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Showing metabocard for Homocysteine (BMDB0000742)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:50 UTC
Update Date2020-05-21 16:28:33 UTC
BMDB IDBMDB0000742
Secondary Accession Numbers
  • BMDB00742
Metabolite Identification
Common NameHomocysteine
DescriptionHomocysteine, also known as Hcy or homo-cys, 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). Homocysteine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Homocysteine exists in all living species, ranging from bacteria to humans. Homocysteine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HcyChEBI
L-2-Amino-4-mercaptobutyric acidChEBI
L-2-Amino-4-mercaptobutyrateGenerator
2-Amino-4-mercaptobutyric acidHMDB
Homocysteine, L isomerHMDB
L-Isomer homocysteineHMDB
2 Amino 4 mercaptobutyric acidHMDB
Homocysteine, L-isomerHMDB
(S)-2-Amino-4-mercapto-butanoateHMDB
(S)-2-Amino-4-mercapto-butanoic acidHMDB
(S)-2-Amino-4-mercaptobutanoic acidHMDB
(S)-HomocysteineHMDB
2-Amino-4-mercapto-DL-butyrateHMDB
2-Amino-4-mercapto-DL-butyric acidHMDB
2-Amino-4-mercapto-L-butyric acidHMDB
2-Amino-4-mercapto-butanoateHMDB
2-Amino-4-mercapto-butanoic acidHMDB
2-Amino-4-mercapto-butyric acidHMDB
2-Amino-4-sulfanylbutanoateHMDB
2-Amino-4-sulfanylbutanoic acidHMDB
D,L-HomocysteineHMDB
DL-2-Amino-4-mercapto-butyric acidHMDB
DL-2-Amino-4-mercaptobutyric acidHMDB
DL-HomocysteineHMDB
Homo-cysHMDB
L-2-Amino-4-mercapto-butyric acidHMDB
L-HomocysteineHMDB
2-Amino-4-mercapto-butyrateHMDB
HomocysteineMeSH, KEGG
Chemical FormulaC4H9NO2S
Average Molecular Weight135.185
Monoisotopic Molecular Weight135.035399227
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number454-29-5
SMILESNot Available
InChI Identifier
InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1
InChI KeyFFFHZYDWPBMWHY-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
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point232 - 233 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility148 mg/mLNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adipose Tissue
  • Brain
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Milk
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000742
DrugBank IDDB04422
Phenol Explorer Compound IDNot Available
FooDB IDFDB001491
KNApSAcK IDC00001365
Chemspider ID82666
KEGG Compound IDC00155
BioCyc IDHOMO-CYS
BiGG IDNot Available
Wikipedia LinkHomocysteine
METLIN ID3256
PubChem Compound91552
PDB IDNot Available
ChEBI ID17588
References
Synthesis ReferenceKarrenbauer, Michael; Kleemann, Axel; Luessling, Theodor; Schaefer, Fritz. D,L-Homocysteine (I). Ger. (1984), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Enzymes

Enzyme Details
1. Methionine synthase
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q4JIJ3
Molecular weight:
140478.0
Reactions
Homocysteine + 5-Methyltetrahydrofolic acid → L-Methionine + Tetrahydrofolic aciddetails
Enzyme Details
2. Adenosylhomocysteinase
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
AHCYL1
Uniprot ID:
A5PKK6
Molecular weight:
68585.0
Enzyme Details
3. Adenosylhomocysteinase 3
General function:
Coenzyme transport and metabolism
Specific function:
May regulate the electrogenic sodium/bicarbonate cotransporter SLC4A4 activity and Mg(2+)-sensitivity. On the contrary of its homolog AHCYL1, does not regulate ITPR1 sensitivity to inositol 1,4,5-trisphosphate (By similarity).
Gene Name:
AHCYL2
Uniprot ID:
A6QLP2
Molecular weight:
66774.0
Enzyme Details
4. Betaine--homocysteine S-methyltransferase 1
General function:
Amino acid transport and metabolism
Specific function:
Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline (By similarity).
Gene Name:
BHMT
Uniprot ID:
Q5I597
Molecular weight:
44878.0
Reactions
Betaine + Homocysteine → Dimethylglycine + L-Methioninedetails
L-Cystathionine → Homocysteinedetails
Enzyme Details
5. Adenosylhomocysteinase
General function:
Coenzyme transport and metabolism
Specific function:
Adenosylhomocysteine is a competitive inhibitor of S-adenosyl-L-methionine-dependent methyl transferase reactions; therefore adenosylhomocysteinase may play a key role in the control of methylations via regulation of the intracellular concentration of adenosylhomocysteine.
Gene Name:
AHCY
Uniprot ID:
Q3MHL4
Molecular weight:
47638.0
Reactions
S-Adenosylhomocysteine + Water → Homocysteine + Adenosinedetails
Enzyme Details
6. Cystathionine beta-synthase
General function:
Not Available
Specific function:
Not Available
Gene Name:
CBS
Uniprot ID:
F1MEW4
Molecular weight:
62867.0
Reactions
Homocysteine + L-Serine → Water + L-Cystathioninedetails