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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:30:20 UTC

Update Date

2023-02-21 17:18:46 UTC

HMDB ID

HMDB0029423

Secondary Accession Numbers

HMDB29423

Metabolite Identification

Common Name

Acetylhomoserine

Description

Acetylhomoserine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Acetylhomoserine exists in all eukaryotes, ranging from yeast to plants to humans. Acetylhomoserine is found, on average, in the highest concentration within common peas (Pisum sativum). Acetylhomoserine has also been detected, but not quantified in, milk (cow) and pulses. This could make acetylhomoserine a potential biomarker for the consumption of these foods. Acetylhomoserine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Acetylhomoserine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Acetoxy-2-aminobutanoic acid	HMDB
Homoserine acetate	HMDB
O-Acetyl-L-homoserine	HMDB
O-Acetylhomoserine	HMDB

Chemical Formula

C₆H₁₁NO₄

Average Molecular Weight

161.1558

Monoisotopic Molecular Weight

161.068807845

IUPAC Name

4-(acetyloxy)-2-aminobutanoic acid

Traditional Name

O-acetylhomoserine

CAS Registry Number

7540-67-2

SMILES

CC(=O)OCCC(N)C(O)=O

InChI Identifier

InChI=1S/C6H11NO4/c1-4(8)11-3-2-5(7)6(9)10/h5H,2-3,7H2,1H3,(H,9,10)

InChI Key

FCXZBWSIAGGPCB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Carboxylic acid ester
Amino acid
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetate ester (CHEBI:7671 )
non-proteinogenic alpha-amino acid (CHEBI:7671 )

Ontology

Physiological effect

Health effect

Attachment loss (FooDB: )
Periodontal Probing Depth (FooDB: )

Disposition

Biological location

Cellular substructure

Cytoplasm (FooDB: )
Extracellular (FooDB: )

Route of exposure

Enteral

Ingestion (FooDB: )

Source

Endogenous

Endogenous (FooDB: )

Plant

Fabaceae (FooDB: )

Exogenous

Food

Food (FooDB: )

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 °C	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	83.9 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.4	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Acidic)	2.02	ChemAxon
pKa (Strongest Basic)	9.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.62 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.06 m³·mol⁻¹	ChemAxon
Polarizability	15.54 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]+	135.934	31661259
DarkChem	[M-H]-	131.798	31661259
DeepCCS	[M+H]+	129.893	30932474
DeepCCS	[M-H]-	126.506	30932474
DeepCCS	[M-2H]-	163.43	30932474
DeepCCS	[M+Na]+	138.517	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.8	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.3	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	136.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetylhomoserine	CC(=O)OCCC(N)C(O)=O	2280.3	Standard polar	33892256
Acetylhomoserine	CC(=O)OCCC(N)C(O)=O	1273.9	Standard non polar	33892256
Acetylhomoserine	CC(=O)OCCC(N)C(O)=O	1607.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetylhomoserine,1TMS,isomer #1	CC(=O)OCCC(N)C(=O)O[Si](C)(C)C	1389.0	Semi standard non polar	33892256
Acetylhomoserine,1TMS,isomer #2	CC(=O)OCCC(N[Si](C)(C)C)C(=O)O	1489.9	Semi standard non polar	33892256
Acetylhomoserine,2TMS,isomer #1	CC(=O)OCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1509.6	Semi standard non polar	33892256
Acetylhomoserine,2TMS,isomer #1	CC(=O)OCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1535.7	Standard non polar	33892256
Acetylhomoserine,2TMS,isomer #2	CC(=O)OCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1700.2	Semi standard non polar	33892256
Acetylhomoserine,2TMS,isomer #2	CC(=O)OCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1610.3	Standard non polar	33892256
Acetylhomoserine,3TMS,isomer #1	CC(=O)OCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1741.4	Semi standard non polar	33892256
Acetylhomoserine,3TMS,isomer #1	CC(=O)OCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1645.3	Standard non polar	33892256
Acetylhomoserine,1TBDMS,isomer #1	CC(=O)OCCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1611.5	Semi standard non polar	33892256
Acetylhomoserine,1TBDMS,isomer #2	CC(=O)OCCC(N[Si](C)(C)C(C)(C)C)C(=O)O	1724.7	Semi standard non polar	33892256
Acetylhomoserine,2TBDMS,isomer #1	CC(=O)OCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1926.8	Semi standard non polar	33892256
Acetylhomoserine,2TBDMS,isomer #1	CC(=O)OCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1955.1	Standard non polar	33892256
Acetylhomoserine,2TBDMS,isomer #2	CC(=O)OCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2104.0	Semi standard non polar	33892256
Acetylhomoserine,2TBDMS,isomer #2	CC(=O)OCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2014.6	Standard non polar	33892256
Acetylhomoserine,3TBDMS,isomer #1	CC(=O)OCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2360.2	Semi standard non polar	33892256
Acetylhomoserine,3TBDMS,isomer #1	CC(=O)OCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2259.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-5d1c4502d7e1d94d2116	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9700000000-c7795d0413201e3d24c5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhomoserine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Acetylhomoserine 10V, Positive-QTOF	splash10-02t9-2900000000-ed6eb8917a78bbf88100	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 20V, Positive-QTOF	splash10-066r-9400000000-2d4b4fcb94787defa8f9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 40V, Positive-QTOF	splash10-0a4l-9000000000-52d7635274c83393203b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 10V, Negative-QTOF	splash10-03di-5900000000-627d1582fcc358f1c9ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 20V, Negative-QTOF	splash10-0a4i-9300000000-33fa740698e617abe91c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 40V, Negative-QTOF	splash10-0a4l-9000000000-f1ca7f1c659dcdc0fc69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 10V, Negative-QTOF	splash10-0a4i-9600000000-df7f85a9e63e548714b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 20V, Negative-QTOF	splash10-0a4i-9300000000-174e28ead7bdd58b982f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 40V, Negative-QTOF	splash10-0a4i-9000000000-9e2bab7e30574fd7ec65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 10V, Positive-QTOF	splash10-01bc-9800000000-91e09b71291eb6f7e066	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 20V, Positive-QTOF	splash10-0ab9-9200000000-76477e3d3ed37a7cc503	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhomoserine 40V, Positive-QTOF	splash10-0a4i-9000000000-c885f1b452d06f434c0d	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000523

KNApSAcK ID

Not Available

Chemspider ID

513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

528

PDB ID

Not Available

ChEBI ID

7671

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Acetylhomoserine (HMDB0029423)

MOL for HMDB0029423 (Acetylhomoserine)

3D MOL for HMDB0029423 (Acetylhomoserine)

3D SDF for HMDB0029423 (Acetylhomoserine)

3D-SDF for HMDB0029423 (Acetylhomoserine)

PDB for HMDB0029423 (Acetylhomoserine)

3D PDB for HMDB0029423 (Acetylhomoserine)

SMILES for HMDB0029423 (Acetylhomoserine)

INCHI for HMDB0029423 (Acetylhomoserine)

Structure for HMDB0029423 (Acetylhomoserine)

3D Structure for HMDB0029423 (Acetylhomoserine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra