Np mrd loader

Record Information
Version1.0
Created at2020-11-23 19:38:41 UTC
Updated at2021-08-19 23:59:17 UTC
NP-MRD IDNP0002718
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Cysteic acid
Provided ByBMRBBMRB logo
Description(R)-cysteate, also known as L-cysteic acid or 3-sulfoalanine, 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 (R)-cysteate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. L-Cysteic acid is found in Apis cerana, Claviceps purpurea, Pseudotsuga menziesii and Puccinia graminis. It was first documented in 1996 (PMID: 8981569). Based on a literature review a significant number of articles have been published on (R)-cysteate (PMID: 17984079) (PMID: 11750815) (PMID: 21719707) (PMID: 34364050) (PMID: 34269883) (PMID: 34268896).
Structure
Thumb
Synonyms
ValueSource
(2R)-2-Amino-3-sulfopropanoic acidChEBI
2-Amino-3-sulfopropionic acidChEBI
3-SulfO-L-alanineChEBI
3-SulfoalanineChEBI
CYSTEINEsulfonIC ACIDChEBI
L-CysteateChEBI
L-Cysteic acidKegg
(2R)-2-Amino-3-sulfopropanoateGenerator
(2R)-2-Amino-3-sulphopropanoateGenerator
(2R)-2-Amino-3-sulphopropanoic acidGenerator
2-Amino-3-sulfopropionateGenerator
2-Amino-3-sulphopropionateGenerator
2-Amino-3-sulphopropionic acidGenerator
3-SulphO-L-alanineGenerator
3-SulphoalanineGenerator
CYSTEINEsulfonateGenerator
CYSTEINEsulphonateGenerator
CYSTEINEsulphonic acidGenerator
(R)-Cysteic acidGenerator
L-3-SulfoalanineHMDB
Cysteic acidHMDB
2-Amino-3-sulfopropanoic acidHMDB
CysteateHMDB
DL-Cysteic acidHMDB
Chemical FormulaC3H7NO5S
Average Mass169.1560 Da
Monoisotopic Mass169.00449 Da
IUPAC Name(2R)-2-amino-3-sulfopropanoic acid
Traditional Namecysteinesulfonic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](CS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1
InChI KeyXVOYSCVBGLVSOL-REOHCLBHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Claviceps purpureaLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pseudotsuga menziesiiLOTUS Database
Puccinia graminisLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-3ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)8.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.44 m³·mol⁻¹ChemAxon
Polarizability13.48 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0303991
DrugBank IDDB03661
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030145
KNApSAcK IDNot Available
Chemspider ID65718
KEGG Compound IDC00506
BioCyc IDL-CYSTEATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72886
PDB IDNot Available
ChEBI ID17285
Good Scents IDrw1724871
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Eichhorn E, Leisinger T: Escherichia coli utilizes methanesulfonate and L-cysteate as sole sulfur sources for growth. FEMS Microbiol Lett. 2001 Dec 18;205(2):271-5. doi: 10.1111/j.1574-6968.2001.tb10960.x. [PubMed:11750815 ]
  3. Sasahara A, Nanatani K, Enomoto M, Kuwahara S, Abe K: Substrate specificity of the aspartate:alanine antiporter (AspT) of Tetragenococcus halophilus in reconstituted liposomes. J Biol Chem. 2011 Aug 19;286(33):29044-29052. doi: 10.1074/jbc.M111.260224. Epub 2011 Jun 30. [PubMed:21719707 ]
  4. Thompson GA, Kilpatrick IC: The neurotransmitter candidature of sulphur-containing excitatory amino acids in the mammalian central nervous system. Pharmacol Ther. 1996;72(1):25-36. doi: 10.1016/s0163-7258(96)00097-6. [PubMed:8981569 ]
  5. Gorican T, Ciber L, Petek N, Svete J, Novinec M: Synthesis and kinetic characterization of hyperbolic inhibitors of human cathepsins K and S based on a succinimide scaffold. Bioorg Chem. 2021 Jul 28;115:105213. doi: 10.1016/j.bioorg.2021.105213. [PubMed:34364050 ]
  6. Schwenk ES, Pradhan B, Nalamasu R, Stolle L, Wainer IW, Cirullo M, Olsen A, Pergolizzi JV, Torjman MC, Viscusi ER: Ketamine in the Past, Present, and Future: Mechanisms, Metabolites, and Toxicity. Curr Pain Headache Rep. 2021 Jul 16;25(9):57. doi: 10.1007/s11916-021-00977-w. [PubMed:34269883 ]
  7. Han ZZ, Dong T, Ming XX, Kuang F, Zhang CP: Synthesis and Biological Evaluation of CF3 Se-Substituted alpha-Amino Acid Derivatives. ChemMedChem. 2021 Jul 15. doi: 10.1002/cmdc.202100451. [PubMed:34268896 ]