Showing Compound L-Homocystine (FDB022176)

Record Information

Version

1.0

Creation date

2011-09-21 00:09:35 UTC

Update date

2015-10-09 22:30:37 UTC

Primary ID

FDB022176

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Homocystine

Description

Homocystine is the double-bonded form of homocysteine, but it occurs only transiently before being converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfide account for >98% of total homocysteine in plasma from healthy individuals. (PMID 11592966) Oxidation of low-density lipoprotein (LDL) is thought to be a major factor in the pathophysiology of atherosclerosis. Elevated plasma homocysteine is an accepted risk factor for atherosclerosis, and may act through LDL oxidation, although this is controversial. However, the major thiol in plasma is cysteine, which is present at concentrations approximately 10 times greater than homocysteine; therefore homocystine in plasma is insignificant, and consequently homocystine is unlikely to influence LDL oxidation in vivo. (PMID 14732479) Increasing evidence supports a role for an elevation of homocysteine in schizophrenia. It has been demonstrated that neural tube defects are related to a genetic defect in homocysteine metabolism. Sufficient intake of folic acid is believed to reduce this risk by enhancing methylation of homocysteine and its conversion to methionine, thereby compensating for this genetic defect. Plasma homocysteine levels are elevated when folate levels are in the lower half of the normal range. (PMID 16143442 ) [HMDB]

CAS Number

626-72-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
[S-(R,R)]-4,4'-dithiobis-2-amino-Butanoate	hmdb
[S-(R,R)]-4,4'-dithiobis-2-amino-Butanoic acid	hmdb
4,4'-dithiobis-2-amino-L-Butyrate	hmdb
4,4'-dithiobis-2-amino-L-Butyric acid	hmdb
4,4'-Dithiobis(2-aminobutyric acid)	hmdb
L-Homocystine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	4.5 g/L	ALOGPS
logP	-4.2	ALOGPS
logP	-5.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	64.38 m³·mol⁻¹	ChemAxon
Polarizability	26.92 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

Chemical Formula

C8H16N2O4S2

IUPAC name

2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

InChI Identifier

InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6?/m0/s1

InChI Key

ZTVZLYBCZNMWCF-ZBHICJROSA-N

Isomeric SMILES

NC(CCSSCC[C@H](N)C(O)=O)C(O)=O

Average Molecular Weight

268.354

Monoisotopic Molecular Weight

268.05514839

Classification

Not classified

Ontology

Physiological effect

Health effect:

Health condition:

Homocystinuria

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Homocystine, non-derivatized, GC-MS Spectrum	splash10-004i-0910000000-965ac587d29ef8ef887e	Spectrum
GC-MS	L-Homocystine, non-derivatized, GC-MS Spectrum	splash10-004i-1910000000-f9e93d28a230da8e9833	Spectrum
GC-MS	L-Homocystine, non-derivatized, GC-MS Spectrum	splash10-004i-0910000000-965ac587d29ef8ef887e	Spectrum
GC-MS	L-Homocystine, non-derivatized, GC-MS Spectrum	splash10-004i-1910000000-f9e93d28a230da8e9833	Spectrum
Predicted GC-MS	L-Homocystine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fdo-9610000000-e10491cf3224336e3f4a	Spectrum
Predicted GC-MS	L-Homocystine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9322000000-c71d91c4e21c8dc7e38b	Spectrum
Predicted GC-MS	L-Homocystine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Homocystine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-eed9e6a87dcd87f2429a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9200000000-ff66e8130cc84f2f9307	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-c290f653e9d9de756e61	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gi0-0290000000-0d5b5e0ed113894b2134	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adi-4940000000-fe801a7a155db92879a5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9600000000-fa16bd387fed9ef4ae35	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0590000000-079299cfa664ba6bb1b7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-2920000000-b1d40f0689b373431812	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01bi-9600000000-d4d8be33875dbb26d641	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1490000000-14633966e3aac1b76927	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-3900000000-5e78746bf82c4b74e2da	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9100000000-cf211c8a88522ecadb5f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02t9-3920000000-03ece081c0f32738cbb4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4900000000-612a915c1fc3a29beb9e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9100000000-f378c8e7860863830ce2	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	Spectrum

External Links

ChemSpider ID

62590

ChEMBL ID

Not Available

KEGG Compound ID

C01817

Pubchem Compound ID

69382

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00676

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound L-Homocystine (FDB022176)

Structure for FDB022176 (L-Homocystine)