T3DB: Allantoin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2014-09-11 05:23:11 UTC

Update Date

2014-12-24 20:27:00 UTC

Accession Number

T3D4936

Identification

Common Name

Allantoin

Class

Small Molecule

Description

Allantoin is a diureide of glyoxylic acid with the chemical formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a product of purine metabolism in most mammals except higher apes, and it is present in their urine. In humans, uric acid is excreted instead of allantoin. The presence of allantoin in the urine can be an indication of microbial overgrowth or it can be created via non-enzymatic means through high levels of reactive oxygen species. In this regard Allantoin is sometimes used as a marker of oxidative stress. Allantoin can be isolated from cow urine or as a botanical extract of the comfrey plant. It has long been used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulates the growth of healthy tissue. Allantoin can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is frequently present in toothpaste, mouthwash, and other oral hygiene products as well as shampoos, lipsticks, various cosmetic lotions and creams and other cosmetic and pharmaceutical products.

Compound Type

Amide
Amine
Animal Toxin
Cosmetic Toxin
Food Toxin
Household Toxin
Mammal Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
(S)-allantoin
2,5-Dioxo-4-imidazolidinyl-urea
4-Ureido-2,5-Imidazolidinedione
5-Ureido-Hydantoin
5-Ureidohydantoin
5-Ureidohydrantoin
Alantan
Allantol
Alloxantin
AVC/Dienestrolcream
Cordianine
D00121
Fancol TOIN
Glyoxyldiureid
Glyoxyldiureide
Glyoxylic diureide
N-(2,5-Dioxo-4-imidazolidinyl)urea
Psoralon
Sebical
Septalan

Chemical Formula

C₄H₆N₄O₃

Average Molecular Mass

158.115 g/mol

Monoisotopic Mass

158.044 g/mol

CAS Registry Number

97-59-6

IUPAC Name

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

Traditional Name

allantoin

SMILES

OC(=N)NC1N=C(O)N=C1O

InChI Identifier

InChI=1/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

InChIKey=POJWUDADGALRAB-UHFFFAOYNA-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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

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

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-0920000000-abb5512bfc08cbdd004f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f79-0900000000-bf39d4fc494ccd722796	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-00kr-4911230000-f2112ac79e45fb821ab6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0f8i-3933100000-45367e01790bfc8afd6e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0zfr-4951100000-88808e71aea4d5ad7885	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-5f4cd23ea44234e5a455	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-c9c0d8a7f1e5f105a9c3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uds-0911000000-d6d990e16a15b9f27262	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f79-0900000000-bf39d4fc494ccd722796	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00kr-4911230000-f2112ac79e45fb821ab6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f8i-3933100000-45367e01790bfc8afd6e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfr-4951100000-88808e71aea4d5ad7885	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0296-9700000000-45ea72c639ca30cd7783	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-02t9-8900000000-bb0a5fee22239a104e6f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03dj-9000000000-09992debd5f3d399b902	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01oy-9000000000-8fe7df22b2abb81b934a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9100000000-08b1881abaf98821d201	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0006-9100000000-297710f62f9699946151	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4c973a5209a8104a49e3	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4c973a5209a8104a49e3	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9200000000-5ad052308edfab7b8c5f	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB00462

PubChem Compound ID

204

ChEMBL ID

Not Available

ChemSpider ID

199

KEGG ID

C01551

UniProt ID

Not Available

OMIM ID

ChEBI ID

15676

BioCyc ID

R--ALLANTOIN

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Allantoin

References

Synthesis Reference

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

MSDS

Link

General References

Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. [11805243 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [12829005 ]
Lagendijk J, Ubbink JB, Vermaak WJ: The determination of allantoin, a possible indicator of oxidant status, in human plasma. J Chromatogr Sci. 1995 Apr;33(4):186-93. [7738135 ]
Goldman SC, Holcenberg JS, Finklestein JZ, Hutchinson R, Kreissman S, Johnson FL, Tou C, Harvey E, Morris E, Cairo MS: A randomized comparison between rasburicase and allopurinol in children with lymphoma or leukemia at high risk for tumor lysis. Blood. 2001 May 15;97(10):2998-3003. [11342423 ]
Kand'ar R, Zakova P, Muzakova V: Monitoring of antioxidant properties of uric acid in humans for a consideration measuring of levels of allantoin in plasma by liquid chromatography. Clin Chim Acta. 2006 Mar;365(1-2):249-56. Epub 2005 Sep 27. [16194528 ]
Pavitt DV, de Fonseka S, Al-Khalaf N, Cam JM, Reaveley DA: Assay of serum allantoin in humans by gas chromatography-mass spectrometry. Clin Chim Acta. 2002 Apr;318(1-2):63-70. [11880113 ]
Alfazema LN, Howells S, Perrett D: Determination of allantoin in biofluids using micellar electrokinetic capillary chromatography. J Chromatogr A. 1998 Aug 21;817(1-2):345-52. [9764504 ]
Becker BF, Kastenbauer S, Kodel U, Kiesl D, Pfister HW: Urate oxidation in CSF and blood of patients with inflammatory disorders of the nervous system. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1201-4. [15571231 ]
Grootveld M, Halliwell B: Measurement of allantoin and uric acid in human body fluids. A potential index of free-radical reactions in vivo? Biochem J. 1987 May 1;243(3):803-8. [3663100 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Nuclear receptor subfamily 1 group I member 2

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular Weight:: 49761.245 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	2.92 uM	ATG_PXR_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

2. Peroxisome proliferator-activated receptor alpha

General Function:: Zinc ion binding
Specific Function:: Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:: PPARA
Uniprot ID:: Q07869
Molecular Weight:: 52224.595 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.22 uM	ATG_PPARa_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Allantoin (T3D4936)

Structure for T3D4936: Allantoin

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References