You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2020-06-04 20:29:23 UTC
Update Date2020-06-04 21:06:43 UTC
HMDB IDHMDB0240656
Secondary Accession NumbersNone
Metabolite Identification
Common NameLanthionine
DescriptionLanthionine belongs to the class of organic compounds known as L-cysteine-S-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated. Lanthionine is a uremic toxin (PMID: 30087103 ).
Structure
Data?1591304803
Synonyms
ValueSource
(R)-S-(2-Amino-2-carboxyethyl)-L-cysteineChEBI
(R,R)-2,6-Diamino-4-thiaheptanedioic acidChEBI
(R,R)-3,3'-Thiobis-(2-aminopropanoic acid)ChEBI
(R,R)-Bis(2-amino-2-carboxyethyl)sulfideChEBI
3,3'-Thiobis-L-alanineChEBI
(R,R)-2,6-Diamino-4-thiaheptanedioateGenerator
(R,R)-3,3'-Thiobis-(2-aminopropanoate)Generator
(R,R)-Bis(2-amino-2-carboxyethyl)sulphideGenerator
3,3'-ThiodialanineMeSH
LanthionineMeSH
Lanthionine, (L)-(R)-isomerMeSH
L-LanthionineHMDB
S-[(2R)-2-Amino-2-carboxyethyl]-L-cysteineHMDB
Chemical FormulaC6H12N2O4S
Average Molecular Weight208.23
Monoisotopic Molecular Weight208.051778048
IUPAC Name(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}propanoic acid
Traditional Namelanthionine
CAS Registry Number922-55-4
SMILES
N[C@@H](CSC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
InChI KeyDWPCPZJAHOETAG-IMJSIDKUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Indirect biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-4.1ALOGPS
logP-6ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.86 m³·mol⁻¹ChemAxon
Polarizability19.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID88959
KEGG Compound IDNot Available
BioCyc IDCPD-3736
BiGG IDNot Available
Wikipedia LinkLanthionine
METLIN IDNot Available
PubChem Compound98504
PDB IDNot Available
ChEBI ID21347
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mair RD, Sirich TL, Plummer NS, Meyer TW: Characteristics of Colon-Derived Uremic Solutes. Clin J Am Soc Nephrol. 2018 Sep 7;13(9):1398-1404. doi: 10.2215/CJN.03150318. Epub 2018 Aug 7. [PubMed:30087103 ]