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Showing metabocard for Homocysteine thiolactone (HMDB0002287)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:46 UTC
Update Date2023-02-21 17:16:19 UTC
HMDB IDHMDB0002287
Secondary Accession Numbers
  • HMDB02287
Metabolite Identification
Common NameHomocysteine thiolactone
DescriptionElevated level of the nonprotein amino acid homocysteine (Hcy) is a risk factor for cardiovascular diseases, neurodegenerative diseases, and neural tube defects. Metabolic conversion of Hcy to a chemically reactive metabolite, Hcy-thiolactone, catalyzed by methionyl-tRNA synthetase is the first step in a pathway that contributes to Hcy toxicity in humans. (PMID 16702349 ). The only known source of Hcy in the human body is dietary protein methionine; subsequent examinations of individual dietary amino acids have led to the conclusion that methionine, ingested in excess, is the most toxic amino acid. (Harper AE, Benevenga NJ, Wohlheuter RM. Effects of ingestion of disproportionate amounts of amino acids. Physiol Rev. 1970;50: 428 - 58; Benevenga NJ, Steele RD. Adverse effects of excessive consumption of amino acids. Annu Rev Nutr. 1984; 4:157-81). Animals fed high-protein or high-methionine diets for 2 years developed hyperhomocysteinemia and evidence of vascular disease (Fau D, Preret J, Hadjiisky P. Effects of ingestion of high protein or excess methionine diets by rats for two years. J Nutr. 1988; 118:128-33).
Structure
Data?1676999779
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002287 (Homocysteine thiolactone)


  Mrv0541 02231219282D          

  7  7  0  0  0  0            999 V2000
   10.9622   -6.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6302   -6.1044    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2165   -7.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2972   -6.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0416   -7.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2879   -6.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7848   -7.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  1  2  0  0  0  0
  7  3  1  0  0  0  0
M  END
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3D MOL for HMDB0002287 (Homocysteine thiolactone)

HMDB0002287
     RDKit          3D
Homocysteine thiolactone
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9565   -0.1402   -0.1446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5914    0.1829   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687   -0.7862    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7477   -0.3304   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    1.4628    0.1799 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2174    1.4709    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295    2.3178    0.6654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    0.4187    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -1.1307   -0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116    0.2173   -1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -0.5925    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -1.8173   -0.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543   -0.7794    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -0.4937   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
M  END
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3D SDF for HMDB0002287 (Homocysteine thiolactone)


  Mrv0541 02231219282D          

  7  7  0  0  0  0            999 V2000
   10.9622   -6.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6302   -6.1044    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2165   -7.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2972   -6.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0416   -7.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2879   -6.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7848   -7.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  1  2  0  0  0  0
  7  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002287

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1CCSC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2

> <INCHI_KEY>
KIWQWJKWBHZMDT-UHFFFAOYSA-N

> <FORMULA>
C4H7NOS

> <MOLECULAR_WEIGHT>
117.169

> <EXACT_MASS>
117.024834541

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.432562330235712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-aminothiolan-2-one

> <ALOGPS_LOGP>
-0.51

> <JCHEM_LOGP>
-0.250338875

> <ALOGPS_LOGS>
-0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.8258042417703395

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
29.7591

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DL-homocysteine thiolactone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002287 (Homocysteine thiolactone)

HMDB0002287
     RDKit          3D
Homocysteine thiolactone
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9565   -0.1402   -0.1446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5914    0.1829   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687   -0.7862    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7477   -0.3304   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    1.4628    0.1799 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2174    1.4709    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295    2.3178    0.6654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    0.4187    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -1.1307   -0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116    0.2173   -1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -0.5925    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -1.8173   -0.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543   -0.7794    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -0.4937   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
M  END
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PDB for HMDB0002287 (Homocysteine thiolactone)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.463 -12.299   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      21.710 -11.395   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      20.937 -13.764   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.955 -12.301   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.478 -13.765   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      19.204 -11.949   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      20.132 -14.844   0.000  0.00  0.00           N+0
CONECT    1    2    3    6                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    7                                                  
CONECT    4    2    5                                                       
CONECT    5    3    4                                                       
CONECT    6    1                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0002287 (Homocysteine thiolactone)

COMPND    HMDB0002287
HETATM    1  N1  UNL     1      -1.957  -0.140  -0.145  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.591   0.183  -0.361  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.369  -0.786   0.288  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.748  -0.330  -0.216  1.00  0.00           C  
HETATM    5  S1  UNL     1       1.562   1.463   0.180  1.00  0.00           S  
HETATM    6  C4  UNL     1      -0.217   1.471   0.240  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.930   2.318   0.665  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.455   0.419   0.554  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.206  -1.131  -0.211  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.312   0.217  -1.453  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.369  -0.592   1.365  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.237  -1.817  -0.011  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.554  -0.779   0.392  1.00  0.00           H  
HETATM   14  H7  UNL     1       1.830  -0.494  -1.287  1.00  0.00           H  
CONECT    1    2    8    9
CONECT    2    3    6   10
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5    6
CONECT    6    7    7
END
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SMILES for HMDB0002287 (Homocysteine thiolactone)

NC1CCSC1=O
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INCHI for HMDB0002287 (Homocysteine thiolactone)

InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
( -)-3-amino-2-ThiolanonHMDB
( -)-3-aminotetrahydro-2-ThiophenonHMDB
(+-)-3-aminodihydro-2(3H)-ThiophenoneHMDB
3-aminodihydro-2(3H)-ThiophenoneHMDB
DL-3-aminotetrahydro-2-ThiophenoneHMDB
DL-Homocysteine thiolactoneHMDB
L-Homocysteine thiolactoneHMDB
Chemical FormulaC4H7NOS
Average Molecular Weight117.169
Monoisotopic Molecular Weight117.024834541
IUPAC Name3-aminothiolan-2-one
Traditional NameDL-homocysteine thiolactone
CAS Registry Number3622-59-1
SMILES
NC1CCSC1=O
InChI Identifier
InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2
InChI KeyKIWQWJKWBHZMDT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Thiolane
  • Carbothioic s-lactone
  • Thiocarboxylic acid ester
  • Thiolactone
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility59.3 g/LALOGPS
logP-0.51ALOGPS
logP-0.25ChemAxon
logS-0.3ALOGPS
pKa (Strongest Basic)7.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.76 m³·mol⁻¹ChemAxon
Polarizability11.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.36331661259
DarkChem[M-H]-115.99931661259
DeepCCS[M+H]+128.25130932474
DeepCCS[M-H]-126.13530932474
DeepCCS[M-2H]-162.00330932474
DeepCCS[M+Na]+136.45930932474
AllCCS[M+H]+123.732859911
AllCCS[M+H-H2O]+118.932859911
AllCCS[M+NH4]+128.232859911
AllCCS[M+Na]+129.532859911
AllCCS[M-H]-124.232859911
AllCCS[M+Na-2H]-127.432859911
AllCCS[M+HCOO]-130.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.46 minutes32390414
Predicted by Siyang on May 30, 20228.215 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.96 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid278.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid571.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid312.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid76.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid212.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid60.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid249.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid260.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)690.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid559.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid40.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid625.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid197.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid216.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate610.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA422.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water261.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Homocysteine thiolactoneNC1CCSC1=O2073.8Standard polar33892256
Homocysteine thiolactoneNC1CCSC1=O1061.0Standard non polar33892256
Homocysteine thiolactoneNC1CCSC1=O1189.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Homocysteine thiolactone,1TMS,isomer #1C[Si](C)(C)NC1CCSC1=O1361.2Semi standard non polar33892256
Homocysteine thiolactone,1TMS,isomer #1C[Si](C)(C)NC1CCSC1=O1313.5Standard non polar33892256
Homocysteine thiolactone,1TMS,isomer #1C[Si](C)(C)NC1CCSC1=O2227.4Standard polar33892256
Homocysteine thiolactone,2TMS,isomer #1C[Si](C)(C)N(C1CCSC1=O)[Si](C)(C)C1561.6Semi standard non polar33892256
Homocysteine thiolactone,2TMS,isomer #1C[Si](C)(C)N(C1CCSC1=O)[Si](C)(C)C1554.8Standard non polar33892256
Homocysteine thiolactone,2TMS,isomer #1C[Si](C)(C)N(C1CCSC1=O)[Si](C)(C)C2013.1Standard polar33892256
Homocysteine thiolactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1CCSC1=O1621.9Semi standard non polar33892256
Homocysteine thiolactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1CCSC1=O1568.6Standard non polar33892256
Homocysteine thiolactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1CCSC1=O2314.5Standard polar33892256
Homocysteine thiolactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1CCSC1=O)[Si](C)(C)C(C)(C)C1979.3Semi standard non polar33892256
Homocysteine thiolactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1CCSC1=O)[Si](C)(C)C(C)(C)C2030.3Standard non polar33892256
Homocysteine thiolactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1CCSC1=O)[Si](C)(C)C(C)(C)C2037.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Homocysteine thiolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9000000000-7b8e6410972444b84efc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocysteine thiolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocysteine thiolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 10V, Positive-QTOFsplash10-014i-0900000000-8f683c9002bf43fef10d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 20V, Positive-QTOFsplash10-0076-9000000000-e26ebbd2d16a1aed58012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 40V, Positive-QTOFsplash10-0006-9100000000-649e7b0f78d61a745b452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 10V, Negative-QTOFsplash10-014i-2900000000-806166a012352ec0be632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 20V, Negative-QTOFsplash10-0aba-9000000000-a8839b6dcc9998e5eadc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 40V, Negative-QTOFsplash10-0080-9000000000-97c8bd4bc30856bdda2e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 10V, Negative-QTOFsplash10-014i-3900000000-a86fe79188b92a0f513e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 20V, Negative-QTOFsplash10-053r-9100000000-bed3e8f03e106eedf1a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 40V, Negative-QTOFsplash10-001i-9000000000-cfcd40acf2ab07b3f5f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 10V, Positive-QTOFsplash10-014l-6900000000-587ed663ed27e0d79f572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 20V, Positive-QTOFsplash10-0a4i-9600000000-974a58cb3346970c79ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocysteine thiolactone 40V, Positive-QTOFsplash10-052o-9000000000-4073e682ce58bd088e4e2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00282 +/- 0.00613 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022949
KNApSAcK IDNot Available
Chemspider ID96881
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6594
PubChem Compound107712
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTakehara, Jun; Ichikawa, Shuji; Iwane, Hiroshi. Preparation of DL-homocysteine thiolactone inorganic acid salts. Jpn. Kokai Tokkyo Koho (1998), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jakubowski H: Pathophysiological consequences of homocysteine excess. J Nutr. 2006 Jun;136(6 Suppl):1741S-1749S. [PubMed:16702349 ]
  2. Ricci G, Santoro L, Achilli M, Matarese RM, Nardini M, Cavallini D: Similarity of the oxidation products of L-cystathionine by L-amino acid oxidase to those excreted by cystathioninuric patients. J Biol Chem. 1983 Sep 10;258(17):10511-7. [PubMed:6885789 ]
  3. Jakubowski H: Homocysteine thiolactone: metabolic origin and protein homocysteinylation in humans. J Nutr. 2000 Feb;130(2S Suppl):377S-381S. [PubMed:10721911 ]
  4. Jakubowski H: Protein homocysteinylation: possible mechanism underlying pathological consequences of elevated homocysteine levels. FASEB J. 1999 Dec;13(15):2277-83. [PubMed:10593875 ]
  5. Kerkeni M, Addad F, Chauffert M, Chuniaud L, Miled A, Trivin F, Maaroufi K: Hyperhomocysteinemia, paraoxonase activity and risk of coronary artery disease. Clin Biochem. 2006 Aug;39(8):821-5. Epub 2006 Jun 7. [PubMed:16875684 ]
  6. Chwatko G, Jakubowski H: The determination of homocysteine-thiolactone in human plasma. Anal Biochem. 2005 Feb 15;337(2):271-7. [PubMed:15691507 ]