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Showing NP-Card for 2-amino-3,4-dihydroxybutanoic acid (NP0215436)

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Record Information
Version2.0
Created at2022-09-05 15:03:50 UTC
Updated at2022-09-05 15:03:50 UTC
NP-MRD IDNP0215436
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-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) (+)-threo-2-Amino-3,4-dihydroxybutanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (+)-threo-2-Amino-3,4-dihydroxybutanoic acid has been detected, but not quantified in, mushrooms. 2-amino-3,4-dihydroxybutanoic acid is found in Hypsizygus ulmarius. This could make (+)-threo-2-amino-3,4-dihydroxybutanoic acid a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)

Structure #1
  Mrv0541 02241206592D          

  9  8  0  0  0  0            999 V2000
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
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3D MOL for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.7853   -1.2501   -0.3546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.2584   -0.4017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2743    1.0388   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    1.1355    0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5484    2.2205    0.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -0.7238    0.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2122   -0.9879    1.6928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.2131    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8088    0.4396   -1.2130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0066   -1.5199    0.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247   -2.0693   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -0.1826   -1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142    2.9859   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596   -1.7009   -0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -0.2291    2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4572    1.1765    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5578   -0.2117    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -0.0762   -1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  6 14  1  6
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
  5 13  1  0
M  END
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3D SDF for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)

Structure #1
  Mrv0541 02241206592D          

  9  8  0  0  0  0            999 V2000
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215436

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
JBNUARFQOCGDRK-UHFFFAOYSA-N

> <FORMULA>
C4H9NO4

> <MOLECULAR_WEIGHT>
135.1186

> <EXACT_MASS>
135.053157781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
12.00941365585029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3,4-dihydroxybutanoic acid

> <ALOGPS_LOGP>
-3.36

> <JCHEM_LOGP>
-4.517531650626965

> <ALOGPS_LOGS>
0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.79773528247857

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9232639848113706

> <JCHEM_PKA_STRONGEST_BASIC>
8.62379843972846

> <JCHEM_POLAR_SURFACE_AREA>
103.78000000000002

> <JCHEM_REFRACTIVITY>
28.0035

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3,4-dihydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)

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PDB for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.310  -0.206   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    8    9                                                  
CONECT    5    3                                                            
CONECT    6    1                                                            
CONECT    7    2                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)
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SMILES for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)
NC(C(O)CO)C(O)=O
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INCHI for NP0215436 (2-amino-3,4-dihydroxybutanoic acid)
InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)
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View in JSmol
Synonyms
ValueSource
(+)-Threo-2-amino-3,4-dihydroxybutanoateGenerator
(+)-Threo-formHMDB
2-Amino-3,4-dihydroxybutanoic acidHMDB
Chemical FormulaC4H9NO4
Average Mass135.1186 Da
Monoisotopic Mass135.05316 Da
IUPAC Name2-amino-3,4-dihydroxybutanoic acid
Traditional Name2-amino-3,4-dihydroxybutanoic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lyophyllum ulmariumLOTUS Database
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
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-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
HMDB IDHMDB0029389  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]