CAS 97-59-6|allantoin|Glyoxylic(acid) diureide|ALLANTOIN|(2,5-dioxoimidazolidin-4-yl)urea|5-Ureidohydantoin|1-(2,5-dioxoimidazolidin-4-yl)urea|5-脲尿囊素|Glyoxyldiureide|尿囊素|Allantoin|Ureidohydan...

General Information

Structure

Molecular Formula

C₄H₆N₄O₃

Molecular Mass

158.11544

Exact Mass

158.04399007

Charge

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)

InChIKey

POJWUDADGALRAB-UHFFFAOYSA-N

Canonic Smiles

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

Isomeric Smiles

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

Calculated Properties

JChem

LogD (pH = 7.4)

-2.47

LogD (pH = 5.5)

-2.36

Log P

-2.36

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.95

Polar Surface Area

113.32

Polarizability

12.95

Molar Refractivity

32.02

LOG S

-0.27

Data Source

Names and Identifiers

IUPAC Traditional name

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

Synonyms

Glyoxylic(acid) diureideALLANTOIN5-Ureidohydantoin1-(2,5-dioxoimidazolidin-4-yl)urea5-脲尿囊素Glyoxyldiureide尿囊素AllantoinUreidohydantoin尿基间二-氮茂烷-2,4-二酮NSC 7606GlyoxyldiureidSeptalanCordianineSebical(2,5-Dioxo-4-imidazolidinyl)ureaGlyoxylic DiureideAllantolActinac5-Ureido-2,4-imidazolidinedioneDermalexPsoralonAlphosylCordianin(2,5-dioxo-4-imidazolidinyl)urea(2,5-Dioxo-4-imidazolidinyl)ureaGlyoxyldiureide4-ureido-2,5-imidazolidinedione5-Ureido-2,4-imidazolidindione2,5-Dioxo-4-imidazolidinyl-ureaallantoinAllantoinN-(2,5-Dioxo-4-imidazolidinyl)ureaallantoin5-Ureidohydantoin

IUPAC name

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

Names and Identifiers

Registration numbers

EC Number

CAS Number

Beilstein Number

MDL Number

PubChem SID

162089975248458638143386

PubChem CID

Registration numbers

Properties

Pharmacology Properties

Mechanism of Action

Cell proliferation promoter.

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02100379

Crystalline

05206440

MP Biomedicals Rare Chemical collection

Wikipedia

Allantoin

Sigma Aldrich

A7878

Biochem/physiol Actions
通过尿酸途径的嘌呤代谢物。尿酸也可与自由基反应生成尿囊素，因此尿囊素可作为氧化应激反应的有效生物标记。

93791

Biochem/physiol Actions
Purine metabolite via the uric acid pathway. Uric acid also reacts with free radicals to produce allantoin, thus allantoin may be a useful biomarker for oxidative stress.

05670

Biochem/physiol Actions
Purine metabolite via the uric acid pathway. Uric acid also reacts with free radicals to produce allantoin, thus allantoin may be a useful biomarker for oxidative stress.
Application
Reactant for: Synthesis of Mannich bases for use as antibacterial agents1 Synthesis of sulofenur analogs for use as antitumor agents2

TRC

A540500

Vulnerary; debriding agent. Purine metabolite via the uric acid pathway.

ChEBI

CHEBI:15676

An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen.

Molecule Details

References

PubChem Literature

From Data Sources

• Moriwaki, Y., et al., Histol. Histopathol., 14, 1321(1999).

• Vissers, S., et al.: Eur. J. Biochem., 181, 357 (1989)

• Skinner, K., et al.: J. Biol. Chem., 273, 24491 (1989)

• Baars, J., et al.: Microbiology 140, 1161 (1989)

• Org. Synth., 1933, 13, 1, (synth, bibl)

• Abblard, J. et al., Bull. Soc. Chim. Fr., 1971, 942, (struct)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 184

• U.S. Pat., 1956, 2 761 867; CA, 51, 3668i, (synth, Al compds)

• Fosse, R. et al., C. R. Hebd. Seances Acad. Sci., 1934, 98, 689; 1374; 1953, (isol, resoln)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 809A, (ir)

• Biltz, H., Ber., 1911, 44, 282, (derivs)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 754; 755

• Gravenmade, E.J. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1969, 88, 929, (resoln)

• Greenbaum, F.R., Am. J. Pharm., 1940, 112, 205, (rev)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1316C, (nmr)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 2569, (occur)

• U.S. Pat., 1967, 3 305 557; CA, 66, 85787x, (synth)

• Coxon, B. et al., J.O.C., 1977, 42, 3132, (cmr)

• Mecca, S.B., Soap, Perfum. Cosmet., 1976, 49, 434, (rev)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

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

Synonyms

IUPAC name

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

Molecule Details

MP Biomedicals

02100379

Crystalline

05206440

MP Biomedicals Rare Chemical collection

Wikipedia

Allantoin

Sigma Aldrich

A7878

Biochem/physiol Actions
通过尿酸途径的嘌呤代谢物。尿酸也可与自由基反应生成尿囊素，因此尿囊素可作为氧化应激反应的有效生物标记。

93791

Biochem/physiol Actions
Purine metabolite via the uric acid pathway. Uric acid also reacts with free radicals to produce allantoin, thus allantoin may be a useful biomarker for oxidative stress.

05670

TRC

A540500

Vulnerary; debriding agent. Purine metabolite via the uric acid pathway.

ChEBI

CHEBI:15676

An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen.

References

PubChem Literature

From Data Sources

• Moriwaki, Y., et al., Histol. Histopathol., 14, 1321(1999).

• Vissers, S., et al.: Eur. J. Biochem., 181, 357 (1989)