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Showing NP-Card for Phosphoguanidinoacetate (NP0087076)

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Record Information
Version2.0
Created at2022-05-11 16:39:20 UTC
Updated at2022-05-11 16:39:20 UTC
NP-MRD IDNP0087076
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhosphoguanidinoacetate
DescriptionPhosphoguanidinoacetate, also known as guanidinoacetate phosphate or phosphoglycocyamine, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. A guanidinoacetate having a phospho group attached to the primary amino part of the guanidine moiety. Phosphoguanidinoacetate is found in Apis cerana. Phosphoguanidinoacetate was first documented in 1991 (PMID: 1667626). Phosphoguanidinoacetate is a very strong basic compound (based on its pKa) (PMID: 9386672).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087076 (Phosphoguanidinoacetate)


  Mrv0541 02231219472D          

 12 11  0  0  0  0            999 V2000
   14.2139  -15.2218    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.8014  -14.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4994  -15.6343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0719  -17.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6264  -15.9363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6429  -17.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9284  -14.8093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3573  -14.8093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6429  -16.0468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3573  -16.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6429  -15.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3573  -17.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  5  2  0  0  0  0
  1  7  1  0  0  0  0
  4 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7 11  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0087076 (Phosphoguanidinoacetate)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.1295   -1.8516   -0.5138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -0.7691    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537   -0.0364    0.6344 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221   -0.3196    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442    0.8441    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    1.8733    0.7161 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2305    0.8158   -0.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -0.4936    0.9629 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6191    0.3928   -0.0174 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.8928   -0.4173   -1.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8911    1.8793   -0.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486    0.7304    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026   -1.7522   -1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390   -2.7876   -0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4473   -1.2113    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478   -0.5136   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3285    0.9257   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6512   -0.8246    1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054    2.1655    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5628    1.3500    0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  8  1  0
  8  9  1  0
  9 11  1  0
  9 12  1  0
  9 10  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  5  6  2  0
  1 13  1  0
  1 14  1  0
  8 18  1  0
 11 19  1  0
 12 20  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

3D SDF for NP0087076 (Phosphoguanidinoacetate)


  Mrv0541 02231219472D          

 12 11  0  0  0  0            999 V2000
   14.2139  -15.2218    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.8014  -14.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4994  -15.6343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0719  -17.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6264  -15.9363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6429  -17.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9284  -14.8093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3573  -14.8093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6429  -16.0468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3573  -16.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6429  -15.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3573  -17.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  5  2  0  0  0  0
  1  7  1  0  0  0  0
  4 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7 11  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N\C(NP(O)(O)=O)=N/CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H8N3O5P/c4-3(5-1-2(7)8)6-12(9,10)11/h1H2,(H,7,8)(H5,4,5,6,9,10,11)

> <INCHI_KEY>
UUZLOPBEONRDRY-UHFFFAOYSA-N

> <FORMULA>
C3H8N3O5P

> <MOLECULAR_WEIGHT>
197.0865

> <EXACT_MASS>
197.020156893

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
15.060495719541318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(E)-[amino(phosphonoamino)methylidene]amino]acetic acid

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-2.567900216413178

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.0485076448980846

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.0582056351810936

> <JCHEM_PKA_STRONGEST_BASIC>
10.885514647700818

> <JCHEM_POLAR_SURFACE_AREA>
145.24

> <JCHEM_REFRACTIVITY>
37.5904

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-[amino(phosphonoamino)methylidene]amino]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0087076 (Phosphoguanidinoacetate)

Download
PDB for NP0087076 (Phosphoguanidinoacetate)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      26.533 -28.414   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      25.763 -27.080   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      25.199 -29.184   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      31.868 -33.034   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.303 -29.748   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      29.200 -33.034   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      27.866 -27.644   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      30.534 -27.644   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      29.200 -29.954   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      30.534 -30.724   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.200 -28.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.534 -32.264   0.000  0.00  0.00           C+0
CONECT    1    2    3    5    7                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   12                                                            
CONECT    5    1                                                            
CONECT    6   12                                                            
CONECT    7    1   11                                                       
CONECT    8   11                                                            
CONECT    9   10   11                                                       
CONECT   10    9   12                                                       
CONECT   11    7    8    9                                                  
CONECT   12    4    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0087076 (Phosphoguanidinoacetate)
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SMILES for NP0087076 (Phosphoguanidinoacetate)
N\C(NP(O)(O)=O)=N/CC(O)=O
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INCHI for NP0087076 (Phosphoguanidinoacetate)
InChI=1S/C3H8N3O5P/c4-3(5-1-2(7)8)6-12(9,10)11/h1H2,(H,7,8)(H5,4,5,6,9,10,11)
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View in JSmol
Synonyms
ValueSource
(N'-phosphonocarbamimidamido)acetic acidChEBI
(N'-phosphonoguanidino)acetic acidChEBI
Guanidinoacetate phosphateChEBI
PhosphoguanidoacetateChEBI
(N'-phosphonocarbamimidamido)acetateGenerator
(N'-phosphonoguanidino)acetateGenerator
Guanidinoacetic acid phosphoric acidGenerator
Phosphoguanidoacetic acidGenerator
Phosphoguanidinoacetic acidGenerator
PhosphoglycocyamineHMDB
PhosphoguanidinoacetateChEBI
Chemical FormulaC3H8N3O5P
Average Mass197.0865 Da
Monoisotopic Mass197.02016 Da
IUPAC Name2-[(E)-[amino(phosphonoamino)methylidene]amino]acetic acid
Traditional Name[(E)-[amino(phosphonoamino)methylidene]amino]acetic acid
CAS Registry NumberNot Available
SMILES
N\C(NP(O)(O)=O)=N/CC(O)=O
InChI Identifier
InChI=1S/C3H8N3O5P/c4-3(5-1-2(7)8)6-12(9,10)11/h1H2,(H,7,8)(H5,4,5,6,9,10,11)
InChI KeyUUZLOPBEONRDRY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids and derivatives  
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
    • 

  • Organic phosphoric acid derivative
    • 

  • Guanidine
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Carboximidamide
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen 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-2ALOGPS
logP-2.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)-1.1ChemAxon
pKa (Strongest Basic)10.89ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.24 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.59 m³·mol⁻¹ChemAxon
Polarizability15.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003705  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023217  
KNApSAcK IDNot Available
Chemspider ID164212  
KEGG Compound IDC03166  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6976  
PubChem Compound188984  
PDB IDNot Available
ChEBI ID16034  
Good Scents IDNot Available
References
General References
  1. Shirokane Y, Nakajima M, Mizusawa K: A new enzymatic assay of urinary guanidinoacetic acid. Clin Chim Acta. 1991 Oct 31;202(3):227-36. [PubMed:1667626  ] 
  2. Schulze A, Hess T, Wevers R, Mayatepek E, Bachert P, Marescau B, Knopp MV, De Deyn PP, Bremer HJ, Rating D: Creatine deficiency syndrome caused by guanidinoacetate methyltransferase deficiency: diagnostic tools for a new inborn error of metabolism. J Pediatr. 1997 Oct;131(4):626-31. doi: 10.1016/s0022-3476(97)70075-1. [PubMed:9386672  ]