Bovine Metabolome Database: Showing metabocard for Allantoin (BMDB0000462)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:05 UTC

Update Date

2020-06-04 20:51:43 UTC

BMDB ID

BMDB0000462

Secondary Accession Numbers

BMDB00462

Metabolite Identification

Common Name

Allantoin

Description

Allantoin, also known as glyoxyldiureide or 5-ureidohydantoin, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Allantoin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Allantoin exists in all living species, ranging from bacteria to humans. Allantoin is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2,5-Dioxo-4-imidazolidinyl)urea	ChEBI
2,5-Dioxo-4-imidazolidinyl-urea	ChEBI
4-Ureido-2,5-imidazolidinedione	ChEBI
5-Ureido-2,4-imidazolidindione	ChEBI
5-Ureidohydantoin	ChEBI
Glyoxyldiureide	ChEBI
N-(2,5-Dioxo-4-imidazolidinyl)urea	ChEBI
(S)-Allantoin	HMDB
5-Ureido-hydantoin	HMDB
5-Ureidohydrantoin	HMDB
Alantan	HMDB
Allantol	HMDB
Alloxantin	HMDB
AVC/Dienestrolcream	HMDB
Cordianine	HMDB
D00121	HMDB
Fancol toin	HMDB
Glyoxyldiureid	HMDB
Glyoxylic diureide	HMDB
Psoralon	HMDB
Sebical	HMDB
Septalan	HMDB
Sween brand OF allantoin	HMDB
Herpecin-L	HMDB
HerpecinL	HMDB
Reed and carnrick brand OF allantoin	HMDB
Woun'dres	HMDB
Allantoin sween brand	HMDB
Campbell brand OF allantoin	HMDB
Allantoin campbell brand	HMDB
Herpecin L	HMDB

Chemical Formula

C₄H₆N₄O₃

Average Molecular Weight

158.1154

Monoisotopic Molecular Weight

158.043990078

IUPAC Name

(2,5-dioxoimidazolidin-4-yl)urea

Traditional Name

allantoin

CAS Registry Number

97-59-6

SMILES

NC(=O)NC1NC(=O)NC1=O

InChI Identifier

InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)

InChI Key

POJWUDADGALRAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazoles

Alternative Parents

Substituents

Imidazole
Isourea
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ureas (CHEBI:15676 )
imidazolidine-2,4-dione (CHEBI:15676 )
a small molecule (S-ALLANTOIN )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	239 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.26 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2	ALOGPS
logP	-2.4	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	113.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.02 m³·mol⁻¹	ChemAxon
Polarizability	12.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0uds-0911000000-d6d990e16a15b9f27262	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-0920000000-abb5512bfc08cbdd004f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f79-0900000000-bf39d4fc494ccd722796	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-00kr-4911230000-f2112ac79e45fb821ab6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0f8i-3933100000-45367e01790bfc8afd6e	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0zfr-4951100000-88808e71aea4d5ad7885	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-5f4cd23ea44234e5a455	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-c9c0d8a7f1e5f105a9c3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uds-0911000000-d6d990e16a15b9f27262	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f79-0900000000-bf39d4fc494ccd722796	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00kr-4911230000-f2112ac79e45fb821ab6	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f8i-3933100000-45367e01790bfc8afd6e	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfr-4951100000-88808e71aea4d5ad7885	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0296-9700000000-45ea72c639ca30cd7783	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-02t9-8900000000-bb0a5fee22239a104e6f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03dj-9000000000-09992debd5f3d399b902	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01oy-9000000000-8fe7df22b2abb81b934a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9100000000-08b1881abaf98821d201	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0006-9100000000-297710f62f9699946151	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4c973a5209a8104a49e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4c973a5209a8104a49e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9200000000-5ad052308edfab7b8c5f	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Liver
Milk
Placenta
Urine

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24440255	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Milk	Detected and Quantified	205 uM	Not Specified	Not Specified	Normal	PMID: 6539345	details
Milk	Detected and Quantified	198.100 +/- 39 uM	Not Specified	Not Specified	Normal	PMID: 7962859	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22059599	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	All Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	High dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Low dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details

External Links

HMDB ID

HMDB0000462

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Allantoin

METLIN ID

PubChem Compound

204

PDB ID

Not Available

ChEBI ID

15676

References

Synthesis Reference

Du, Niansheng; Yang, Jianhua; Rena, Kasimu. Method for isolation of allantoin from Cistanche deserticola. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 5pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]
Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0. [PubMed:7962859 ]

Showing metabocard for Allantoin (BMDB0000462)

Structure for BMDB0000462 (Allantoin)