Showing NP-Card for Allantoic acid (NP0000840)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:31 UTC
NP-MRD IDNP0000840
Secondary Accession NumbersNone
Natural Product Identification
Common NameAllantoic acid
DescriptionAllantoic acid is the end product of Allantoicase [EC:3.5.3.4], An enzyme involved in uric acid degradation (Purine metabolism). Although it is commonly accepted that allantoicase is lost in mammals, it has been identified in mice and humans. (PMID 11852104 ). A crystalline, transparent, colorless substance found in the allantoic liquid of the fetal calf. It was formerly called allantoic acid and amniotic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000840 (Allantoic acid)

  Mrv1652309042000192D          

 12 11  0  0  0  0            999 V2000
    0.0000   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    0.9627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126    0.9627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1414   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.5496    0.0000 O   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  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
M  END
Download

3D MOL for NP0000840 (Allantoic acid)

HMDB0001209
     RDKit          3D
Allantoic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    3.5158    0.6337    0.8336 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2919   -0.0431    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326   -1.1550    1.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2593    0.4589   -0.2406 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597   -0.2753   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    0.4136   -0.0246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458   -0.0580    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833    0.6907    1.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525   -1.1515    1.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.6597   -1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076   -0.3374   -2.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2497   -1.3767   -2.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9429    1.2261    0.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    0.5726    1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913    1.3727   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053   -1.2246    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3192    1.3443   -0.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853    0.8640    2.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.0948    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -2.3903   -2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0000840 (Allantoic acid)

  Mrv1652309042000192D          

 12 11  0  0  0  0            999 V2000
    0.0000   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    0.9627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126    0.9627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1414   -0.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.5496    0.0000 O   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  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)NC(NC(N)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)

> <INCHI_KEY>
NUCLJNSWZCHRKL-UHFFFAOYSA-N

> <FORMULA>
C4H8N4O4

> <MOLECULAR_WEIGHT>
176.1307

> <EXACT_MASS>
176.054554764

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.589637369325168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-bis(carbamoylamino)acetic acid

> <ALOGPS_LOGP>
-2.12

> <JCHEM_LOGP>
-2.572494902

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.932920209741354

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2398093493303493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.113917117608129

> <JCHEM_POLAR_SURFACE_AREA>
147.54

> <JCHEM_REFRACTIVITY>
35.100300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
allantoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000840 (Allantoic acid)

HMDB0001209
     RDKit          3D
Allantoic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
    3.5158    0.6337    0.8336 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2919   -0.0431    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326   -1.1550    1.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2593    0.4589   -0.2406 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597   -0.2753   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    0.4136   -0.0246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458   -0.0580    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833    0.6907    1.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525   -1.1515    1.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.6597   -1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076   -0.3374   -2.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2497   -1.3767   -2.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9429    1.2261    0.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    0.5726    1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913    1.3727   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053   -1.2246    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3192    1.3443   -0.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853    0.8640    2.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.0948    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -2.3903   -2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
 12 20  1  0
M  END
Download

PDB for NP0000840 (Allantoic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000  -0.517   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.330  -1.281   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       1.330  -1.281   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.000   1.026   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -0.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.517   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.330   1.797   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.330   1.797   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -3.997  -1.281   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -2.667   1.026   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       3.997  -1.281   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.667   1.026   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9   10                                                  
CONECT    6    3   11   12                                                  
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0000840 (Allantoic acid)

COMPND    HMDB0001209
HETATM    1  N1  UNL     1       3.516   0.634   0.834  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.292  -0.043   0.586  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.133  -1.155   1.143  1.00  0.00           O  
HETATM    4  N2  UNL     1       1.259   0.459  -0.241  1.00  0.00           N  
HETATM    5  C2  UNL     1       0.060  -0.275  -0.443  1.00  0.00           C  
HETATM    6  N3  UNL     1      -1.133   0.414  -0.025  1.00  0.00           N  
HETATM    7  C3  UNL     1      -2.046  -0.058   0.929  1.00  0.00           C  
HETATM    8  N4  UNL     1      -3.183   0.691   1.269  1.00  0.00           N  
HETATM    9  O2  UNL     1      -1.852  -1.151   1.484  1.00  0.00           O  
HETATM   10  C4  UNL     1      -0.135  -0.660  -1.877  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.708  -0.337  -2.757  1.00  0.00           O  
HETATM   12  O4  UNL     1      -1.250  -1.377  -2.249  1.00  0.00           O  
HETATM   13  H1  UNL     1       3.943   1.226   0.094  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.030   0.573   1.739  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.391   1.373  -0.698  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.105  -1.225   0.127  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.319   1.344  -0.482  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.485   0.864   2.255  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.757   1.095   0.503  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.276  -2.390  -2.192  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6   10   16
CONECT    6    7   17
CONECT    7    8    9    9
CONECT    8   18   19
CONECT   10   11   11   12
CONECT   12   20
END
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SMILES for NP0000840 (Allantoic acid)

NC(=O)NC(NC(N)=O)C(O)=O
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INCHI for NP0000840 (Allantoic acid)

InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)
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View in JSmol
Synonyms
ValueSource
Bis[(aminocarbonyl)amino]acetic acidChEBI
Diureidoacetic acidChEBI
Bis[(aminocarbonyl)amino]acetateGenerator
DiureidoacetateGenerator
AllantoateGenerator
Allantoic acid, monosodium saltHMDB
Chemical FormulaC4H8N4O4
Average Mass176.1307 Da
Monoisotopic Mass176.05455 Da
IUPAC Name2,2-bis(carbamoylamino)acetic acid
Traditional Nameallantoic acid
CAS Registry Number99-16-1
SMILES
NC(=O)NC(NC(N)=O)C(O)=O
InChI Identifier
InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)
InChI KeyNUCLJNSWZCHRKL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-carbamoyl-alpha amino acids
Alternative Parents
Substituents
  • N-carbamoyl-alpha-amino acid
  • Urea
  • Carbonic acid derivative
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.7 g/LALOGPS
logP-2.1ALOGPS
logP-2.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area147.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.1 m³·mol⁻¹ChemAxon
Polarizability14.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001209
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030673
KNApSAcK IDC00007470
Chemspider ID198
KEGG Compound IDC00499
BioCyc IDALLANTOATE
BiGG IDNot Available
Wikipedia LinkAllantoic_acid
METLIN ID343
PubChem Compound203
PDB IDNot Available
ChEBI ID30837
Good Scents IDrw1216611
References
General References
  1. Collier R, Tegeder M: Soybean ureide transporters play a critical role in nodule development, function and nitrogen export. Plant J. 2012 Nov;72(3):355-67. doi: 10.1111/j.1365-313X.2012.05086.x. Epub 2012 Aug 9. [PubMed:22725647 ]
  2. Bosse MA, Silva MBD, Oliveira NGRM, Araujo MA, Rodrigues C, Azevedo JP, Reis ARD: Physiological impact of flavonoids on nodulation and ureide metabolism in legume plants. Plant Physiol Biochem. 2021 Sep;166:512-521. doi: 10.1016/j.plaphy.2021.06.007. Epub 2021 Jun 16. [PubMed:34171572 ]
  3. Wu T, Zou R, Pu D, Lan Z, Zhao B: Non-targeted and targeted metabolomics profiling of tea plants (Camellia sinensis) in response to its intercropping with Chinese chestnut. BMC Plant Biol. 2021 Jan 21;21(1):55. doi: 10.1186/s12870-021-02841-w. [PubMed:33478393 ]