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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:29 UTC
HMDB IDHMDB0001209
Secondary Accession Numbers
  • HMDB01209
Metabolite Identification
Common NameAllantoic acid
DescriptionAllantoic acid, also known as diureidoacetate or allantoate, 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. Allantoic acid exists in all living species, ranging from bacteria to plants to humans. Allantoic acid has been detected, but not quantified in, several different foods, such as peaches (Prunus persica), sea-buckthornberries (Hippophae rhamnoides), garden tomatoes (Solanum lycopersicum), asparagus (Asparagus officinalis), and oats (Avena sativa). This could make allantoic acid a potential biomarker for the consumption of these foods. Allantoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Allantoic acid.
Structure
Data?1582752184
Synonyms
ValueSource
Bis[(aminocarbonyl)amino]acetic acidChEBI
Diureidoacetic acidChEBI
Bis[(aminocarbonyl)amino]acetateGenerator
DiureidoacetateGenerator
AllantoateGenerator
Allantoic acid, monosodium saltMeSH, HMDB
Chemical FormulaC4H8N4O4
Average Molecular Weight176.1307
Monoisotopic Molecular Weight176.054554764
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
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available139.22831661259
DarkChem[M-H]-PredictedNot Available133.04731661259
AllCCS[M+H]+PredictedNot Available140.12132859911
AllCCS[M-H]-PredictedNot Available131.41232859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Allantoic acid,1TMS,#12010.7809https://arxiv.org/abs/1905.12712
Allantoic acid,1TMS,#22111.063https://arxiv.org/abs/1905.12712
Allantoic acid,1TMS,#32053.764https://arxiv.org/abs/1905.12712
Allantoic acid,1TBDMS,#12287.1018https://arxiv.org/abs/1905.12712
Allantoic acid,1TBDMS,#22355.6228https://arxiv.org/abs/1905.12712
Allantoic acid,1TBDMS,#32302.725https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-1900000000-21581f2d921374c163172014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uej-0911000000-7b31dde6fb9c6e9ac1102017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7a-0900000000-d8f1371697a09dc2d0632017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-7557e41727738c553aef2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9800000000-0da9967a35111f5e77c52016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9320000000-3e52483917d7449c6f212017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9500000000-311fe8e2669139e600842012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03k9-9000000000-eb594a4f54a39f5aaad42012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-24cb204bd4d824cf2b532012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-003r-0900000000-91ad7fef4b504549f8492012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9500000000-1f86fa2bb6e6a3e1988e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-6f90d802bf75ec4bc1872012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00dr-9000000000-3900e78a2acf61f39eff2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00dl-9000000000-e98594c1e1b2aa50540a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003r-0900000000-91ad7fef4b504549f8492017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9500000000-1f86fa2bb6e6a3e1988e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-6f90d802bf75ec4bc1872017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-9000000000-3900e78a2acf61f39eff2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9000000000-e98594c1e1b2aa50540a2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-003r-1900000000-e1f2f46a56a37aa069122016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-9600000000-ee4b95c0d08c896e38432016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9300000000-1beb69c57c7dfcea43512016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-682ec8d4340d0075c3692016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5i-9400000000-6faaacd64e9faecfb1bf2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ac2cde105e2954f49b462016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-0900000000-b1ef63ea0c219b928e512021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-8324d5eed9afbe57c6162021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-044i-9200000000-4250c26b69ba807951c72021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00li-9600000000-a27494639afe11d3dd5d2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9100000000-baa27ff86d8c68d59ffe2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c52992021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012646
KNApSAcK IDC00007470
Chemspider ID198
KEGG Compound IDC00499
BioCyc IDALLANTOATE
BiGG IDNot Available
Wikipedia LinkAllantoic_acid
METLIN ID343
PubChem Compound203
PDB IDNot Available
ChEBI ID30837
Food Biomarker OntologyNot Available
VMH IDALLTT
MarkerDB IDNot Available
References
Synthesis ReferenceHermanowicz, Witold. Allantoic acid. Formation of allantoic acid from allantoin. Roczniki Chemii (1948), 22 159-80.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]

Enzymes

General function:
Involved in allantoicase activity
Specific function:
The function of this enzyme is unclear as allantoicase activity is not known to exist in mammals.
Gene Name:
ALLC
Uniprot ID:
Q8N6M5
Molecular weight:
43558.25
Reactions
Allantoic acid + Water → (S)-Ureidoglycolic acid + Ureadetails