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Showing NP-Card for (2r,3s)-2-amino-3,4-dihydroxybutanoic acid (NP0228972)

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Record Information
Version2.0
Created at2022-09-06 08:50:38 UTC
Updated at2022-09-06 08:50:39 UTC
NP-MRD IDNP0228972
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3s)-2-amino-3,4-dihydroxybutanoic acid
Description21768-44-5 Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. (2r,3s)-2-amino-3,4-dihydroxybutanoic acid is found in Hypsizygus ulmarius. Based on a literature review very few articles have been published on 21768-44-5.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0228972 ((2r,3s)-2-amino-3,4-dihydroxybutanoic acid)


  Mrv1652309062210502D          

  9  8  0  0  1  0            999 V2000
    1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   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
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   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
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for NP0228972 ((2r,3s)-2-amino-3,4-dihydroxybutanoic acid)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -0.8129    1.9601    0.3634 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806    0.5314    0.6292 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6070   -0.2254   -0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981    0.3202   -0.8257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370   -1.6110   -0.0470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8217    0.2401    0.1594 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9088    0.5227   -1.1956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2878   -1.1434    0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229   -1.2459    0.1106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8080    2.0306   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7738    2.2300    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.3906    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -2.1446    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910    0.9523    0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1301    1.4794   -1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640   -1.2488    1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732   -1.9449    0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793   -1.0934   -0.8805 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  1
  6 14  1  1
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
  5 13  1  0
M  END
Download

3D SDF for NP0228972 ((2r,3s)-2-amino-3,4-dihydroxybutanoic acid)


  Mrv1652309062210502D          

  9  8  0  0  1  0            999 V2000
    1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   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
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   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
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H]([C@H](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)/t2-,3-/m1/s1

> <INCHI_KEY>
JBNUARFQOCGDRK-PWNYCUMCSA-N

> <FORMULA>
C4H9NO4

> <MOLECULAR_WEIGHT>
135.119

> <EXACT_MASS>
135.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.109541711244875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-2-amino-3,4-dihydroxybutanoic acid

> <JCHEM_LOGP>
-4.517531650626965

> <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>
28.003499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-2-amino-3,4-dihydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0228972 ((2r,3s)-2-amino-3,4-dihydroxybutanoic acid)

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PDB for NP0228972 ((2r,3s)-2-amino-3,4-dihydroxybutanoic acid)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  N   UNK     0       2.310  -0.206   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0228972 ((2r,3s)-2-amino-3,4-dihydroxybutanoic acid)
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SMILES for NP0228972 ((2r,3s)-2-amino-3,4-dihydroxybutanoic acid)
N[C@H]([C@H](O)CO)C(O)=O
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INCHI for NP0228972 ((2r,3s)-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)/t2-,3-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC4H9NO4
Average Mass135.1190 Da
Monoisotopic Mass135.05316 Da
IUPAC Name(2R,3S)-2-amino-3,4-dihydroxybutanoic acid
Traditional Name(2R,3S)-2-amino-3,4-dihydroxybutanoic acid
CAS Registry NumberNot Available
SMILES
N[C@H]([C@H](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)/t2-,3-/m1/s1
InChI KeyJBNUARFQOCGDRK-PWNYCUMCSA-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 d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentD-alpha-amino acids  
Alternative Parents
Substituents
  • D-alpha-amino acid
    • 

  • Beta-hydroxy acid
    • 

  • Short-chain hydroxy acid
    • 

  • Fatty acid
    • 

  • Hydroxy acid
    • 

  • 1,3-aminoalcohol
    • 

  • 1,2-diol
    • 

  • Amino acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary alcohol
    • 

  • Primary aliphatic amine
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Amine
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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-4.5ChemAxon
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
Polarizability12.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7991012  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9815262  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]