MiMeDB: Showing metabocard for diethyl tartrate (MMDBc0033444)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:48:52 UTC

Update Date

2024-04-30 20:09:27 UTC

Metabolite ID

MMDBc0033444

Metabolite Identification

Common Name

diethyl tartrate

Description

Diethyl tartrate is found in alcoholic beverages. Diethyl tartrate is a flavouring ingredient. Diethyl tartrate is present in sherry, white wine and red wine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900092D          

 14 13  0  0  0  0            999 V2000
    1.8711   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8724   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033444

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3

> <INCHI_KEY>
YSAVZVORKRDODB-UHFFFAOYSA-N

> <FORMULA>
C8H14O6

> <MOLECULAR_WEIGHT>
206.1932

> <EXACT_MASS>
206.07903818

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.82590493124443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-diethyl 2,3-dihydroxybutanedioate

> <ALOGPS_LOGP>
-0.57

> <JCHEM_LOGP>
-0.8233958673333333

> <ALOGPS_LOGS>
-0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.61208687388243

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.187076252689968

> <JCHEM_PKA_STRONGEST_BASIC>
-4.334902326969982

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
45.2488

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl tartrate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.493  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.496  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.826  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.162  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.827  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.161  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.495  -2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.827  -4.207   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      10.161  -0.357   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.494  -0.357   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.828  -1.897   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   13                                                       
CONECT    4    2   14                                                       
CONECT    5    6    7    9                                                  
CONECT    6    5    8   10                                                  
CONECT    7    5   11   13                                                  
CONECT    8    6   12   14                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    3    7                                                       
CONECT   14    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0033584
HETATM    1  C1  UNL     1       4.289   0.628  -0.163  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.787  -0.202  -1.318  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.377  -0.287  -1.263  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.738  -0.846  -0.166  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.482  -1.266   0.763  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.256  -0.942  -0.097  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.268  -0.398  -1.264  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.223  -0.189   1.131  1.00  0.00           C  
HETATM    9  O4  UNL     1       0.299  -0.731   2.300  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.685  -0.175   1.238  1.00  0.00           C  
HETATM   11  O5  UNL     1      -2.268  -0.608   2.266  1.00  0.00           O  
HETATM   12  O6  UNL     1      -2.527   0.307   0.234  1.00  0.00           O  
HETATM   13  C7  UNL     1      -3.941   0.310   0.362  1.00  0.00           C  
HETATM   14  C8  UNL     1      -4.474   0.909  -0.934  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.116   0.068   0.337  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.659   1.601  -0.549  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.468   0.846   0.567  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.033   0.302  -2.282  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.248  -1.233  -1.291  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.102  -1.989  -0.043  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.405  -0.373  -2.004  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.217   0.839   1.043  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.376  -0.084   3.033  1.00  0.00           H  
HETATM   24  H10 UNL     1      -4.286   0.989   1.173  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.355  -0.694   0.557  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.913   1.875  -1.069  1.00  0.00           H  
HETATM   27  H13 UNL     1      -5.550   1.100  -0.904  1.00  0.00           H  
HETATM   28  H14 UNL     1      -4.158   0.243  -1.766  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8   20
CONECT    7   21
CONECT    8    9   10   22
CONECT    9   23
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   24   25
CONECT   14   26   27   28
END

Synonyms

Value	Source
Diethyl tartric acid	Generator
Diethyl tartrate, (S-(r,r))-isomer	MeSH
Tartaric acid diethyl ester	MeSH
(+)-Diethyl L-tartrate	HMDB
(+)-Diethyl-L-tartrate	HMDB
(+)-Tartaric acid diethyl ester	HMDB
(-)-Diethyl-D-tartrate	HMDB
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, diethyl ester	HMDB
Butanedioic acid, 2,3-dihydroxy- (R-(r,r)), diethyl ester	HMDB
Butanedioic acid, 2,3-dihydroxy-, diethyl ester	HMDB
Diethyl (+)-tartrate	HMDB
Diethyl (2R,3R)-(+)-tartrate	HMDB
Diethyl (2R,3R)-tartrate	HMDB
Diethyl (R,R)(+)tartrate	HMDB
Diethyl 1,2-dihydroxy-1, 2-ethanedicarboxylate	HMDB
Diethyl 1,2-dihydroxy-1,2-ethanedicarboxylate	HMDB
Diethyl 2,3-dihydroxybutanedioate	HMDB
Diethyl 2,3-dihydroxysuccinate	HMDB
Diethyl ester(R,R)-tartaric acid	HMDB
Diethyl L-tartrate	HMDB
Diethyl tartarate	HMDB
Diethyl tartratene	HMDB
Diethyl-D-tartrate	HMDB
Ethyl (+)-tartrate	HMDB
Ethyl tartarate	HMDB
Ethyl tartrate	HMDB
FEMA 2378	HMDB
L-(+)-(Diethyl tartrate)	HMDB
L-(+)-Tartaric acid diethyl ester	HMDB
Racem-dimethoxysuccinic acid, dimethylester	HMDB
Racemic-dimethoxysuccinic acid, dimethyl ester	HMDB
Tartaric acid, diethyl ester	HMDB
Tartaric acid, diethyl ester (8ci)	HMDB
[-]-Tartaric acid diethyl ester	HMDB
1,4-Diethyl 2,3-dihydroxybutanedioic acid	Generator
Diethyl tartrate	MeSH

Molecular Formula

C₈H₁₄O₆

Average Mass

206.1932

Monoisotopic Mass

206.07903818

IUPAC Name

1,4-diethyl 2,3-dihydroxybutanedioate

Traditional Name

diethyl tartrate

CAS Registry Number

87-91-2

SMILES

CCOC(=O)C(O)C(O)C(=O)OCC

InChI Identifier

InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3

InChI Key

YSAVZVORKRDODB-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Monosaccharide
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Property	Value	Source
Water Solubility	150 g/L	ALOGPS
logP	-0.57	ALOGPS
logP	-0.82	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	11.19	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	45.25 m³·mol⁻¹	ChemAxon
Polarizability	19.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9800000000-c8afa7679c1da8f6dcf4	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-8091000000-3f2c3836910b38c720b3	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1980000000-44b3da6b525cf2b98079	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pba-8910000000-fb9f5f6ae1131bbc957d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9200000000-c7e8f2703213575e54a2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-5930000000-44a6e067f36cd3ecfab6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pba-9700000000-d7dccccaf18e1c2b0b1d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052b-9100000000-31a128b3a14622adebf2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0970000000-81c008c9c652deaca717	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-5900000000-2412716a9f69ba9ffece	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01vk-9100000000-9a0d3dd447b78f62159a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-5950000000-1a0c0d332cc4ca562f94	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fft-9500000000-cabce9ba65c18b6139ec	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-9000000000-d3a8b26bb1020e14a57a	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Sweat

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Sweat	Detected but not Quantified						Adult	Both	Normal	HMDB	26755145

External Links

HMDB ID

HMDB0033584

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011660

KNApSAcK ID

Not Available

Chemspider ID

13871489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethyl tartrate

METLIN ID

Not Available

PubChem Compound

62333

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Patel S, Shibamoto T: Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine. J Agric Food Chem. 2002 Sep 25;50(20):5649-53. doi: 10.1021/jf020337f. [PubMed:12236692 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for diethyl tartrate (MMDBc0033444)

MOL for #<Metabolite:0x00007f47044a3c18>

3D MOL for #<Metabolite:0x00007f47044a3c18>

3D SDF for #<Metabolite:0x00007f47044a3c18>

3D-SDF for #<Metabolite:0x00007f47044a3c18>

PDB for #<Metabolite:0x00007f47044a3c18>

3D PDB for #<Metabolite:0x00007f47044a3c18>

SMILES for #<Metabolite:0x00007f47044a3c18>

INCHI for #<Metabolite:0x00007f47044a3c18>

Structure for #<Metabolite:0x00007f47044a3c18>

3D Structure for #<Metabolite:0x00007f47044a3c18>