Allantoin (YMDB00213)

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Identification

YMDB ID

YMDB00213

Name

Allantoin

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

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 in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Allantoin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

CAS number

97-59-6

Weight

Average: 158.1154
Monoisotopic: 158.043990078

InChI Key

POJWUDADGALRAB-UHFFFAOYSA-N

InChI

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)

IUPAC Name

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

Traditional IUPAC Name

allantoin

Chemical Formula

C₄H₆N₄O₃

SMILES

[H]N([H])C(=O)N([H])C1([H])N([H])C(=O)N([H])C1=O

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 )

Physical Properties

State

Solid

Charge

Melting point

239 °C

Experimental Properties

Property	Value	Reference
Water Solubility	5.26 mg/mL [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.73 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

water + Allantoin ↔ Allantoic acid + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

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

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Lawther, R. P., Riemer, E., Chojnacki, B., Cooper, T. G. (1974). "Clustering of the genes for allantoin degradation in Saccharomyces cerevisiae." J Bacteriol 119:461-468.4604238

Synthesis Reference:

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

External Links:

Resource	Link
CHEBI ID	15676
HMDB ID	HMDB00462
Pubchem Compound ID	204
Kegg ID	C01551
ChemSpider ID	199
FOODB ID	FDB001613
Wikipedia	Allantoin
BioCyc ID	R--ALLANTOIN

Enzymes

Protein Details

1. Allantoinase

General function:: Involved in allantoinase activity
Specific function:: Utilization of purines as secondary nitrogen sources, when primary sources are limiting
Gene Name:: DAL1
Uniprot ID:: P32375
Molecular weight:: 50125.89844

Reactions

(S)-allantoin + H(2)O → allantoate.

Transporters

Protein Details

1. Allantoin permease

General function:: Involved in nucleobase transmembrane transporter activity
Specific function:: Transport of allantoin
Gene Name:: DAL4
Uniprot ID:: Q04895
Molecular weight:: 71755.5

Structure for #<Compound:0x9b1c8004>

Enzymes

Reactions

Transporters