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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 20:08:54 UTC

Update Date

2021-09-26 22:48:54 UTC

HMDB ID

HMDB0242250

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Diacetyl-L-tartaric anhydride

Description

(+)-Diacetyl-L-tartaric anhydride, also known as DATAAN, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review a significant number of articles have been published on (+)-Diacetyl-L-tartaric anhydride. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+)-diacetyl-l-tartaric anhydride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+)-Diacetyl-L-tartaric anhydride is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652308282122182D          

 15 15  0  0  0  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614   -0.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242250

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1C(OC(C)=O)C(=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O7/c1-3(9)13-5-6(14-4(2)10)8(12)15-7(5)11/h5-6H,1-2H3

> <INCHI_KEY>
XAKITKDHDMPGPW-UHFFFAOYSA-N

> <FORMULA>
C8H8O7

> <MOLECULAR_WEIGHT>
216.145

> <EXACT_MASS>
216.027002598

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.150664289611704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(acetyloxy)-2,5-dioxooxolan-3-yl acetate

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.8123770576666667

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.779439880257069

> <JCHEM_PKA_STRONGEST_BASIC>
-6.647238986443337

> <JCHEM_POLAR_SURFACE_AREA>
95.97000000000003

> <JCHEM_REFRACTIVITY>
41.31100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(acetyloxy)-2,5-dioxooxolan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-AUG-21         0                                  
HETATM    1  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.915   0.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.379   1.096   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.595  -0.886   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
DATAAN	HMDB
O,O-Diacetyl tartaric acid anhydride	HMDB

Chemical Formula

C₈H₈O₇

Average Molecular Weight

216.145

Monoisotopic Molecular Weight

216.027002598

IUPAC Name

4-(acetyloxy)-2,5-dioxooxolan-3-yl acetate

Traditional Name

4-(acetyloxy)-2,5-dioxooxolan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(OC(C)=O)C(=O)OC1=O

InChI Identifier

InChI=1S/C8H8O7/c1-3(9)13-5-6(14-4(2)10)8(12)15-7(5)11/h5-6H,1-2H3

InChI Key

XAKITKDHDMPGPW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid anhydride
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.11	ALOGPS
logP	-0.81	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.31 m³·mol⁻¹	ChemAxon
Polarizability	18.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	136.663	30932474
DeepCCS	[M-H]-	133.483	30932474
DeepCCS	[M-2H]-	170.619	30932474
DeepCCS	[M+Na]+	146.158	30932474
AllCCS	[M+H]+	145.7	32859911
AllCCS	[M+H-H2O]+	141.9	32859911
AllCCS	[M+NH4]+	149.2	32859911
AllCCS	[M+Na]+	150.2	32859911
AllCCS	[M-H]-	142.5	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Diacetyl-L-tartaric anhydride	CC(=O)OC1C(OC(C)=O)C(=O)OC1=O	2655.0	Standard polar	33892256
(+)-Diacetyl-L-tartaric anhydride	CC(=O)OC1C(OC(C)=O)C(=O)OC1=O	1388.9	Standard non polar	33892256
(+)-Diacetyl-L-tartaric anhydride	CC(=O)OC1C(OC(C)=O)C(=O)OC1=O	1547.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Diacetyl-L-tartaric anhydride GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-fd120f2d166e0f6896b3	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Diacetyl-L-tartaric anhydride GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Diacetyl-L-tartaric anhydride 10V, Negative-QTOF	splash10-014i-0390000000-5fa7cf0a5ad74a9816c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Diacetyl-L-tartaric anhydride 20V, Negative-QTOF	splash10-0adj-9820000000-69ee46de20e71a391c9e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Diacetyl-L-tartaric anhydride 40V, Negative-QTOF	splash10-052f-9100000000-2f425e3a066d488705cd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Diacetyl-L-tartaric anhydride 10V, Positive-QTOF	splash10-014i-0690000000-ab4e69088090142d806e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Diacetyl-L-tartaric anhydride 20V, Positive-QTOF	splash10-066u-4900000000-23f9e076dc42442642c0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Diacetyl-L-tartaric anhydride 40V, Positive-QTOF	splash10-0006-9500000000-88d2d3d032a14a50fe85	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

86107

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95411

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (+)-Diacetyl-L-tartaric anhydride (HMDB0242250)

MOL for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

3D MOL for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

3D SDF for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

3D-SDF for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

PDB for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

3D PDB for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

SMILES for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

INCHI for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

Structure for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

3D Structure for HMDB0242250 ((+)-Diacetyl-L-tartaric anhydride)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra