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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

2012-09-11 17:36:36 UTC

Update Date

2023-02-21 17:19:36 UTC

HMDB ID

HMDB0030406

Secondary Accession Numbers

HMDB30406

Metabolite Identification

Common Name

Homomethionine

Description

Homomethionine (CAS: 6094-76-4) 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). Homomethionine is possibly neutral. Homomethionine has been detected, but not quantified in, several different foods, such as lima beans, red huckleberries, catjang pea, Chinese chestnuts, and pepper (C. annuum). This could make homomethionine a potential biomarker for the consumption of these foods. Homomethionine is found in brassicas and is isolated from cabbage and horseradish.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-5-(methylsulfanyl)pentanoic acid	HMDB
5-(Methylsulfanyl)-L-norvaline	HMDB
5-(Methylthio)-L-norvaline	HMDB
5-(Methylthio)norvaline	HMDB
L-2-Amino-5-(methylthio)pentanoic acid	HMDB
L-Homomethionine	HMDB
Homomethionine	HMDB

Chemical Formula

C₆H₁₃NO₂S

Average Molecular Weight

163.24

Monoisotopic Molecular Weight

163.066699837

IUPAC Name

(2S)-2-amino-5-(methylsulfanyl)pentanoic acid

Traditional Name

L-homomethionine

CAS Registry Number

25148-30-5

SMILES

CSCCC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C6H13NO2S/c1-10-4-2-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1

InChI Key

SFSJZXMDTNDWIX-YFKPBYRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
Carbonyl group
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

homomethionine (CHEBI:50708 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	247 - 248 °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	14.4 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.7	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.23 m³·mol⁻¹	ChemAxon
Polarizability	17.54 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
DeepCCS	[M+H]+	132.359	30932474
DeepCCS	[M-H]-	128.966	30932474
DeepCCS	[M-2H]-	165.915	30932474
DeepCCS	[M+Na]+	141.064	30932474
AllCCS	[M+H]+	136.8	32859911
AllCCS	[M+H-H2O]+	133.0	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	143.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Homomethionine	CSCCC[C@H](N)C(O)=O	2473.0	Standard polar	33892256
Homomethionine	CSCCC[C@H](N)C(O)=O	1409.3	Standard non polar	33892256
Homomethionine	CSCCC[C@H](N)C(O)=O	1651.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Homomethionine,1TMS,isomer #1	CSCCC[C@H](N)C(=O)O[Si](C)(C)C	1484.2	Semi standard non polar	33892256
Homomethionine,1TMS,isomer #2	CSCCC[C@H](N[Si](C)(C)C)C(=O)O	1585.6	Semi standard non polar	33892256
Homomethionine,2TMS,isomer #1	CSCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1603.5	Semi standard non polar	33892256
Homomethionine,2TMS,isomer #1	CSCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1644.3	Standard non polar	33892256
Homomethionine,2TMS,isomer #2	CSCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1738.0	Semi standard non polar	33892256
Homomethionine,2TMS,isomer #2	CSCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1686.3	Standard non polar	33892256
Homomethionine,3TMS,isomer #1	CSCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1769.0	Semi standard non polar	33892256
Homomethionine,3TMS,isomer #1	CSCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1765.0	Standard non polar	33892256
Homomethionine,1TBDMS,isomer #1	CSCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1719.0	Semi standard non polar	33892256
Homomethionine,1TBDMS,isomer #2	CSCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1822.0	Semi standard non polar	33892256
Homomethionine,2TBDMS,isomer #1	CSCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2060.3	Semi standard non polar	33892256
Homomethionine,2TBDMS,isomer #1	CSCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2077.9	Standard non polar	33892256
Homomethionine,2TBDMS,isomer #2	CSCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2169.4	Semi standard non polar	33892256
Homomethionine,2TBDMS,isomer #2	CSCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2110.7	Standard non polar	33892256
Homomethionine,3TBDMS,isomer #1	CSCCC[C@@H](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	2447.0	Semi standard non polar	33892256
Homomethionine,3TBDMS,isomer #1	CSCCC[C@@H](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	2378.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Homomethionine 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 - Homomethionine 10V, Negative-QTOF	splash10-03di-2900000000-b27994d9bdf27c106754	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homomethionine 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homomethionine 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homomethionine 10V, Positive-QTOF	splash10-00xr-8900000000-f41144967a7cb9bcb59e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homomethionine 20V, Positive-QTOF	splash10-00di-9000000000-e1ed5ff83f70294a0af9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homomethionine 40V, Positive-QTOF	splash10-074i-9000000000-e59bf9ce1052495819b4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

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

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10329619

PDB ID

Not Available

ChEBI ID

50708

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 Homomethionine (HMDB0030406)

MOL for HMDB0030406 (Homomethionine)

3D MOL for HMDB0030406 (Homomethionine)

3D SDF for HMDB0030406 (Homomethionine)

3D-SDF for HMDB0030406 (Homomethionine)

PDB for HMDB0030406 (Homomethionine)

3D PDB for HMDB0030406 (Homomethionine)

SMILES for HMDB0030406 (Homomethionine)

INCHI for HMDB0030406 (Homomethionine)

Structure for HMDB0030406 (Homomethionine)

3D Structure for HMDB0030406 (Homomethionine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra