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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:59 UTC

Update Date

2023-02-21 17:21:13 UTC

HMDB ID

HMDB0031712

Secondary Accession Numbers

HMDB31712

Metabolite Identification

Common Name

(±)-Glycerol 1,2-diacetate

Description

(±)-Glycerol 1,2-diacetate belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Based on a literature review a small amount of articles have been published on (±)-Glycerol 1,2-diacetate.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7    8                                                       
CONECT    4    7   11                                                       
CONECT    5    1    9   11                                                  
CONECT    6    2   10   12                                                  
CONECT    7    3    4   12                                                  
CONECT    8    3                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    4    5                                                       
CONECT   12    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(±)-glycerol 1,2-diacetic acid	Generator
1,2,3-Propanetriol, 1,2-diacetate	HMDB
1,2-Diacetin	HMDB
1,2-Diacetylglycerol	HMDB
1,2-Diacylglycerol	HMDB
Glycerol 1,2-diacetate	HMDB

Chemical Formula

C₇H₁₂O₅

Average Molecular Weight

176.1672

Monoisotopic Molecular Weight

176.068473494

IUPAC Name

1-(acetyloxy)-3-hydroxypropan-2-yl acetate

Traditional Name

1,2,3-propanetriol, diacetate

CAS Registry Number

101364-64-1

SMILES

CC(=O)OCC(CO)OC(C)=O

InChI Identifier

InChI=1S/C7H12O5/c1-5(9)11-4-7(3-8)12-6(2)10/h7-8H,3-4H2,1-2H3

InChI Key

UXDDRFCJKNROTO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1,2-diacylglycerols

Alternative Parents

Substituents

1,2-acyl-sn-glycerol
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0031712)

Non-genetic or non-specified gene disorder

Lipotoxicity (HMDB: HMDB0031712)

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031712)

Source

Endogenous

Endogenous (HMDB: HMDB0031712)

Animal

Animal (HMDB: HMDB0031712)

Exogenous

Food

Food (HMDB: HMDB0031712)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031712)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031712)

Biochemical process

Lipid transport (HMDB: HMDB0031712)

Role

Biological role

Proinflammatory agent (HMDB: HMDB0031712)

Industrial application

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0031712)

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
Water Solubility	89.1 g/L	ALOGPS
logP	-0.3	ALOGPS
logP	-0.96	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	38.82 m³·mol⁻¹	ChemAxon
Polarizability	16.82 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.118	31661259
DarkChem	[M-H]-	134.351	31661259
DeepCCS	[M+H]+	142.427	30932474
DeepCCS	[M-H]-	139.181	30932474
DeepCCS	[M-2H]-	175.998	30932474
DeepCCS	[M+Na]+	151.438	30932474
AllCCS	[M+H]+	140.3	32859911
AllCCS	[M+H-H2O]+	136.6	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	144.8	32859911
AllCCS	[M-H]-	136.9	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Glycerol 1,2-diacetate	CC(=O)OCC(CO)OC(C)=O	2338.7	Standard polar	33892256
(??)-Glycerol 1,2-diacetate	CC(=O)OCC(CO)OC(C)=O	1179.8	Standard non polar	33892256
(??)-Glycerol 1,2-diacetate	CC(=O)OCC(CO)OC(C)=O	1284.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-Glycerol 1,2-diacetate,1TMS,isomer #1	CC(=O)OCC(CO[Si](C)(C)C)OC(C)=O	1301.3	Semi standard non polar	33892256
(??)-Glycerol 1,2-diacetate,1TBDMS,isomer #1	CC(=O)OCC(CO[Si](C)(C)C(C)(C)C)OC(C)=O	1524.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (±)-Glycerol 1,2-diacetate EI-B (Non-derivatized)	splash10-0udi-4900000000-5f2019ffbc66382d4dc1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (±)-Glycerol 1,2-diacetate EI-B (Non-derivatized)	splash10-0udi-4900000000-5f2019ffbc66382d4dc1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Glycerol 1,2-diacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9600000000-1bd2ae506f8a53bb6a4b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Glycerol 1,2-diacetate GC-MS (1 TMS) - 70eV, Positive	splash10-0fkl-9610000000-1997db11ebc7bfb7cc86	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Glycerol 1,2-diacetate 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 - (±)-Glycerol 1,2-diacetate 10V, Positive-QTOF	splash10-0006-0900000000-f49b1b877f24e1ecf2f6	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 20V, Positive-QTOF	splash10-066r-0900000000-993c787f868080495bb3	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 40V, Positive-QTOF	splash10-014l-0900000000-ddecc2c8a8b81e5505ac	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 10V, Positive-QTOF	splash10-0002-0900000000-3cb6d950c87a5cbc3681	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 20V, Positive-QTOF	splash10-0002-0900000000-3cb6d950c87a5cbc3681	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 40V, Positive-QTOF	splash10-000i-1900000000-8ce3fab009379469d5c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 10V, Positive-QTOF	splash10-0006-0900000000-03c7f592a76e4f66b0bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 20V, Positive-QTOF	splash10-066r-0900000000-c6633ca66af84c672fdb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 40V, Positive-QTOF	splash10-014l-0900000000-250522612223c4865819	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 10V, Negative-QTOF	splash10-0a4r-9000000000-fb5f70e4ee8f862e3d32	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 20V, Negative-QTOF	splash10-0a4l-9000000000-30c7f0c3c0f0990dd4a0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 40V, Negative-QTOF	splash10-0a4i-9000000000-fd69c25a70412d31a329	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 10V, Positive-QTOF	splash10-014j-7900000000-0894a70985717168c940	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 20V, Positive-QTOF	splash10-05oy-9100000000-b96b15440f3f70c9a518	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Glycerol 1,2-diacetate 40V, Positive-QTOF	splash10-0005-9000000000-bddd23894022358efb87	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Inositol phosphate metabolism	Not Available
Lamivudine Metabolism Pathway		Not Available

Normal Concentrations

Not Available

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

FDB008375

KNApSAcK ID

Not Available

Chemspider ID

59412

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66021

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (±)-Glycerol 1,2-diacetate (HMDB0031712)

MOL for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

3D MOL for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

3D SDF for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

3D-SDF for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

PDB for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

3D PDB for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

SMILES for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

INCHI for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

Structure for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

3D Structure for HMDB0031712 ((±)-Glycerol 1,2-diacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra