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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:06 UTC

HMDB ID

HMDB0000719

Secondary Accession Numbers

HMDB00719

Metabolite Identification

Common Name

L-Homoserine

Description

Homoserine is a more reactive variant of the amino acid serine. In this variant, the hydroxyl side chain contains an additional CH2 group which brings the hydroxyl group closer to its own carboxyl group, allowing it to chemically react to form a five-membered ring. This occurs at the point that amino acids normally join to their neighbours in a peptide bond. Homoserine is therefore unsuitable for forming proteins and has been eliminated from the repertoire of amino acids used by living things. Homoserine is the final product on the C-terminal end of the N-terminal fragment following a cyanogen bromide cleavage. (wikipedia). Homoserine is also a microbial metabolite.

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-4-hydroxybutanoic acid	ChEBI
2-Amino-4-hydroxybutanoic acid	ChEBI
2-Amino-4-hydroxybutyric acid	ChEBI
Homoserine	ChEBI
(2S)-2-Amino-4-hydroxybutanoate	Generator
2-Amino-4-hydroxybutanoate	Generator
2-Amino-4-hydroxybutyrate	Generator
(S)-2-Amino-4-hydroxy-butanoate	HMDB
(S)-2-Amino-4-hydroxy-butanoic acid	HMDB
(S)-2-Amino-4-hydroxybutanoate	HMDB
(S)-2-Amino-4-hydroxybutanoic acid	HMDB
(S)-Homoserine	HMDB
2-Amino-4-hydroxy-butyrate	HMDB
2-Amino-4-hydroxy-butyric acid	HMDB
2-Amino-4-hydroxy-L-butyrate	HMDB
2-Amino-4-hydroxy-L-butyric acid	HMDB
Homoserine L-isomer	HMDB
L Isomer OF homoserine	HMDB
L-Isomer OF homoserine	HMDB

Chemical Formula

C₄H₉NO₃

Average Molecular Weight

119.1192

Monoisotopic Molecular Weight

119.058243159

IUPAC Name

(2S)-2-amino-4-hydroxybutanoic acid

Traditional Name

L-homoserine

CAS Registry Number

672-15-1

SMILES

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

InChI Identifier

InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

InChI Key

UKAUYVFTDYCKQA-VKHMYHEASA-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
Short-chain hydroxy acid
Fatty acid
1,3-aminoalcohol
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

homoserine (CHEBI:15699 )
Other amino acids (C00263 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203 °C	Not Available
Boiling Point	368.72 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000 mg/mL	Not Available
LogP	-1.289 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	121.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002068
[M+H]+	Not Available	126.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002068

Predicted Molecular Properties

Property	Value	Source
Water Solubility	423 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.8	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	2.22	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.91 m³·mol⁻¹	ChemAxon
Polarizability	11.44 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]+	125.815	31661259
DarkChem	[M-H]-	120.208	31661259
AllCCS	[M+H]+	129.088	32859911
AllCCS	[M-H]-	122.166	32859911
DeepCCS	[M+H]+	122.108	30932474
DeepCCS	[M-H]-	118.788	30932474
DeepCCS	[M-2H]-	155.67	30932474
DeepCCS	[M+Na]+	130.729	30932474
AllCCS	[M+H]+	129.1	32859911
AllCCS	[M+H-H2O]+	124.9	32859911
AllCCS	[M+NH4]+	133.0	32859911
AllCCS	[M+Na]+	134.1	32859911
AllCCS	[M-H]-	122.2	32859911
AllCCS	[M+Na-2H]-	125.4	32859911
AllCCS	[M+HCOO]-	128.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Homoserine	N[C@@H](CCO)C(O)=O	2087.4	Standard polar	33892256
L-Homoserine	N[C@@H](CCO)C(O)=O	1176.9	Standard non polar	33892256
L-Homoserine	N[C@@H](CCO)C(O)=O	1527.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Homoserine,1TMS,isomer #1	C[Si](C)(C)OCC[C@H](N)C(=O)O	1313.9	Semi standard non polar	33892256
L-Homoserine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCO	1231.9	Semi standard non polar	33892256
L-Homoserine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCO)C(=O)O	1350.8	Semi standard non polar	33892256
L-Homoserine,2TMS,isomer #1	C[Si](C)(C)OCC[C@H](N)C(=O)O[Si](C)(C)C	1354.9	Semi standard non polar	33892256
L-Homoserine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCO[Si](C)(C)C)C(=O)O	1426.7	Semi standard non polar	33892256
L-Homoserine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCO)C(=O)O[Si](C)(C)C	1383.3	Semi standard non polar	33892256
L-Homoserine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCO)C(=O)O)[Si](C)(C)C	1527.7	Semi standard non polar	33892256
L-Homoserine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1471.3	Semi standard non polar	33892256
L-Homoserine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1519.5	Standard non polar	33892256
L-Homoserine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1571.5	Standard polar	33892256
L-Homoserine,3TMS,isomer #2	C[Si](C)(C)OCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1609.5	Semi standard non polar	33892256
L-Homoserine,3TMS,isomer #2	C[Si](C)(C)OCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1561.4	Standard non polar	33892256
L-Homoserine,3TMS,isomer #2	C[Si](C)(C)OCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1710.8	Standard polar	33892256
L-Homoserine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCO)N([Si](C)(C)C)[Si](C)(C)C	1556.8	Semi standard non polar	33892256
L-Homoserine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCO)N([Si](C)(C)C)[Si](C)(C)C	1509.5	Standard non polar	33892256
L-Homoserine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCO)N([Si](C)(C)C)[Si](C)(C)C	1650.2	Standard polar	33892256
L-Homoserine,4TMS,isomer #1	C[Si](C)(C)OCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1660.7	Semi standard non polar	33892256
L-Homoserine,4TMS,isomer #1	C[Si](C)(C)OCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1634.1	Standard non polar	33892256
L-Homoserine,4TMS,isomer #1	C[Si](C)(C)OCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1536.9	Standard polar	33892256
L-Homoserine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@H](N)C(=O)O	1555.2	Semi standard non polar	33892256
L-Homoserine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCO	1469.3	Semi standard non polar	33892256
L-Homoserine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCO)C(=O)O	1605.6	Semi standard non polar	33892256
L-Homoserine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1801.9	Semi standard non polar	33892256
L-Homoserine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCO[Si](C)(C)C(C)(C)C)C(=O)O	1871.4	Semi standard non polar	33892256
L-Homoserine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCO)C(=O)O[Si](C)(C)C(C)(C)C	1810.4	Semi standard non polar	33892256
L-Homoserine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCO)C(=O)O)[Si](C)(C)C(C)(C)C	1989.4	Semi standard non polar	33892256
L-Homoserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2092.9	Semi standard non polar	33892256
L-Homoserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2107.5	Standard non polar	33892256
L-Homoserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1979.7	Standard polar	33892256
L-Homoserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2247.4	Semi standard non polar	33892256
L-Homoserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2166.2	Standard non polar	33892256
L-Homoserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2041.0	Standard polar	33892256
L-Homoserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2219.6	Semi standard non polar	33892256
L-Homoserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2130.0	Standard non polar	33892256
L-Homoserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1998.5	Standard polar	33892256
L-Homoserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[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	2508.1	Semi standard non polar	33892256
L-Homoserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[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	2387.5	Standard non polar	33892256
L-Homoserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC[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	2050.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0v00-0930000000-3346aa2189b174721b86	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-MS (2 TMS)	splash10-0udj-1900000000-88ffce416068e87d5c9e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-MS (3 TMS)	splash10-0gdi-1960000000-b676faeb6cb80ca15570	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-EI-TOF (Non-derivatized)	splash10-0v00-0930000000-3346aa2189b174721b86	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-MS (Non-derivatized)	splash10-0udj-1900000000-88ffce416068e87d5c9e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-MS (Non-derivatized)	splash10-0gdi-1960000000-b676faeb6cb80ca15570	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-EI-TOF (Non-derivatized)	splash10-0gdi-0930000000-6216c27e0d6581b937aa	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-EI-TOF (Non-derivatized)	splash10-0udj-0900000000-d59a1b29c14ce935a8a2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homoserine GC-EI-TOF (Non-derivatized)	splash10-0ufv-0930000000-6efd3a5ade5c7320afb0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9100000000-d741144429bbc0c89fb2	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (2 TMS) - 70eV, Positive	splash10-0fk9-9530000000-9f3f4a1b429b17df7168	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homoserine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-9200000000-89f42491f91db334ecfc	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-d1859b3d67ed95698fa3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0abc-9100000000-eb77443ca02c8ccbe33a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-00di-0900000000-395a3c4889481d35a3f7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-00di-9300000000-634c194ce44ff0b3755f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-004i-9300000000-0c6e3c4dd011ef8c64fd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-000i-9000000000-d6e4f803999f61b58a6e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-00di-0900000000-45ed6aea7015ba6e6ca5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-00di-9400000000-30b57c9aabcc05806ce4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-0fk9-9400000000-74b23d9b0819343ff386	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-000i-9000000000-cde89cc67f5c874ed39c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-02t9-0891200000-72078b7028ff67e8adac	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0002-9000000000-178d6a086fe4d5123d31	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00kf-0900000000-1281df962d8640156255	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-02t9-0390000000-0afae0c03453d26542e6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-014i-0891100000-48060b947316dc631321	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0002-9000000000-3427ff1b0434696ae956	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-014i-0900000000-fd0f3bbc1a17c20a2475	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-03xr-0390000000-5a4fde017ce3426e8cd5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-00di-5900000000-a5903a71e92a78624d03	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-00di-9100000000-422851033dffe854f591	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0ab9-9000000000-cd7b70e1ead33d38a19f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0a4l-9000000000-481d61466b1d0af71cc2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-00di-9200000000-afddddfff24e50b7f835	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homoserine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0gb9-1900000000-89eb5226702ae527a2be	2012-08-31	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Methionine Metabolism
Cystathionine Beta-Synthase Deficiency		Not Available
Hypermethioninemia		Not Available
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency		Not Available
Glycine N-methyltransferase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	12.0 (11.3-17.0) uM	Adult (>18 years old)	Both	Normal	7067099	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.29 +/- 0.37 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	42.047 +/- 15.123 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	29.691 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
266600 (Crohn's disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB04193

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15699

Food Biomarker Ontology

Not Available

VMH ID

HOM_L

MarkerDB ID

MDB00000235

Good Scents ID

rw1253711

References

Synthesis Reference

Kokusenya, Yoshio; Matsuoka, Manabu. Synthesis of amino acids by electrochemical reduction. I. Synthesis of L-homoserine by electrochemical reduction of L-asparagine. Denki Kagaku oyobi Kogyo Butsuri Kagaku (1987), 55(2), 174-5.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Gazarian KG, Gening LV, Gazarian TG: L-Homoserine: a novel excreted metabolic marker of hepatitis B abnormally produced in liver from methionine. Med Hypotheses. 2002 Apr;58(4):279-83. [PubMed:12027520 ]
Compagnini A, Cunsolo V, Foti S, Saletti R: Improved accuracy in the matrix-assisted laser desorption/ionization-mass spectrometry determination of the molecular mass of cyanogen bromide fragments of proteins by post-cleavage reaction with tris(hydroxymethyl)aminomethane. Proteomics. 2001 Aug;1(8):967-74. [PubMed:11683513 ]

Showing metabocard for L-Homoserine (HMDB0000719)

MOL for HMDB0000719 (L-Homoserine)

3D MOL for HMDB0000719 (L-Homoserine)

3D SDF for HMDB0000719 (L-Homoserine)

3D-SDF for HMDB0000719 (L-Homoserine)

PDB for HMDB0000719 (L-Homoserine)

3D PDB for HMDB0000719 (L-Homoserine)

SMILES for HMDB0000719 (L-Homoserine)

INCHI for HMDB0000719 (L-Homoserine)

Structure for HMDB0000719 (L-Homoserine)

3D Structure for HMDB0000719 (L-Homoserine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra