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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:01:29 UTC

Update Date

2023-02-21 17:17:49 UTC

HMDB ID

HMDB0012485

Secondary Accession Numbers

HMDB12485

Metabolite Identification

Common Name

(R)-glycerol 1-acetate

Description

Glycerol acetate is the ester produced from the esterification of glycerol with acetic acid. Multiple products can be produced from this reaction; these include the monoacetylglycerols (MAG), diacetylglycerols (DAG), and triacetalglycerol (TAG) (also known as triacetin). (Wikipedia).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-Glycerol 1-acetic acid	Generator
1-Monoacetylglycerol	HMDB
Acetylglycerol	HMDB
alpha-Monoacetin	HMDB
Propanetriol 1-acetate	HMDB
(2S)-2,3-Dihydroxypropyl acetic acid	Generator

Chemical Formula

C₅H₁₀O₄

Average Molecular Weight

134.1305

Monoisotopic Molecular Weight

134.057908808

IUPAC Name

(2S)-2,3-dihydroxypropyl acetate

Traditional Name

(2S)-2,3-dihydroxypropyl acetate

CAS Registry Number

106-61-6

SMILES

CC(=O)OC[C@@H](O)CO

InChI Identifier

InChI=1S/C5H10O4/c1-4(7)9-3-5(8)2-6/h5-6,8H,2-3H2,1H3/t5-/m0/s1

InChI Key

KMZHZAAOEWVPSE-YFKPBYRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

1-monoacylglycerols

Alternative Parents

Substituents

1-acyl-sn-glycerol
Secondary alcohol
Carboxylic acid ester
1,2-diol
Monocarboxylic acid or derivatives
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

Not Available

Disposition

Biological location

Cellular substructure

Cell membrane (HMDB: HMDB0012485)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012485)

Source

Endogenous

Endogenous (HMDB: HMDB0012485)

Animal

Animal (HMDB: HMDB0012485)

Exogenous

Food

Food (HMDB: HMDB0012485)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012485)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012485)

Lipid metabolism pathway (HMDB: HMDB0012485)

Biochemical process

Lipid transport (HMDB: HMDB0012485)

Role

Biological role

Energy source (HMDB: HMDB0012485)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	769 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.4	ChemAxon
logS	0.76	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	29.67 m³·mol⁻¹	ChemAxon
Polarizability	13.11 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]+	129.172	31661259
DarkChem	[M-H]-	121.982	31661259
DeepCCS	[M+H]+	124.224	30932474
DeepCCS	[M-H]-	121.131	30932474
DeepCCS	[M-2H]-	157.938	30932474
DeepCCS	[M+Na]+	133.102	30932474
AllCCS	[M+H]+	131.8	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	135.6	32859911
AllCCS	[M+Na]+	136.6	32859911
AllCCS	[M-H]-	127.8	32859911
AllCCS	[M+Na-2H]-	130.6	32859911
AllCCS	[M+HCOO]-	133.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	1.83 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7101 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	132.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	867.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	333.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	57.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	57.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	266.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	262.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	367.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	630.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	71.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	933.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	614.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	265.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	308.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-glycerol 1-acetate	CC(=O)OC[C@@H](O)CO	2185.5	Standard polar	33892256
(R)-glycerol 1-acetate	CC(=O)OC[C@@H](O)CO	1133.4	Standard non polar	33892256
(R)-glycerol 1-acetate	CC(=O)OC[C@@H](O)CO	1172.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-glycerol 1-acetate,1TMS,isomer #1	CC(=O)OC[C@H](CO)O[Si](C)(C)C	1180.5	Semi standard non polar	33892256
(R)-glycerol 1-acetate,1TMS,isomer #2	CC(=O)OC[C@@H](O)CO[Si](C)(C)C	1188.9	Semi standard non polar	33892256
(R)-glycerol 1-acetate,2TMS,isomer #1	CC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	1294.0	Semi standard non polar	33892256
(R)-glycerol 1-acetate,1TBDMS,isomer #1	CC(=O)OC[C@H](CO)O[Si](C)(C)C(C)(C)C	1413.8	Semi standard non polar	33892256
(R)-glycerol 1-acetate,1TBDMS,isomer #2	CC(=O)OC[C@@H](O)CO[Si](C)(C)C(C)(C)C	1418.0	Semi standard non polar	33892256
(R)-glycerol 1-acetate,2TBDMS,isomer #1	CC(=O)OC[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1740.2	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 - (R)-glycerol 1-acetate GC-MS (2 TMS) - 70eV, Positive	splash10-0ukl-9450000000-c41193b4a5ab62f8301f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-glycerol 1-acetate 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 - (R)-glycerol 1-acetate 10V, Positive-QTOF	splash10-0udi-0900000000-eaa09ba6ebf588eb5b6b	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 20V, Positive-QTOF	splash10-0udi-0900000000-eaa09ba6ebf588eb5b6b	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 40V, Positive-QTOF	splash10-0yw6-6900000000-ed93f8f385433ec956b3	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 10V, Positive-QTOF	splash10-0006-0900000000-b4822a14e1112ad5a7d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 20V, Positive-QTOF	splash10-0006-0900000000-b4822a14e1112ad5a7d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 40V, Positive-QTOF	splash10-0005-9500000000-acfdf7effa393527a7cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 10V, Positive-QTOF	splash10-05oy-9100000000-3c65f9c4e0b5fa858427	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 20V, Positive-QTOF	splash10-052g-9000000000-dc65e0978436cb65ed7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 40V, Positive-QTOF	splash10-0006-9000000000-2b3ffdc8c96042be0bd1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 10V, Positive-QTOF	splash10-0udi-0900000000-e039e2676a44191e854c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 20V, Positive-QTOF	splash10-0udi-0900000000-e039e2676a44191e854c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 40V, Positive-QTOF	splash10-02to-8900000000-0548f7ddac7f200459a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 10V, Negative-QTOF	splash10-0a4i-9000000000-cd39551028ded46b72c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-7f533bb402f13c7f1351	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-glycerol 1-acetate 40V, Negative-QTOF	splash10-0a4i-9000000000-57efb85ba2c5a7c82d4c	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB029093

KNApSAcK ID

Not Available

Chemspider ID

5361868

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6993818

PDB ID

Not Available

ChEBI ID

173558

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1495631

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (R)-glycerol 1-acetate (HMDB0012485)

MOL for HMDB0012485 ((R)-glycerol 1-acetate)

3D MOL for HMDB0012485 ((R)-glycerol 1-acetate)

3D SDF for HMDB0012485 ((R)-glycerol 1-acetate)

3D-SDF for HMDB0012485 ((R)-glycerol 1-acetate)

PDB for HMDB0012485 ((R)-glycerol 1-acetate)

3D PDB for HMDB0012485 ((R)-glycerol 1-acetate)

SMILES for HMDB0012485 ((R)-glycerol 1-acetate)

INCHI for HMDB0012485 ((R)-glycerol 1-acetate)

Structure for HMDB0012485 ((R)-glycerol 1-acetate)

3D Structure for HMDB0012485 ((R)-glycerol 1-acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra