MiMeDB: Showing metabocard for L-Homocysteine (MMDBc0029477)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:23:53 UTC

Update Date

2024-04-20 06:12:33 UTC

Metabolite ID

MMDBc0029477

Metabolite Identification

Common Name

L-Homocysteine

Description

Homocysteine is a thiol-containing amino acid formed by a demethylation of methionine. Homocysteine is a variant of the amino acid cysteine, differing in that its side-chain contains an additional methylene (-CH2-) group before the thiol (-SH) group. In Escherichia coli homocysteine (Hcy) is the last intermediate on the methionine biosynthetic pathway.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
Hcy	ChEBI
L-2-Amino-4-mercaptobutyric acid	ChEBI
L-2-Amino-4-mercaptobutyrate	Generator
2-Amino-4-mercaptobutyric acid	HMDB
Homocysteine, L isomer	HMDB
L-Isomer homocysteine	HMDB
2 Amino 4 mercaptobutyric acid	HMDB
Homocysteine, L-isomer	HMDB
(S)-2-Amino-4-mercapto-butanoate	HMDB
(S)-2-Amino-4-mercapto-butanoic acid	HMDB
(S)-2-Amino-4-mercaptobutanoic acid	HMDB
(S)-Homocysteine	HMDB
2-Amino-4-mercapto-DL-butyrate	HMDB
2-Amino-4-mercapto-DL-butyric acid	HMDB
2-Amino-4-mercapto-L-butyric 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-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
Homo-cys	HMDB
L-2-Amino-4-mercapto-butyric acid	HMDB
L-Homocysteine	HMDB
2-Amino-4-mercapto-butyrate	HMDB
Homocysteine	MeSH, KEGG

Molecular Formula

C₄H₉NO₂S

Average Mass

135.185

Monoisotopic Mass

135.035399227

IUPAC Name

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

Traditional Name

L-homocysteine

CAS Registry Number

6027-13-0

SMILES

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

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 Key

FFFHZYDWPBMWHY-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
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 Framework

Aliphatic acyclic compounds

External Descriptors

homocysteine (CHEBI:17588 )
serine family amino acid (CHEBI:17588 )
Other amino acids (C00155 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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	13.54 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0920000000-20fbffbe76510c066e6f	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-1f800d28bca4b2b7a49f	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014l-4900000000-c50d79ba3a5013bcf29f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-025c9e1f4fb58138c43b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-4900000000-33f205e002f49f034764	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052r-0900000000-c1f98c8182b5ddc09cb1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ko-9800000000-80a1c80328e8836233a4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-1f611da44349ffdfaefe	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9000000000-c9d62a66522e46a17f56	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3900000000-e8322d5858cba16a3bd2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-6900000000-e0190a1cc33e605bac0a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-900bb5d8fb11bec02e39	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-38e427e24202b2411597	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-7900000000-5cf2133d9faac56032d3	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-166428542631f9ac0714	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9bcb57b924579a6c3411	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-8eee886864db64f3eec2	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2019-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)		2019-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2019-05-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2019-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2019-05-22	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Blood
Brain
Cerebrospinal Fluid (CSF)
Feces
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Saliva
Skeletal Muscle
Urine

Tissue Locations

Adipose Tissue
Brain
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191831	Methionine synthase	Unknown	Q99707	Homo sapiens
MMDBp0192205	Betaine--homocysteine S-methyltransferase 1	Unknown	Q93088	Homo sapiens
MMDBp0192301	Putative adenosylhomocysteinase 3	Unknown	Q96HN2	Homo sapiens
MMDBp0192302	Adenosylhomocysteinase	Unknown	P23526	Homo sapiens
MMDBp0192303	Putative adenosylhomocysteinase 2	Unknown	O43865	Homo sapiens
MMDBp0192399	Cystathionine beta-synthase	Unknown	P35520	Homo sapiens
MMDBp0193964	S-methylmethionine--homocysteine S-methyltransferase BHMT2	Unknown	Q9H2M3	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013270	Water	L-Homocysteine	L-alanine/L-glutamate racemase	Non-hydrolytic bond cleavage (or its reversal); Racemization	RHEA	34755880
MMDBr0013271	Water	L-Homocysteine	Cysteine-S-conjugate beta-lyase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0013320	Water	2-oxobutanoic acid	Cystathionine gamma-lyase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0013683	S-Ribosyl-L-homocysteine	(4S)-4,5-Dihydroxypentan-2,3-dione	S-ribosylhomocysteine lyase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0014135	Water	Deoxyadenosine	Adenosylhomocysteinase	Reversible hydrolysis	RHEA	34755880
MMDBr0014737	Hydrogen sulfide	Acetic acid	Cystathionine gamma-synthase/O-acetylhomoserine (thiol)-lyase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0014738	Hydrogen sulfide	Acetic acid	O-acetyl-L-homoserine sulfhydrylase	Sulfhydrylase	RHEA	34755880
MMDBr0014739	Hydrogen sulfide	L-Homocysteine	O-succinylhomoserine sulfhydrylase	Sulfhydrylase	RHEA	34755880
MMDBr0015174	L-Homocysteine	Acetic acid	O-acetylserine dependent cystathionine beta-synthase	Synthesis	RHEA	34755880
MMDBr0017022	Water	Inosine	S-inosyl-L-homocysteine hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0017023	Water	Inosine	S-inosyl-L-homocysteine hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0017831	L-Homocysteine	Water	Cystathionine beta-synthase	Synthesis	RHEA	34755880
MMDBr0017838	(6S)-5-methyl-5,6,7,8-tetrahydrofolic acid	(6S)-5,6,7,8-tetrahydrofolic acid	Methionine synthase	Synthesis	RHEA	34755880
MMDBr0017898	5-methyltetrahydropteroyltri-L-glutamate	L-Methionine	5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase	Methylation	RHEA	34755880
MMDBr0017899	5-methyltetrahydropteroyltri-L-glutamate	L-Methionine	Probable 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase	Methylation	RHEA	34755880
MMDBr0017924	L-Homocysteine	Hydrogen Ion	Homocysteine S-methyltransferase YbgG	Methylation; Reduction	RHEA	34755880
MMDBr0025660	Hydrogen Ion	Water	L-aspartate semialdehyde sulfurtransferase	Sulfuration	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	16227558
Alzheimer's disease	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	21474939
Alzheimer's disease	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11959400
Amyotrophic lateral sclerosis	Slight Increase	Association	Human Blood	HMDB	20606437
Creutzfeldt-jakob disease	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	15711082
Creutzfeldt-jakob disease	Slight Decrease	Association	Human Blood	HMDB	15711082
Cystathioninuria		Association	Human Blood	HMDB	20584029
Dementia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	17384003
Dementia	Slight Increase	Association	Human Blood	HMDB	17384003
Dimethylglycine dehydrogenase deficiency		Association	Human Blood	HMDB	10102904
Multiple sclerosis		Association	Human Cerebrospinal Fluid (CSF)	HMDB	17384003
Multiple sclerosis		Association	Human Blood	HMDB	17384003
Parkinson's disease	Increased	Association	Human Blood	HMDB	20606437
Peripheral neuropathy		Association	Human Cerebrospinal Fluid (CSF)	HMDB	17384003
Peripheral neuropathy	Slight Increase	Association	Human Blood	HMDB	17384003
Progressive supranuclear palsy	Slight Increase	Association	Human Blood	HMDB	20606437
Sickle cell anemia	Slight Increase	Association	Human Blood	HMDB	9798656
Stroke		Association	Human Cerebrospinal Fluid (CSF)	HMDB	17384003
Stroke		Association	Human Blood	HMDB	17384003
Transcobalamin ii deficiency		Association	Human Urine	HMDB	10518276
Uremia	Increased	Association	Human Blood	HMDB	12675874
Uremia	Increased	Association	Human Blood	HMDB	22626821
Homocystinuria	Increased	Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Homocystinuria	Decreased	Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	454	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Cattle ; River trout ; Lion ; Chicken ; Rat ; Sheep ; Turkey	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	458	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Catfish	Metabolic reconstruction
Bacteria	Actinobacteria	149	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	122	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	11	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	6	Human feces; Human saliva	Unknown
Bacteria	Deinococcus-thermus	5
Eukaryota/Fungi	Basidiomycota	1
Bacteria	Thermotogae	3
Bacteria/NULL	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Cattle ; River trout ; Lion ; Chicken ; Rat ; Sheep ; Turkey	Unknown; Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	4		Metabolic reconstruction
Bacteria	Aquificae	1
Archaea/Archaea	Euryarchaeota	16		Metabolic reconstruction
Bacteria	Chlorobi	8
Bacteria	Cyanobacteria	19
Archaea	Euryarchaeota	1
Bacteria	Acidobacteria	1
Bacteria	nah	1
Bacteria	Chloroflexi	1
Bacteria	Nitrospirae	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.12	0.062			uM	Elderly (>65 years old)	Not Specified	Alzheimer's disease	HMDB	16227558
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.216	0.122			uM	Adult (>18 years old)	Not Specified	Alzheimer's disease	HMDB	21474939
Human Cerebrospinal fluid (csf)	Detected and Quantified	14.2	1.7			uM	Elderly (>65 years old)	Not Specified	Alzheimer's disease	HMDB	11959400
Human Blood	Detected and Quantified	13.94	3.47			uM	Adult (>18 years old)	Both	Amyotrophic lateral sclerosis	HMDB	20606437
Human Blood	Detected and Quantified	21.0		18.5	25.7	uM	Adult (>18 years old)	Both	Chronic renal failure	HMDB	11380830
Human Blood	Detected and Quantified	25.5		16.9	32.6	uM	Adult (>18 years old)	Both	Continuous ambulatory peritoneal dialysis (CAPD)	HMDB	11380830
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.13	0.03			uM	Adult (>18 years old)	Not Specified	Cruetzfeldt-Jakob disease	HMDB	15711082
Human Blood	Detected and Quantified	9.22	1.81			uM	Adult (>18 years old)	Not Specified	Cruetzfeldt-Jakob disease	HMDB	15711082
Human Blood	Detected and Quantified	3.5				uM	Children (1-13 years old)	Female	Cystathioninuria	HMDB	20584029
Human Blood	Detected and Quantified	19				uM	Children (1-13 years old)	Female	Cystathioninuria	HMDB	20584029
Human Blood	Detected and Quantified	20.5				uM	Children (1-13 years old)	Female	Cystathioninuria	HMDB	20584029
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.10	0.06‚Äì0.32			uM	Adult (>18 years old)	Not Specified	Dementia (Alzheimer's and non-Alzheimer's)	HMDB	17384003
Human Blood	Detected and Quantified	12.9		8.2	28.2	uM	Adult (>18 years old)	Not Specified	Dementia (Alzheimer's and non-Alzheimer's)	HMDB	17384003
Human Blood	Detected and Quantified	12				uM	Adult (>18 years old)	Male	Dimethylglycinuria	HMDB	10102904
Human Blood	Detected and Quantified	29.7		25.7	38.2	uM	Adult (>18 years old)	Both	Hemodialysis	HMDB	11380830
Human Blood	Detected and Quantified	180				uM	Adult (>18 years old)	Male	Methylenetetrahydrofolate reductase deficiency	HMDB	8456826
Human Blood	Detected and Quantified	0.9				uM	Children (1-13 years old)	Male	Molybdenium co-factor deficiency	HMDB	26644055
Human Blood	Detected and Quantified	<1.000				uM	Newborn (0-30 days old)	Female	Molybdenum cofactor deficiency	HMDB	12872846
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.08		0.05	0.16	uM	Adult (>18 years old)	Not Specified	Multiple sclerosis	HMDB	17384003
Human Blood	Detected and Quantified	10.7		7.6	14.4	uM	Adult (>18 years old)	Not Specified	Multiple sclerosis	HMDB	17384003
Human Blood	Detected and Quantified	15.1				uM	Adult (>18 years old)	Both	Parkinson's disease	HMDB	20606437
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.11		0.07	0.18	uM	Adult (>18 years old)	Not Specified	Peripheral neuropathy	HMDB	17384003
Human Blood	Detected and Quantified	11.9		7.0	19.1	uM	Adult (>18 years old)	Not Specified	Peripheral neuropathy	HMDB	17384003
Human Blood	Detected and Quantified	15.75	5.75			uM	Adult (>18 years old)	Both	Progressive supranuclear palsy	HMDB	20606437
Human Blood	Detected and Quantified	12.5	5.0			uM	Adult (>18 years old)	Both	Sickle cell anemia	HMDB	9798656
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.08		0.06	0.15	uM	Adult (>18 years old)	Not Specified	Stroke	HMDB	17384003
Human Blood	Detected and Quantified	10.2		7.0	17.4	uM	Adult (>18 years old)	Not Specified	Stroke	HMDB	17384003
Human Urine	Detected and Quantified			0.470	0.500	umol/mmol creatinine	Newborn (0-30 days old)	Female	Transcobalamin II deficiency	HMDB	10518276
Human Blood	Detected and Quantified	60	11.852			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	68.80	15.53			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified			3	8	uM	Newborn (0-30 days old)	Both	Normal	HMDB	12872846
Human Blood	Detected and Quantified			4	12	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	26644055
Human Blood	Detected and Quantified			8	18	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	10102904
Human Blood	Detected and Quantified	<12.593				uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Blood	Detected and Quantified	<20				uM	Adult (>18 years old)	Both	Normal	HMDB	8456826
Human Blood	Detected and Quantified	<7.500				uM	Not Specified	Not Specified	Normal	HMDB	23430506
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.057	0.035			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16227558
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.09		0.06	0.16	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	17384003
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.12	0.08			uM	Elderly (>65 years old)	Not Specified	Normal	HMDB	16227558
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.15	0.07			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15711082
Human Urine	Detected and Quantified			0.86	1.2	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.91	1.4	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.1		0.6	1.74	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	1.5	0.69			umol/mmol creatinine	Children (1-13 years old)	Male	Normal	HMDB	9554495
Human Urine	Detected and Quantified	1.78	0.73			umol/mmol creatinine	Adolescent (13-18 years old)	Male	Normal	HMDB	9554495
Human Urine	Detected and Quantified	1.95	1.47			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	9554495
Human Blood	Detected and Quantified	10.4	2.3			uM	Children (1-13 years old)	Both	Normal	HMDB	9554495
Human Blood	Detected and Quantified	10.900	2.800			uM	Adult (>18 years old)	Both	Normal	HMDB	17521468
Human Blood	Detected and Quantified	11.600	3			uM	Adult (>18 years old)	Both	Normal	HMDB	17521468
Human Blood	Detected and Quantified	12.600	3.100			uM	Adult (>18 years old)	Both	Normal	HMDB	17521468
Human Blood	Detected and Quantified	13.300	2.900			uM	Adult (>18 years old)	Both	Normal	HMDB	17521468
Human Urine	Detected and Quantified	2.00	1.65			umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	9554495
Human Cerebrospinal fluid (csf)	Detected and Quantified	20.7	1.7			uM	Elderly (>65 years old)	Both	Normal	HMDB	11959400
Human Blood	Detected and Quantified	5.00	1.6			uM	Infant (0-1 year old)	Both	Normal	HMDB	9554495
Human Blood	Detected and Quantified	5.600	1.200			uM	Adult (>18 years old)	Female	Normal	HMDB	12891147
Human Saliva	Detected and Quantified	6.6	8.0			uM	Adult (>18 years old)	Both	Normal	HMDB	24261982
Human Blood	Detected and Quantified	9.00	2.00			uM	Adult (>18 years old)	Both	Normal	HMDB	9554495
Human Blood	Detected and Quantified	9.00	2.2			uM	Adolescent (13-18 years old)	Both	Normal	HMDB	9554495
Human Blood	Detected and Quantified	9.11	2.99			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15711082
Human Blood	Detected and Quantified	9.4		7.3	16.2	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	17384003
Human Blood	Detected and Quantified	9.8		7.6	14.9	uM	Adult (>18 years old)	Both	Normal	HMDB	11380830
Human Blood	Detected and Quantified	9.99	1.04			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Blood	Detected and Quantified	<0.700				uM	Infant (0-1 year old)	Male	Sulfite oxidase deficiency	HMDB	Clinical and Laboratory Barriers to the Timely Diagnosis of Sulphite Oxidase Deficiency. Proceedings of Singapore Healthcare, 19(2), 94-100.
Human Blood	Detected and Quantified	125.00		50.00	200.00	uM	Children (1-13 years old)	Both	Cystathionine beta-synthase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	6.00		4.8	7.40	uM	Adult (>18 years old)	Both	Homocystinuria	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified			2.74	7.62	uM	Children (1 - <7 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			2.89	9.99	uM	Infant (5 days - <1 year old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			3.40	8.43	uM	Children (7 - <12 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			4.069	10.36	uM	Adolescent (12 - <15 years old)	Female	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			4.73	10.43	uM	Adolescent (12 - <15 years old)	Male	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			4.96	11.91	uM	Adolescent (15 - <19 years old)	Female	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			5.47	13.39	uM	Adolescent (15 - <19 years old)	Male	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			1	18	uM	Infant (0-1 year old)	Both	Normal	HMDB	Clinical and Laboratory Barriers to the Timely Diagnosis of Sulphite Oxidase Deficiency. Proceedings of Singapore Healthcare, 19(2), 94-100.
Human Saliva	Detected and Quantified	2.92	2.27			uM	Adult (>18 years old)	Both	Normal	HMDB	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21190195
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000742

DrugBank ID

DB04422

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Homocysteine

METLIN ID

3256

PubChem Compound

91552

PDB ID

Not Available

ChEBI ID

17588

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Eskes TK: Homocysteine and human reproduction. Clin Exp Obstet Gynecol. 2000;27(3-4):157-67. [PubMed:11214939 ]
Selley ML, Close DR, Stern SE: The effect of increased concentrations of homocysteine on the concentration of (E)-4-hydroxy-2-nonenal in the plasma and cerebrospinal fluid of patients with Alzheimer's disease. Neurobiol Aging. 2002 May-Jun;23(3):383-8. doi: 10.1016/s0197-4580(01)00327-x. [PubMed:11959400 ]
Hossain GS, van Thienen JV, Werstuck GH, Zhou J, Sood SK, Dickhout JG, de Koning AB, Tang D, Wu D, Falk E, Poddar R, Jacobsen DW, Zhang K, Kaufman RJ, Austin RC: TDAG51 is induced by homocysteine, promotes detachment-mediated programmed cell death, and contributes to the cevelopment of atherosclerosis in hyperhomocysteinemia. J Biol Chem. 2003 Aug 8;278(32):30317-27. doi: 10.1074/jbc.M212897200. Epub 2003 May 8. [PubMed:12738777 ]
Muller T, Renger K, Kuhn W: Levodopa-associated increase of homocysteine levels and sural axonal neurodegeneration. Arch Neurol. 2004 May;61(5):657-60. doi: 10.1001/archneur.61.5.657. [PubMed:15148140 ]
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Terzolo M, Allasino B, Bosio S, Brusa E, Daffara F, Ventura M, Aroasio E, Sacchetto G, Reimondo G, Angeli A, Camaschella C: Hyperhomocysteinemia in patients with Cushing's syndrome. J Clin Endocrinol Metab. 2004 Aug;89(8):3745-51. doi: 10.1210/jc.2004-0079. [PubMed:15292300 ]
Krantz JS, Mack WJ, Hodis HN, Liu CR, Liu CH, Kaufman FR: Early onset of subclinical atherosclerosis in young persons with type 1 diabetes. J Pediatr. 2004 Oct;145(4):452-7. doi: 10.1016/j.jpeds.2004.06.042. [PubMed:15480366 ]
Yu CK, Lakasing L, Papageorghiou AT, Spencer K, Nicolaides KH: Uterine artery Doppler and mid-trimester maternal plasma homocysteine in subsequent pre-eclampsia. J Matern Fetal Neonatal Med. 2004 Aug;16(2):134-9. doi: 10.1080/14767050400009287. [PubMed:15512726 ]
Winkelmayer WC, Kramar R, Curhan GC, Chandraker A, Endler G, Fodinger M, Horl WH, Sunder-Plassmann G: Fasting plasma total homocysteine levels and mortality and allograft loss in kidney transplant recipients: a prospective study. J Am Soc Nephrol. 2005 Jan;16(1):255-60. doi: 10.1681/ASN.2004070576. Epub 2004 Nov 24. [PubMed:15563562 ]
Brosnan JT: Homocysteine and cardiovascular disease: interactions between nutrition, genetics and lifestyle. Can J Appl Physiol. 2004 Dec;29(6):773-80. doi: 10.1139/h04-050. [PubMed:15630149 ]
Robinson G, Narasimhan S, Weatherall M, Beasley R: Raised plasma homocysteine levels in alcoholism: increasing the risk of heart disease and dementia? N Z Med J. 2005 Jun 3;118(1216):U1490. [PubMed:15937525 ]
Gulsen M, Yesilova Z, Bagci S, Uygun A, Ozcan A, Ercin CN, Erdil A, Sanisoglu SY, Cakir E, Ates Y, Erbil MK, Karaeren N, Dagalp K: Elevated plasma homocysteine concentrations as a predictor of steatohepatitis in patients with non-alcoholic fatty liver disease. J Gastroenterol Hepatol. 2005 Sep;20(9):1448-55. doi: 10.1111/j.1440-1746.2005.03891.x. [PubMed:16105135 ]
Siroka R, Trefil L, Rajdl D, Racek J, Rusnakova H, Cibulka R, Eiselt J, Filipovsky J: Asymmetric dimethylarginine, homocysteine and renal function--is there a relation? Clin Chem Lab Med. 2005;43(10):1147-50. doi: 10.1515/CCLM.2005.199. [PubMed:16197312 ]
Giladi N, Mordechovich M, Gruendlinger L, Shabtai H, Merims D, Naor S, Baltadzhieva R, Hausdorff JM, Gur AY, Bornstein NM: "Brain Screen": A self-referral, screening program for strokes, falls and dementia risk factors. J Neurol. 2006 Mar;253(3):307-15. doi: 10.1007/s00415-005-0986-6. Epub 2005 Oct 10. [PubMed:16208527 ]
Serot JM, Barbe F, Arning E, Bottiglieri T, Franck P, Montagne P, Nicolas JP: Homocysteine and methylmalonic acid concentrations in cerebrospinal fluid: relation with age and Alzheimer's disease. J Neurol Neurosurg Psychiatry. 2005 Nov;76(11):1585-7. doi: 10.1136/jnnp.2004.056119. [PubMed:16227558 ]
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Akoglu B, Wondra K, Caspary WF, Faust D: Determinants of fasting total serum homocysteine levels in liver transplant recipients. Exp Clin Transplant. 2006 Jun;4(1):462-6. [PubMed:16827644 ]
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Showing metabocard for L-Homocysteine (MMDBc0029477)

MOL for #<Metabolite:0x000055d249396c48>

3D MOL for #<Metabolite:0x000055d249396c48>

3D SDF for #<Metabolite:0x000055d249396c48>

3D-SDF for #<Metabolite:0x000055d249396c48>

PDB for #<Metabolite:0x000055d249396c48>

3D PDB for #<Metabolite:0x000055d249396c48>

SMILES for #<Metabolite:0x000055d249396c48>

INCHI for #<Metabolite:0x000055d249396c48>

Structure for #<Metabolite:0x000055d249396c48>

3D Structure for #<Metabolite:0x000055d249396c48>