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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:41 UTC

Update Date

2023-02-21 17:16:15 UTC

HMDB ID

HMDB0002205

Secondary Accession Numbers

HMDB02205

Metabolite Identification

Common Name

L-Homocysteic acid

Description

L-homocysteic acid is a homocysteic acid with L-configuration. It has a role as a NMDA receptor agonist. It is an enantiomer of a D-homocysteic acid. L-Homocysteic acid is a sulfur-containing glutamic acid analog and a potent NMDA receptor agonist. It is related to homocysteine, a by-product of methionine metabolism. It 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.

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-sulfobutyric acid	ChEBI
(S)-2-Amino-4-sulfobutanoic acid	ChEBI
(S)-2-Amino-4-sulfobutyric acid	ChEBI
Homocysteic acid	ChEBI
L-2-Amino-4-sulfobutyric acid	ChEBI
(2S)-2-Amino-4-sulfobutanoic acid	Kegg
(2S)-2-Amino-4-sulfobutyrate	Generator
(2S)-2-Amino-4-sulphobutyrate	Generator
(2S)-2-Amino-4-sulphobutyric acid	Generator
(S)-2-Amino-4-sulfobutanoate	Generator
(S)-2-Amino-4-sulphobutanoate	Generator
(S)-2-Amino-4-sulphobutanoic acid	Generator
(S)-2-Amino-4-sulfobutyrate	Generator
(S)-2-Amino-4-sulphobutyrate	Generator
(S)-2-Amino-4-sulphobutyric acid	Generator
Homocysteate	Generator
L-2-Amino-4-sulfobutyrate	Generator
L-2-Amino-4-sulphobutyrate	Generator
L-2-Amino-4-sulphobutyric acid	Generator
(2S)-2-Amino-4-sulfobutanoate	Generator
(2S)-2-Amino-4-sulphobutanoate	Generator
(2S)-2-Amino-4-sulphobutanoic acid	Generator
L-Homocysteate	Generator

Chemical Formula

C₄H₉NO₅S

Average Molecular Weight

183.183

Monoisotopic Molecular Weight

183.020143093

IUPAC Name

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

Traditional Name

L-homocysteic acid

CAS Registry Number

14857-77-3

SMILES

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

InChI Identifier

InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1

InChI Key

VBOQYPQEPHKASR-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
Thia fatty acid
Fatty acid
Fatty acyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:80543 )

Ontology

Not Available

Endogenous (HMDB: HMDB0002205)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	261 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	140.3	30932474
[M-H]-	Not Available	125.847	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000051
[M+H]+	Not Available	140.37	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000051

Predicted Molecular Properties

Property	Value	Source
Water Solubility	64.3 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.9	ChemAxon
logS	-0.45	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.3 m³·mol⁻¹	ChemAxon
Polarizability	15.69 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]+	140.726	31661259
DarkChem	[M-H]-	134.802	31661259
DeepCCS	[M+H]+	135.469	30932474
DeepCCS	[M-H]-	131.896	30932474
DeepCCS	[M-2H]-	169.401	30932474
DeepCCS	[M+Na]+	144.94	30932474
AllCCS	[M+H]+	139.3	32859911
AllCCS	[M+H-H2O]+	135.5	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	143.9	32859911
AllCCS	[M-H]-	130.5	32859911
AllCCS	[M+Na-2H]-	132.4	32859911
AllCCS	[M+HCOO]-	134.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Homocysteic acid	N[C@@H](CCS(O)(=O)=O)C(O)=O	2656.4	Standard polar	33892256
L-Homocysteic acid	N[C@@H](CCS(O)(=O)=O)C(O)=O	1294.6	Standard non polar	33892256
L-Homocysteic acid	N[C@@H](CCS(O)(=O)=O)C(O)=O	2093.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Homocysteic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O	1751.5	Semi standard non polar	33892256
L-Homocysteic acid,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)CC[C@H](N)C(=O)O	1840.0	Semi standard non polar	33892256
L-Homocysteic acid,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O	1772.9	Semi standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O[Si](C)(C)C	1823.9	Semi standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O[Si](C)(C)C	1897.8	Standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O[Si](C)(C)C	2948.5	Standard polar	33892256
L-Homocysteic acid,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O[Si](C)(C)C	1830.3	Semi standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O[Si](C)(C)C	1919.7	Standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O[Si](C)(C)C	2850.5	Standard polar	33892256
L-Homocysteic acid,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C)C(=O)O	1905.8	Semi standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C)C(=O)O	1880.9	Standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C)C(=O)O	2717.6	Standard polar	33892256
L-Homocysteic acid,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCS(=O)(=O)O)C(=O)O)[Si](C)(C)C	1955.3	Semi standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCS(=O)(=O)O)C(=O)O)[Si](C)(C)C	1984.7	Standard non polar	33892256
L-Homocysteic acid,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCS(=O)(=O)O)C(=O)O)[Si](C)(C)C	3038.8	Standard polar	33892256
L-Homocysteic acid,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1924.3	Semi standard non polar	33892256
L-Homocysteic acid,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2056.3	Standard non polar	33892256
L-Homocysteic acid,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2367.4	Standard polar	33892256
L-Homocysteic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1995.0	Semi standard non polar	33892256
L-Homocysteic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2144.2	Standard non polar	33892256
L-Homocysteic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2604.7	Standard polar	33892256
L-Homocysteic acid,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2030.8	Semi standard non polar	33892256
L-Homocysteic acid,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2126.1	Standard non polar	33892256
L-Homocysteic acid,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2503.3	Standard polar	33892256
L-Homocysteic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2067.5	Semi standard non polar	33892256
L-Homocysteic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2272.2	Standard non polar	33892256
L-Homocysteic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2292.7	Standard polar	33892256
L-Homocysteic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O	2016.0	Semi standard non polar	33892256
L-Homocysteic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)CC[C@H](N)C(=O)O	2080.0	Semi standard non polar	33892256
L-Homocysteic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O	2029.5	Semi standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O[Si](C)(C)C(C)(C)C	2291.6	Semi standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O[Si](C)(C)C(C)(C)C	2464.3	Standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCS(=O)(=O)O[Si](C)(C)C(C)(C)C	2940.6	Standard polar	33892256
L-Homocysteic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2288.3	Semi standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2455.1	Standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2846.6	Standard polar	33892256
L-Homocysteic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2386.7	Semi standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2442.7	Standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2734.6	Standard polar	33892256
L-Homocysteic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCS(=O)(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2417.0	Semi standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCS(=O)(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2492.2	Standard non polar	33892256
L-Homocysteic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCS(=O)(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2947.0	Standard polar	33892256
L-Homocysteic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2566.9	Semi standard non polar	33892256
L-Homocysteic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2874.9	Standard non polar	33892256
L-Homocysteic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2604.0	Standard polar	33892256
L-Homocysteic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2675.6	Semi standard non polar	33892256
L-Homocysteic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2916.8	Standard non polar	33892256
L-Homocysteic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2733.3	Standard polar	33892256
L-Homocysteic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2711.9	Semi standard non polar	33892256
L-Homocysteic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2922.8	Standard non polar	33892256
L-Homocysteic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2665.0	Standard polar	33892256
L-Homocysteic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2918.9	Semi standard non polar	33892256
L-Homocysteic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3326.2	Standard non polar	33892256
L-Homocysteic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2590.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocysteic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-9200000000-227327e2ea07b407a345	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocysteic acid GC-MS (1 TMS) - 70eV, Positive	splash10-000i-6900000000-31638e5ec109cfafd44e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocysteic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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-Homocysteic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0019-1900000000-9e519a1dc69bad6b052a	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homocysteic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-0969185dbffad2caca30	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homocysteic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-6000560b5af6914a56f3	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 10V, Positive-QTOF	splash10-00li-0900000000-14ffff3301fb95818ba1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 20V, Positive-QTOF	splash10-0a4r-4900000000-937b06eba260edf97366	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 40V, Positive-QTOF	splash10-0a4i-9300000000-adb2ff0a0fa33a9254c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 10V, Negative-QTOF	splash10-001i-3900000000-850821a58ef9d7da6dd0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 20V, Negative-QTOF	splash10-001i-9500000000-56e02bca51cc72bc4c65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 40V, Negative-QTOF	splash10-001i-9000000000-c4b654f035544d07c77e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 10V, Positive-QTOF	splash10-052r-2900000000-582366e5c041b3a0c9e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 20V, Positive-QTOF	splash10-0a4i-9200000000-ab6b416d6b40d5adca0d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-a84ce26c9131a9e0222a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 10V, Negative-QTOF	splash10-03e9-0900000000-88837f57ed9e6288ce19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 20V, Negative-QTOF	splash10-001i-9300000000-9ef50dfa13539152f167	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocysteic acid 40V, Negative-QTOF	splash10-001i-9000000000-a6fb8cd4d3dc149be309	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022905

KNApSAcK ID

Not Available

Chemspider ID

154529

KEGG Compound ID

C16511

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Homocysteic_acid

METLIN ID

6545

PubChem Compound

177491

PDB ID

Not Available

ChEBI ID

132223

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Jolles-Bergeret, Bernadette. Synthesis and properties of L- and DL-homocysteine sulfinic and L-homocysteic acids. Bulletin de la Societe de Chimie Biologique (1966), 48(11), 1265-78.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Boldyrev AA: Homocysteinic acid causes oxidative stress in lymphocytes by potentiating toxic effect of NMDA. Bull Exp Biol Med. 2005 Jul;140(1):33-7. [PubMed:16254614 ]
Piraud M, Vianey-Saban C, Bourdin C, Acquaviva-Bourdain C, Boyer S, Elfakir C, Bouchu D: A new reversed-phase liquid chromatographic/tandem mass spectrometric method for analysis of underivatised amino acids: evaluation for the diagnosis and the management of inherited disorders of amino acid metabolism. Rapid Commun Mass Spectrom. 2005;19(22):3287-97. [PubMed:16235234 ]

Showing metabocard for L-Homocysteic acid (HMDB0002205)

MOL for HMDB0002205 (L-Homocysteic acid)

3D MOL for HMDB0002205 (L-Homocysteic acid)

3D SDF for HMDB0002205 (L-Homocysteic acid)

3D-SDF for HMDB0002205 (L-Homocysteic acid)

PDB for HMDB0002205 (L-Homocysteic acid)

3D PDB for HMDB0002205 (L-Homocysteic acid)

SMILES for HMDB0002205 (L-Homocysteic acid)

INCHI for HMDB0002205 (L-Homocysteic acid)

Structure for HMDB0002205 (L-Homocysteic acid)

3D Structure for HMDB0002205 (L-Homocysteic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra