L-Homoserine

Identification

Name
L-Homoserine
Accession Number
DB04193  (EXPT01782)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
6KA95X0IVO
CAS number
672-15-1
Weight
Average: 119.1192
Monoisotopic: 119.058243159
Chemical Formula
C4H9NO3
InChI Key
UKAUYVFTDYCKQA-VKHMYHEASA-N
InChI
InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1
IUPAC Name
(2S)-2-amino-4-hydroxybutanoic acid
SMILES
N[C@@H](CCO)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Methionine Adenosyltransferase DeficiencyDisease
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Disease
Threonine BiosynthesisMetabolic
Methionine MetabolismMetabolic
Cystathionine beta-Synthase DeficiencyDisease
Cysteine MetabolismMetabolic
Methionine MetabolismMetabolic
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDisease
Glycine N-Methyltransferase DeficiencyDisease
Secondary Metabolites: Threonine Biosynthesis from AspartateMetabolic
Threonine MetabolismMetabolic
Methionine MetabolismMetabolic
HypermethioninemiaDisease
Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation TypeDisease
Methionine BiosynthesisMetabolic
Methionine Metabolism and SalvageMetabolic
Threonine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

VItaly Arkadievich Livshits, Natalya Pavlovna Zakataeva, Vladimir Venyamiovich Aleoshin, Alla Valentinovna Balareova, Irina Lvovna Tokhmakova, "DNA coding for protein which confers on bacterium escherichia coli resistance to L-homoserine and method for producing L-amino acids." U.S. Patent US6303348, issued November, 1999.

US6303348
General References
Not Available
External Links
Human Metabolome Database
HMDB0000719
KEGG Compound
C00263
PubChem Compound
12647
PubChem Substance
46504898
ChemSpider
12126
ChEBI
15699
ChEMBL
CHEMBL11722
HET
HSE
PDB Entries
1ebu / 1h0g / 1h72 / 1j9n / 1pqp / 1w9u / 1waw / 2vdj / 3dks / 4c0j
show 6 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)203 dec °CPhysProp
water solubility1E+006 mg/L (at 30 °C)BEILSTEIN
Predicted Properties
PropertyValueSource
Water Solubility423.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.91 m3·mol-1ChemAxon
Polarizability11.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7439
Blood Brain Barrier-0.6081
Caco-2 permeable-0.7516
P-glycoprotein substrateNon-substrate0.7587
P-glycoprotein inhibitor INon-inhibitor0.9768
P-glycoprotein inhibitor IINon-inhibitor0.9883
Renal organic cation transporterNon-inhibitor0.9223
CYP450 2C9 substrateNon-substrate0.8202
CYP450 2D6 substrateNon-substrate0.8049
CYP450 3A4 substrateNon-substrate0.7865
CYP450 1A2 substrateNon-inhibitor0.8889
CYP450 2C9 inhibitorNon-inhibitor0.9394
CYP450 2D6 inhibitorNon-inhibitor0.9459
CYP450 2C19 inhibitorNon-inhibitor0.9574
CYP450 3A4 inhibitorNon-inhibitor0.9387
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9859
Ames testNon AMES toxic0.7826
CarcinogenicityNon-carcinogens0.9237
BiodegradationReady biodegradable0.959
Rat acute toxicity0.9205 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9766
hERG inhibition (predictor II)Non-inhibitor0.9525
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0v00-0930000000-3346aa2189b174721b86
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0udj-1900000000-88ffce416068e87d5c9e
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0gdi-1960000000-b676faeb6cb80ca15570
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0v00-0930000000-3346aa2189b174721b86
GC-MS Spectrum - GC-MSGC-MSsplash10-0udj-1900000000-88ffce416068e87d5c9e
GC-MS Spectrum - GC-MSGC-MSsplash10-0gdi-1960000000-b676faeb6cb80ca15570
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0gdi-0930000000-6216c27e0d6581b937aa
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udj-0900000000-d59a1b29c14ce935a8a2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ufv-0930000000-6efd3a5ade5c7320afb0
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-9200000000-89f42491f91db334ecfc
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a4i-9000000000-d1859b3d67ed95698fa3
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0abc-9100000000-eb77443ca02c8ccbe33a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-395a3c4889481d35a3f7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-9300000000-634c194ce44ff0b3755f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-9300000000-0c6e3c4dd011ef8c64fd
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-d6e4f803999f61b58a6e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-45ed6aea7015ba6e6ca5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-9400000000-30b57c9aabcc05806ce4
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0fk9-9400000000-74b23d9b0819343ff386
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-cde89cc67f5c874ed39c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-02t9-0891200000-72078b7028ff67e8adac
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-9000000000-178d6a086fe4d5123d31
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-00kf-0900000000-1281df962d8640156255
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-02t9-0390000000-0afae0c03453d26542e6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-014i-0891100000-48060b947316dc631321
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-9000000000-3427ff1b0434696ae956
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-014i-0900000000-fd0f3bbc1a17c20a2475
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03xr-0390000000-5a4fde017ce3426e8cd5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-00di-5900000000-a5903a71e92a78624d03
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-9100000000-422851033dffe854f591
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0ab9-9000000000-cd7b70e1ead33d38a19f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a4l-9000000000-481d61466b1d0af71cc2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00di-9200000000-afddddfff24e50b7f835
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0gb9-1900000000-89eb5226702ae527a2be
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-9000000000-178d6a086fe4d5123d31
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-9000000000-3427ff1b0434696ae956
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0900000000-fd0f3bbc1a17c20a2475
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0gb9-1900000000-89eb5226702ae527a2be
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-5900000000-a5903a71e92a78624d03
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9100000000-422851033dffe854f591
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-9000000000-cd7b70e1ead33d38a19f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4l-9000000000-481d61466b1d0af71cc2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-9300000000-634c194ce44ff0b3755f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-9300000000-0c6e3c4dd011ef8c64fd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-9400000000-30b57c9aabcc05806ce4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fk9-9400000000-74b23d9b0819343ff386
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-9200000000-afddddfff24e50b7f835
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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
Short-chain hydroxy acids and derivatives / Fatty acids and conjugates / 1,3-aminoalcohols / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Primary alcohols / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
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
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
homoserine (CHEBI:15699) / Other amino acids (C00263)

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:52