AFCDB: Allantoin (FDB001613)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:02 UTC

Update date

2020-09-17 15:41:18 UTC

Primary ID

FDB001613

Secondary Accession Numbers

FDB031153

Chemical Information

FooDB 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. An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen. Allantoin is an extremely weak basic (essentially neutral) compound (based on its pKa). Allantoin exists in all living species, ranging from bacteria to humans. Outside of the human body, Allantoin is found, on average, in the highest concentration within milk (cow) and borages. Allantoin has also been detected, but not quantified in, several different foods, such as sour cherries, italian sweet red peppers, longans, sweet bay, and lambsquarters. This could make allantoin a potential biomarker for the consumption of these foods. Allantoin is a potentially toxic compound.

CAS Number

97-59-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H6N4O3

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

158.1154

Monoisotopic Molecular Weight

158.043990078

Classification

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

Physiological effect

Health effect:

Health condition:

Schizophrenia

Infections and infestations:

Meningitis

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Microbe:

Bacillus:

Bacillus subtilis

Streptomyces:

Streptomyces coelicolor

Plant:

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Personal care products

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	239 oC
Boiling Point	Not Available
Experimental Water Solubility	5.26 mg/mL	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9200000000-5ad052308edfab7b8c5f	2014-09-20	View Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0uds-0911000000-d6d990e16a15b9f27262	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0udi-0920000000-abb5512bfc08cbdd004f	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0f79-0900000000-bf39d4fc494ccd722796	Spectrum
GC-MS	Allantoin, 5 TMS, GC-MS Spectrum	splash10-00kr-4911230000-f2112ac79e45fb821ab6	Spectrum
GC-MS	Allantoin, 4 TMS, GC-MS Spectrum	splash10-0f8i-3933100000-45367e01790bfc8afd6e	Spectrum
GC-MS	Allantoin, 3 TMS, GC-MS Spectrum	splash10-0zfr-4951100000-88808e71aea4d5ad7885	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-5f4cd23ea44234e5a455	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-c9c0d8a7f1e5f105a9c3	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0uds-0911000000-d6d990e16a15b9f27262	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0f79-0900000000-bf39d4fc494ccd722796	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-00kr-4911230000-f2112ac79e45fb821ab6	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0f8i-3933100000-45367e01790bfc8afd6e	Spectrum
GC-MS	Allantoin, non-derivatized, GC-MS Spectrum	splash10-0zfr-4951100000-88808e71aea4d5ad7885	Spectrum
Predicted GC-MS	Allantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0296-9700000000-45ea72c639ca30cd7783	Spectrum
Predicted GC-MS	Allantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-02t9-8900000000-bb0a5fee22239a104e6f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03dj-9000000000-09992debd5f3d399b902	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01oy-9000000000-8fe7df22b2abb81b934a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0006-9100000000-08b1881abaf98821d201	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0006-9100000000-297710f62f9699946151	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-4e30eec1c2a8c4cb7fa8	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-0e0e6cbea70e14292a57	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-d53fc563af9567f05b8a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4c973a5209a8104a49e3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4c973a5209a8104a49e3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-775f532f9c5d9acd1ee6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9400000000-a4e69e926b530e953cc3	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C01551

Pubchem Compound ID

204

Pubchem Substance ID

Not Available

ChEBI ID

15676

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00462

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

ALLANTOIN

BIGG ID

Not Available

KNApSAcK ID

C00007468

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Allantoin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti dandruff			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti peptic			DUKE
anti psoriac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti radicular			DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
keratolytic			DUKE
sunscreen	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
suppurative			DUKE
vulnerary	73336	A drug used in treating and healing of wounds.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Allantoin (FDB001613)

Structure for FDB001613 (Allantoin)