(4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid (CHEM045040)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 12:47:06 UTC
Update Date2016-11-09 01:23:16 UTC
Accession NumberCHEM045040
Identification
Common Name(4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
ClassSmall Molecule
DescriptionA carboxamidine heterocycle which is obtained by formal condensation of 4-amino-L-allothreonine with acetic acid.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4S,5S)-2-Methyl-4-carboxy-5-hydroxy-3,4,5,6-tetrahydropyrimidineChEBI
(4S,5S)-5-HYDROXY-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylIC ACIDChEBI
(S,S)-2-Methyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine-4-carboxylic acidChEBI
beta-HydroxyectoineChEBI
HydroxyectoineChEBI
(4S,5S)-5-HYDROXY-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylateGenerator
(S,S)-2-Methyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine-4-carboxylateGenerator
b-HydroxyectoineGenerator
Β-hydroxyectoineGenerator
5-HydroxyectoineMeSH
Chemical FormulaC6H10N2O3
Average Molecular Mass158.155 g/mol
Monoisotopic Mass158.069 g/mol
CAS Registry Number165542-15-4
IUPAC Name(4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Traditional Name5-hydroxyectoine
SMILES[H][C@]1(O)CN=C(C)N[C@]1([H])C(O)=O
InChI IdentifierInChI=1S/C6H10N2O3/c1-3-7-2-4(9)5(8-3)6(10)11/h4-5,9H,2H2,1H3,(H,7,8)(H,10,11)/t4-,5-/m0/s1
InChI KeyKIIBBJKLKFTNQO-WHFBIAKZSA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Hydropyrimidine carboxylic acid derivative
  • Beta-hydroxy acid
  • Hydropyrimidine
  • 1,4,5,6-tetrahydropyrimidine
  • Hydroxy acid
  • Imidolactam
  • Secondary alcohol
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.7 g/LALOGPS
logP-1.1ALOGPS
logP-3.2ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)2.61ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.14 m³·mol⁻¹ChemAxon
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0900000000-abd891a4570682f765b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-1900000000-abe7f8ff0e73a01a76e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-961e39aabd5018ec55f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1900000000-d5dd239ec5b802cb7432Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-5900000000-ae9f9da2de49174e2112Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ukc-9000000000-7f02ba344ab67a14b5d7Spectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID49432
PubChem Compound ID12011795
Kegg Compound IDC16432
YMDB IDNot Available
ECMDB IDM2MDB004879
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16098972