
Diethyl (1)-malateHMDB
Diethyl hydroxybutanedioateHMDB
Diethyl hydroxybutanoateHMDB
Diethyl malateHMDB
Ethyl DL-malateHMDB
Ethyl malateHMDB
Ethyl-DL-malateHMDB
Hydroxy-diethyl ester(.+/-.)-butanedioic acidHMDB
L-(-)-Malic acid diethyl esterHMDB
Malic acid, diethyl esterHMDB
Diethyl malate, (R)-isomerHMDB
Diethyl malate, (+-)-isomerHMDB
Diethyl malate, (S)-isomerHMDB
Diethyl malic acidGenerator
Diethyl D-malic acidGenerator
Chemical FormulaC8H14O5
Average Mass190.1938 Da
Monoisotopic Mass190.08412 Da
IUPAC Name1,4-diethyl 2-hydroxybutanedioate
Traditional Name1,4-diethyl 2-hydroxybutanedioate
CAS Registry NumberNot Available
SMILES
CCOC(=O)CC(O)C(=O)OCC
InChI Identifier
InChI=1S/C8H14O5/c1-3-12-7(10)5-6(9)8(11)13-4-2/h6,9H,3-5H2,1-2H3
InChI KeyVKNUORWMCINMRB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Diospyros maritimaLOTUS Database
Rosa laevigataLOTUS Database
Vitis viniferaLOTUS 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
  • Fatty acid ester
    • 

  • Beta-hydroxy acid
    • 

  • Fatty acyl
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.34ALOGPS
logP-0.11ChemAxon
logS-0.29ALOGPS
pKa (Strongest Acidic)12.44ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.91 m³·mol⁻¹ChemAxon
Polarizability18.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040220  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019933  
KNApSAcK IDNot Available
Chemspider ID22619  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24197  
PDB IDNot Available
ChEBI ID87368  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]