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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:02 UTC
HMDB IDHMDB0000719
Secondary Accession Numbers
  • HMDB00719
Metabolite Identification
Common NameL-Homoserine
DescriptionHomoserine 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
Data?1582752152
Synonyms
ValueSource
(2S)-2-Amino-4-hydroxybutanoic acidChEBI
2-Amino-4-hydroxybutanoic acidChEBI
2-Amino-4-hydroxybutyric acidChEBI
HomoserineChEBI
(2S)-2-Amino-4-hydroxybutanoateGenerator
2-Amino-4-hydroxybutanoateGenerator
2-Amino-4-hydroxybutyrateGenerator
(S)-2-Amino-4-hydroxy-butanoateHMDB
(S)-2-Amino-4-hydroxy-butanoic acidHMDB
(S)-2-Amino-4-hydroxybutanoateHMDB
(S)-2-Amino-4-hydroxybutanoic acidHMDB
(S)-HomoserineHMDB
2-Amino-4-hydroxy-butyrateHMDB
2-Amino-4-hydroxy-butyric acidHMDB
2-Amino-4-hydroxy-L-butyrateHMDB
2-Amino-4-hydroxy-L-butyric acidHMDB
Homoserine L-isomerHMDB
L Isomer OF homoserineHMDB
L-Isomer OF homoserineHMDB
Chemical FormulaC4H9NO3
Average Molecular Weight119.1192
Monoisotopic Molecular Weight119.058243159
IUPAC Name(2S)-2-amino-4-hydroxybutanoic acid
Traditional NameL-homoserine
CAS Registry Number672-15-1
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 KeyUKAUYVFTDYCKQA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility423 g/LALOGPS
logP-3.3ALOGPS
logP-3.8ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)2.22ChemAxon
pKa (Strongest Basic)9.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.91 m³·mol⁻¹ChemAxon
Polarizability11.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available121.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002068
AllCCS[M+H]+ExperimentalNot Available126.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00002068
DarkChem[M+H]+PredictedNot Available125.81531661259
DarkChem[M-H]-PredictedNot Available120.20831661259
AllCCS[M+H]+PredictedNot Available129.08832859911
AllCCS[M-H]-PredictedNot Available122.16632859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
L-Homoserine,1TMS,#11313.9263https://arxiv.org/abs/1905.12712
L-Homoserine,1TMS,#21231.9253https://arxiv.org/abs/1905.12712
L-Homoserine,1TMS,#31350.8203https://arxiv.org/abs/1905.12712
L-Homoserine,2TMS,#11354.9496https://arxiv.org/abs/1905.12712
L-Homoserine,2TMS,#21426.7023https://arxiv.org/abs/1905.12712
L-Homoserine,2TMS,#31383.295https://arxiv.org/abs/1905.12712
L-Homoserine,2TMS,#41527.6823https://arxiv.org/abs/1905.12712
L-Homoserine,1TBDMS,#11555.2018https://arxiv.org/abs/1905.12712
L-Homoserine,1TBDMS,#21469.3472https://arxiv.org/abs/1905.12712
L-Homoserine,1TBDMS,#31605.6162https://arxiv.org/abs/1905.12712
L-Homoserine,2TBDMS,#11801.9473https://arxiv.org/abs/1905.12712
L-Homoserine,2TBDMS,#21871.384https://arxiv.org/abs/1905.12712
L-Homoserine,2TBDMS,#31810.375https://arxiv.org/abs/1905.12712
L-Homoserine,2TBDMS,#41989.4336https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0v00-0930000000-3346aa2189b174721b862014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udj-1900000000-88ffce416068e87d5c9e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gdi-1960000000-b676faeb6cb80ca155702014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0v00-0930000000-3346aa2189b174721b862017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udj-1900000000-88ffce416068e87d5c9e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gdi-1960000000-b676faeb6cb80ca155702017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gdi-0930000000-6216c27e0d6581b937aa2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-0900000000-d59a1b29c14ce935a8a22017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ufv-0930000000-6efd3a5ade5c7320afb02017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9100000000-d741144429bbc0c89fb22016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fk9-9530000000-9f3f4a1b429b17df71682017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9100000000-3c5ae1e5b01441b7feac2021-09-05View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9200000000-89f42491f91db334ecfc2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-d1859b3d67ed95698fa32012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0abc-9100000000-eb77443ca02c8ccbe33a2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-395a3c4889481d35a3f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9300000000-634c194ce44ff0b3755f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-9300000000-0c6e3c4dd011ef8c64fd2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-d6e4f803999f61b58a6e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-45ed6aea7015ba6e6ca52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9400000000-30b57c9aabcc05806ce42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0fk9-9400000000-74b23d9b0819343ff3862012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-cde89cc67f5c874ed39c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-02t9-0891200000-72078b7028ff67e8adac2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9000000000-178d6a086fe4d5123d312012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00kf-0900000000-1281df962d86401562552012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-02t9-0390000000-0afae0c03453d26542e62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-0891100000-48060b947316dc6313212012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9000000000-3427ff1b0434696ae9562012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-0900000000-fd0f3bbc1a17c20a24752012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03xr-0390000000-5a4fde017ce3426e8cd52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-5900000000-a5903a71e92a78624d032012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9100000000-422851033dffe854f5912012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0ab9-9000000000-cd7b70e1ead33d38a19f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4l-9000000000-481d61466b1d0af71cc22012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-9200000000-afddddfff24e50b7f8352012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0gb9-1900000000-89eb5226702ae527a2be2012-08-31View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)2015-03-12View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (predicted)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.0 (11.3-17.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.29 +/- 0.37 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified42.047 +/- 15.123 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified29.691 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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
  1. 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
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB04193
Phenol Explorer Compound IDNot Available
FooDB IDFDB006683
KNApSAcK IDC00001366
Chemspider ID12126
KEGG Compound IDC00263
BioCyc IDHOMO-SER
BiGG ID34437
Wikipedia LinkHomoserine
METLIN ID5687
PubChem Compound12647
PDB IDNot Available
ChEBI ID15699
Food Biomarker OntologyNot Available
VMH IDHOM_L
MarkerDB IDMDB00000235
References
Synthesis ReferenceKokusenya, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]