Np mrd loader

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Record Information
Version1.0
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
Thumb
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Chlamydomonas reinhardtiiKNApSAcK Database
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Corylus avellanaFooDB
Foeniculum vulgareKNApSAcK Database
Glycine maxKNApSAcK Database
Lupinus albusFooDB
Phaseolus vulgarisFooDB
Robinia pseudoacaciaKNApSAcK Database
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
logP10(-2.1) g/LALOGPS
logP10(-2.6) g/LChemAxon
logS10(-1.4) g/LALOGPS
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. Vigetti D, Pollegioni L, Monetti C, Prati M, Bernardini G, Gornati R: Property comparison of recombinant amphibian and mammalian allantoicases. FEBS Lett. 2002 Feb 13;512(1-3):323-8. [PubMed:11852104 ]
  2. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]