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Showing NP-Card for (2s)-2-(hydroxyamino)butanedioic acid (NP0325637)

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Record Information
Version2.0
Created at2022-09-12 06:32:08 UTC
Updated at2022-09-12 06:32:08 UTC
NP-MRD IDNP0325637
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-(hydroxyamino)butanedioic acid
DescriptionHydroxyaspartic acid, also known as hydroxyaspartate, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-(hydroxyamino)butanedioic acid is found in Medicago sativa. (2s)-2-(hydroxyamino)butanedioic acid was first documented in 2019 (PMID: 31527229). Based on a literature review a small amount of articles have been published on Hydroxyaspartic acid (PMID: 32378891) (PMID: 35963916) (PMID: 32725837) (PMID: 32266214).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)


  Mrv1652309122208322D          

 10  9  0  0  1  0            999 V2000
    0.5230    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 O   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  2  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
    2.6664   -2.3645    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
    2.6664    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
    0.9308    0.2816   -1.8854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    0.0360   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -0.3087   -0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    0.0938    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272    0.3470    0.4267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1038    0.4260    1.7881 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830    1.3566    2.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669   -0.7718   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124   -1.4403    0.4455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -1.0861   -1.5677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -1.2799   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3106    0.8885    1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0354   -0.8470    1.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8633    1.2853   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4919   -0.4045    2.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4949    2.2148    2.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059   -0.7913   -2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5  8  1  0
  8 10  1  0
  8  9  2  0
  7 16  1  0
  6 15  1  0
  5 14  1  6
  4 12  1  0
  4 13  1  0
  3 11  1  0
 10 17  1  0
M  END
Download

3D SDF for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)


  Mrv1652309122208322D          

 10  9  0  0  1  0            999 V2000
    0.5230    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 O   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  2  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
    2.6664   -2.3645    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
    2.6664    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325637

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ON[C@@H](CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO5/c6-3(7)1-2(5-10)4(8)9/h2,5,10H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1

> <INCHI_KEY>
YDBVAWZTOAZPTJ-REOHCLBHSA-N

> <FORMULA>
C4H7NO5

> <MOLECULAR_WEIGHT>
149.102

> <EXACT_MASS>
149.032422329

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.247196556290803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(hydroxyamino)butanedioic acid

> <JCHEM_LOGP>
-1.4812274645169672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.249263280078768

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6830755526193784

> <JCHEM_PKA_STRONGEST_BASIC>
1.862671232364344

> <JCHEM_POLAR_SURFACE_AREA>
106.86

> <JCHEM_REFRACTIVITY>
38.7901

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(hydroxyamino)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)

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PDB for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       0.976   0.976   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.644   0.976   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.644  -3.644   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       4.977  -4.414   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       4.977   0.206   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.311  -2.104   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)
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SMILES for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)
ON[C@@H](CC(O)=O)C(O)=O
Download
INCHI for NP0325637 ((2s)-2-(hydroxyamino)butanedioic acid)
InChI=1S/C4H7NO5/c6-3(7)1-2(5-10)4(8)9/h2,5,10H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
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Synonyms
ValueSource
HydroxyaspartateGenerator
Chemical FormulaC4H7NO5
Average Mass149.1020 Da
Monoisotopic Mass149.03242 Da
IUPAC Name(2S)-2-(hydroxyamino)butanedioic acid
Traditional Name(2S)-2-(hydroxyamino)butanedioic acid
CAS Registry NumberNot Available
SMILES
ON[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H7NO5/c6-3(7)1-2(5-10)4(8)9/h2,5,10H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI KeyYDBVAWZTOAZPTJ-REOHCLBHSA-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
Medicago sativaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAspartic acid and derivatives  
Alternative Parents
Substituents
  • Aspartic acid or derivatives
    • 

  • N-hydroxyl-alpha-amino acid
    • 

  • Fatty acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • N-organohydroxylamine
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • 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-1.5ChemAxon
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)1.86ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.79 m³·mol⁻¹ChemAxon
Polarizability12.25 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 IDC00018064  
Chemspider ID2298353  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3033744  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Matsui K, Kan Y, Kikuchi J, Matsushima K, Takemura M, Maki H, Kozono I, Ueda T, Minagawa K: Stalobacin: Discovery of Novel Lipopeptide Antibiotics with Potent Antibacterial Activity against Multidrug-Resistant Bacteria. J Med Chem. 2020 Jun 11;63(11):6090-6095. doi: 10.1021/acs.jmedchem.0c00295. Epub 2020 May 19. [PubMed:32378891  ] 
  2. Lee Y, Seo Y, Lee B, Kwon H, Chung K, Kim YG: Divergent synthesis of biologically active L-threo-beta-hydroxyaspartates from common trans-oxazolidine dicarboxylate. Amino Acids. 2022 Aug 13. pii: 10.1007/s00726-022-03196-8. doi: 10.1007/s00726-022-03196-8. [PubMed:35963916  ] 
  3. Sun Z, Shang Z, Forelli N, Po KHL, Chen S, Brady SF, Li X: Total Synthesis of Malacidin A by beta-Hydroxyaspartic Acid Ligation-Mediated Cyclization and Absolute Structure Establishment. Angew Chem Int Ed Engl. 2020 Nov 2;59(45):19868-19872. doi: 10.1002/anie.202009092. Epub 2020 Aug 31. [PubMed:32725837  ] 
  4. Li Y, Liu L, Zhang G, He N, Guo W, Hong B, Xie Y: Potashchelins, a Suite of Lipid Siderophores Bearing Both L-threo and L-erythro Beta-Hydroxyaspartic Acids, Acquired From the Potash-Salt-Ore-Derived Extremophile Halomonas sp. MG34. Front Chem. 2020 Mar 20;8:197. doi: 10.3389/fchem.2020.00197. eCollection 2020. [PubMed:32266214  ] 
  5. Reitz ZL, Hardy CD, Suk J, Bouvet J, Butler A: Genomic analysis of siderophore beta-hydroxylases reveals divergent stereocontrol and expands the condensation domain family. Proc Natl Acad Sci U S A. 2019 Oct 1;116(40):19805-19814. doi: 10.1073/pnas.1903161116. Epub 2019 Sep 16. [PubMed:31527229  ] 
  6. LOTUS database [Link]