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Showing NP-Card for n-hydroxyglycine (NP0246834)

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Record Information
Version1.0
Created at2022-09-07 08:25:32 UTC
Updated at2022-09-07 08:25:32 UTC
NP-MRD IDNP0246834
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-hydroxyglycine
DescriptionN-hydroxyglycine, also known as hydroxyaminoacetate, belongs to the class of organic compounds known as n-hydroxyl-alpha-amino acids. These are alpha amino acids that carry a hydroxyl group at the N-terminal. n-hydroxyglycine is found in Penicillium citrinum. It was first documented in 2005 (PMID: 16216260). Based on a literature review a small amount of articles have been published on N-hydroxyglycine (PMID: 23819828) (PMID: 27380298) (PMID: 24832734) (PMID: 20093117).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0246834 (n-hydroxyglycine)


  Mrv1652309072210252D          

  6  5  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    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
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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  0  0  0  0
M  END
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3D MOL for NP0246834 (n-hydroxyglycine)

     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
    1.0911    1.3595   -0.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900    0.5430    0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617    0.3251    0.9574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1366   -0.1359    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -0.4958   -0.5594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164    0.2495   -0.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8834   -0.4310    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910    0.4031    1.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739   -1.1499    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3647   -1.4811   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863    0.8135   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  6 11  1  0
  5 10  1  0
  4  8  1  0
  4  9  1  0
  3  7  1  0
M  END
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3D SDF for NP0246834 (n-hydroxyglycine)


  Mrv1652309072210252D          

  6  5  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    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
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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  0  0  0  0
M  END
> <DATABASE_ID>
NP0246834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ONCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H5NO3/c4-2(5)1-3-6/h3,6H,1H2,(H,4,5)

> <INCHI_KEY>
NPWGWQRXHVJJRD-UHFFFAOYSA-N

> <FORMULA>
C2H5NO3

> <MOLECULAR_WEIGHT>
91.066

> <EXACT_MASS>
91.026943025

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.56892103740118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxyamino)acetic acid

> <JCHEM_LOGP>
-1.648180293417024

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.18660793506248

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9955500732131322

> <JCHEM_PKA_STRONGEST_BASIC>
4.361129947715355

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
28.2608

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-hydroxyglycine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0246834 (n-hydroxyglycine)

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PDB for NP0246834 (n-hydroxyglycine)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       4.620  -2.667   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620  -0.000   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  N   UNK     0       1.540   0.000   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       0.000   0.000   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                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0246834 (n-hydroxyglycine)
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SMILES for NP0246834 (n-hydroxyglycine)
ONCC(O)=O
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INCHI for NP0246834 (n-hydroxyglycine)
InChI=1S/C2H5NO3/c4-2(5)1-3-6/h3,6H,1H2,(H,4,5)
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View in JSmol
Synonyms
ValueSource
Hydroxyaminoacetic acidChEBI
Hydroxylamino acetic acidChEBI
HydroxyaminoacetateGenerator
Hydroxylamino acetateGenerator
Chemical FormulaC2H5NO3
Average Mass91.0660 Da
Monoisotopic Mass91.02694 Da
IUPAC Name2-(hydroxyamino)acetic acid
Traditional NameN-hydroxyglycine
CAS Registry NumberNot Available
SMILES
ONCC(O)=O
InChI Identifier
InChI=1S/C2H5NO3/c4-2(5)1-3-6/h3,6H,1H2,(H,4,5)
InChI KeyNPWGWQRXHVJJRD-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
Penicillium citrinumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-hydroxyl-alpha-amino acids. These are alpha amino acids that carry a hydroxyl group at the N-terminal.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentN-hydroxyl-alpha-amino acids  
Alternative Parents
Substituents
  • N-hydroxyl-alpha-amino acid
    • 

  • N-organohydroxylamine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • 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-1.6ChemAxon
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)4.36ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.26 m³·mol⁻¹ChemAxon
Polarizability7.57 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 ID18005  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19070  
PDB IDNot Available
ChEBI ID38049  
Good Scents IDNot Available
References
General References
  1. Kim Y, In Y, Ishida T, Onaka H, Igarashi Y: Biosynthetic origin of alchivemycin A, a new polyketide from Streptomyces and absolute configuration of alchivemycin B. Org Lett. 2013 Jul 19;15(14):3514-7. doi: 10.1021/ol401071j. Epub 2013 Jul 2. [PubMed:23819828  ] 
  2. Arezki NR, Williams AC, Cobb AJ, Brown MB: Design, synthesis and characterization of linear unnatural amino acids for skin moisturization. Int J Cosmet Sci. 2017 Feb;39(1):72-82. doi: 10.1111/ics.12351. Epub 2016 Jul 24. [PubMed:27380298  ] 
  3. Singh D, Sharma KK, Dhar MS, Virdi JS: Molecular modeling and docking of novel laccase from multiple serotype of Yersinia enterocolitica suggests differential and multiple substrate binding. Biochem Biophys Res Commun. 2014 Jun 20;449(1):157-62. doi: 10.1016/j.bbrc.2014.05.003. Epub 2014 May 14. [PubMed:24832734  ] 
  4. Mehrotra S, Bopanna MP, Bulusu V, Balaram H: Adenine metabolism in Plasmodium falciparum. Exp Parasitol. 2010 Jun;125(2):147-51. doi: 10.1016/j.exppara.2010.01.002. Epub 2010 Jan 20. [PubMed:20093117  ] 
  5. Hattori M, Konishi H, Tamura Y, Konno K, Sogawa K: Laccase-type phenoloxidase in salivary glands and watery saliva of the green rice leafhopper, Nephotettix cincticeps. J Insect Physiol. 2005 Dec;51(12):1359-65. doi: 10.1016/j.jinsphys.2005.08.010. Epub 2005 Oct 10. [PubMed:16216260  ] 
  6. LOTUS database [Link]