Hmdb loader
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
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:07 UTC
Update Date2022-03-07 02:52:09 UTC
HMDB IDHMDB0029389
Secondary Accession Numbers
  • HMDB29389
Metabolite Identification
Common Name(+)-threo-2-Amino-3,4-dihydroxybutanoic acid
Description(+)-threo-2-Amino-3,4-dihydroxybutanoic acid belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review very few articles have been published on (+)-threo-2-Amino-3,4-dihydroxybutanoic acid.
Structure
Data?1582753411
Synonyms
ValueSource
(+)-Threo-2-amino-3,4-dihydroxybutanoateGenerator
(+)-Threo-formHMDB
2-Amino-3,4-dihydroxybutanoic acidHMDB
Chemical FormulaC4H9NO4
Average Molecular Weight135.1186
Monoisotopic Molecular Weight135.053157781
IUPAC Name2-amino-3,4-dihydroxybutanoic acid
Traditional Name2-amino-3,4-dihydroxybutanoic acid
CAS Registry Number21768-44-5
SMILES
NC(C(O)CO)C(O)=O
InChI Identifier
InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)
InChI KeyJBNUARFQOCGDRK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Hydroxy acid
  • Fatty acid
  • 1,3-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Primary alcohol
  • Primary aliphatic amine
  • Primary amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point214 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility357 g/LALOGPS
logP-3.4ALOGPS
logP-4.5ChemAxon
logS0.42ALOGPS
pKa (Strongest Acidic)1.92ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28 m³·mol⁻¹ChemAxon
Polarizability12.01 ųChemAxon
Number of Rings0ChemAxon
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]+127.63831661259
DarkChem[M-H]-123.88731661259
DeepCCS[M+H]+123.02230932474
DeepCCS[M-H]-120.22230932474
DeepCCS[M-2H]-156.75830932474
DeepCCS[M+Na]+131.5530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-threo-2-Amino-3,4-dihydroxybutanoic acidNC(C(O)CO)C(O)=O2479.5Standard polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acidNC(C(O)CO)C(O)=O1330.9Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acidNC(C(O)CO)C(O)=O1859.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TMS,isomer #1C[Si](C)(C)OC(CO)C(N)C(=O)O1456.8Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TMS,isomer #2C[Si](C)(C)OCC(O)C(N)C(=O)O1475.7Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)C(N)C(O)CO1432.0Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TMS,isomer #4C[Si](C)(C)NC(C(=O)O)C(O)CO1500.1Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)C(N)C(=O)O1515.2Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(N)C(CO)O[Si](C)(C)C1472.2Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TMS,isomer #3C[Si](C)(C)NC(C(=O)O)C(CO)O[Si](C)(C)C1534.3Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TMS,isomer #4C[Si](C)(C)OCC(O)C(N)C(=O)O[Si](C)(C)C1497.9Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TMS,isomer #5C[Si](C)(C)NC(C(=O)O)C(O)CO[Si](C)(C)C1578.3Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TMS,isomer #6C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(O)CO1529.2Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TMS,isomer #7C[Si](C)(C)N(C(C(=O)O)C(O)CO)[Si](C)(C)C1713.3Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)C(N)C(=O)O[Si](C)(C)C1543.8Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TMS,isomer #2C[Si](C)(C)NC(C(=O)O)C(CO[Si](C)(C)C)O[Si](C)(C)C1598.0Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TMS,isomer #3C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(CO)O[Si](C)(C)C1578.6Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TMS,isomer #4C[Si](C)(C)OC(CO)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1724.1Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TMS,isomer #5C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(O)CO[Si](C)(C)C1594.1Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TMS,isomer #6C[Si](C)(C)OCC(O)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1784.2Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TMS,isomer #7C[Si](C)(C)OC(=O)C(C(O)CO)N([Si](C)(C)C)[Si](C)(C)C1688.5Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #1C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C1618.8Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #1C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C1657.2Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #2C[Si](C)(C)OCC(O[Si](C)(C)C)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1764.7Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #2C[Si](C)(C)OCC(O[Si](C)(C)C)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1700.5Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #3C[Si](C)(C)OC(=O)C(C(CO)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1737.0Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #3C[Si](C)(C)OC(=O)C(C(CO)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1688.7Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #4C[Si](C)(C)OCC(O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1764.4Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TMS,isomer #4C[Si](C)(C)OCC(O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1689.6Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,5TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1800.0Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,5TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1774.9Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CO)C(N)C(=O)O1698.4Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(O)C(N)C(=O)O1732.0Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(N)C(O)CO1661.7Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(C(=O)O)C(O)CO1757.2Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(N)C(=O)O1970.6Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)C(CO)O[Si](C)(C)C(C)(C)C1904.8Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C(=O)O)C(CO)O[Si](C)(C)C(C)(C)C1980.1Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)C(N)C(=O)O[Si](C)(C)C(C)(C)C1939.5Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(C(=O)O)C(O)CO[Si](C)(C)C(C)(C)C2044.6Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)CO1995.4Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C(C(=O)O)C(O)CO)[Si](C)(C)C(C)(C)C2107.4Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(N)C(=O)O[Si](C)(C)C(C)(C)C2160.2Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C(=O)O)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2208.1Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO)O[Si](C)(C)C(C)(C)C2198.2Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(CO)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2343.6Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)CO[Si](C)(C)C(C)(C)C2217.6Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OCC(O)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2394.5Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=O)C(C(O)CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2339.9Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2407.9Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2392.2Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2588.6Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2459.9Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C(CO)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2561.1Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C(CO)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2453.0Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2597.3Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2470.7Standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2823.3Semi standard non polar33892256
(+)-threo-2-Amino-3,4-dihydroxybutanoic acid,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2665.4Standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000470
KNApSAcK IDNot Available
Chemspider ID3137512
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3914727
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .