ECMDB: Homocysteine (ECMDB24053) (M2MDB006170)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)XML

Proteins (6)

Record Information

Version

2.0

Creation Date

2015-09-08 17:48:45 -0600

Update Date

2015-09-08 17:48:45 -0600

Secondary Accession Numbers

ECMDB24053

Identification

Name:

Homocysteine

Description

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Value	Source
2-Amino-4-mercaptobutyric acid	ChEBI
Hcy	ChEBI
2-Amino-4-mercaptobutyrate	Generator
(+-)-Homocysteine	HMDB
(S)-2-amino-4-mercapto-Butanoate	HMDB
(S)-2-amino-4-mercapto-Butanoic acid	HMDB
2-amino-4-mercapto-Butanoate	HMDB
2-amino-4-mercapto-Butanoic acid	HMDB
2-amino-4-mercapto-Butyric acid	HMDB
2-amino-4-mercapto-DL-Butyrate	HMDB
2-amino-4-mercapto-DL-Butyric acid	HMDB
2-amino-4-Sulfanylbutanoate	HMDB
2-amino-4-Sulfanylbutanoic acid	HMDB
D,L-Homocysteine	HMDB
DL-2-amino-4-mercapto-Butyric acid	HMDB
DL-2-amino-4-Mercaptobutyric acid	HMDB
DL-Homocysteine	HMDB
DL-Homocysteine (free base)	HMDB
homo-CYS	HMDB
L-2-amino-4-mercapto-Butyric acid	HMDB
L-Homocysteine	HMDB
Usaf b-12	HMDB
Homocysteine, L isomer	MeSH, HMDB
Homocysteine, L-isomer	MeSH, HMDB
2 amino 4 Mercaptobutyric acid	MeSH, HMDB
L-Isomer homocysteine	MeSH, HMDB

Chemical Formula:

C₄H₉NO₂S

Weight:

Average: 135.185
Monoisotopic: 135.035399227

InChI Key:

FFFHZYDWPBMWHY-UHFFFAOYSA-N

InChI:

InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)

CAS number:

Not Available

IUPAC Name:

2-amino-4-sulfanylbutanoic acid

Traditional IUPAC Name:

homocysteine

SMILES:

NC(CCS)C(O)=O

Chemical Taxonomy

Description

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfur-containing amino acid (CHEBI:17230 )
non-proteinogenic alpha-amino acid (CHEBI:17230 )
homocysteines (CHEBI:17230 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	14.8 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.6	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	2.46	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	32.94 m³·mol⁻¹	ChemAxon
Polarizability	13.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

5-Methyltetrahydrofolic acid + Homocysteine + 5-Methyltetrahydrofolic acid + Homocysteine > Tetrahydrofolic acid + L-Methionine + Tetrahydrofolic acid
Homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate + Homocysteine > L-Methionine + tetrahydropteroyltri-L-glutamate
L-Cystathionine > Hydrogen ion + Homocysteine + 2-aminoprop-2-enoate + Homocysteine
Homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate + Homocysteine > tetrahydropteroyltri-L-glutamate + L-Methionine
S-ribosyl-L-homocysteine + S-ribosyl-L-homocysteine > Homocysteine + autoinducer 2 + Homocysteine + autoinducer 2
Homocysteine + S-Methylmethionine <>2 L-Methionine + Hydrogen ion
S-ribosyl-L-homocysteine > 4,5-Dihydroxy-2,3-pentanedione + Homocysteine

SMPDB Pathways:

One Carbon Pool by Folate I	PW001735
Quorum Sensing	PW000836
S-adenosyl-L-methionine cycle	PW002080
methionine biosynthesis	PW000814

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0059-0930000000-b4e6d47b81f1810f1f31	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0910000000-7b3c5664e3b6b1930674	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0910000000-0dbe4ce28b468fb874f0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9730000000-952f5d413ee77e474820	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-03yi-3900000000-b5bcb65d1cfa2f5b4a83	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0059-1950000000-09d1f6d02198624082ea	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0059-0981000000-c6d399e1bddf1f7bc057	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0059-0930000000-b4e6d47b81f1810f1f31	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9730000000-952f5d413ee77e474820	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03yi-3900000000-b5bcb65d1cfa2f5b4a83	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0059-1950000000-09d1f6d02198624082ea	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-1f800d28bca4b2b7a49f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9700000000-368cb861e20b107da57a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9300000000-a8fd35730e901755194e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4l-9000000000-0e79cc37f5cb8f05cd37	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9000000000-694b412a6bed9a77958e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9700000000-2e1b7e55ed5da543b557	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-7e82906cac0f17bd5123	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9000000000-7c49d870f77950b940a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3900000000-4e1b7a42d769b9c2574c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-7900000000-35b3c5fd78dec88148fb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-533b0cacf1e578850e94	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17230
HMDB ID	Not Available
Pubchem Compound ID	778
Kegg ID	C05330
ChemSpider ID	Not Available
Wikipedia ID	Homocysteine
BioCyc ID	Not Available

Enzymes

Protein Details

1. Cystathionine beta-lyase metC

General function:: Involved in pyridoxal phosphate binding
Specific function:: L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate
Gene Name:: metC
Uniprot ID:: P06721
Molecular weight:: 43212

Reactions

L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.

Protein Details

2. Methionine synthase

General function:: Involved in methionine synthase activity
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
Gene Name:: metH
Uniprot ID:: P13009
Molecular weight:: 135996

Reactions

5-methyltetrahydrofolate + L-homocysteine = tetrahydrofolate + L-methionine.

Protein Details

3. Protein malY

General function:: Involved in transferase activity
Specific function:: Acts as a beta-cystathionase and as a repressor of the maltose regulon
Gene Name:: malY
Uniprot ID:: P23256
Molecular weight:: 43641

Reactions

L-cystathionine + H(2)O = L-homocysteine + NH(3) + pyruvate.

Protein Details

4. 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase

General function:: Involved in 5-methyltetrahydropteroyltriglutamate-homocysteine S-methyltransferase activity
Specific function:: Catalyzes the transfer of a methyl group from 5- methyltetrahydrofolate to homocysteine resulting in methionine formation
Gene Name:: metE
Uniprot ID:: P25665
Molecular weight:: 84673

Reactions

5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine.

Protein Details

5. S-ribosylhomocysteine lyase

General function:: Involved in catalytic activity
Specific function:: Involved in the synthesis of autoinducer 2 (AI-2) which is secreted by bacteria and is used to communicate both the cell density and the metabolic potential of the environment. The regulation of gene expression in response to changes in cell density is called quorum sensing. Catalyzes the transformation of S-ribosylhomocysteine (RHC) to homocysteine (HC) and 4,5- dihydroxy-2,3-pentadione (DPD)
Gene Name:: luxS
Uniprot ID:: P45578
Molecular weight:: 19416

Reactions

S-(5-deoxy-D-ribos-5-yl)-L-homocysteine = L-homocysteine + (4S)-4,5-dihydroxypentan-2,3-dione.

Protein Details

6. Homocysteine S-methyltransferase

General function:: Involved in homocysteine S-methyltransferase activity
Specific function:: Catalyzes methyl transfer from S-methylmethionine or S- adenosylmethionine (less efficient) to homocysteine, selenohomocysteine and less efficiently selenocysteine
Gene Name:: mmuM
Uniprot ID:: Q47690
Molecular weight:: 33422

Reactions

S-methyl-L-methionine + L-homocysteine = 2 L-methionine.

Homocysteine (ECMDB24053) (M2MDB006170)

Structure for #<Compound:0xa7778204>

Enzymes

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