Cannabis Compound Database: Showing Compound Card for Allantoin (CDB005232)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Created at

2020-04-17 19:22:34 UTC

Updated at

2020-12-07 19:11:48 UTC

CannabisDB ID

CDB005232

Secondary Accession Numbers

Not Available

Cannabis Compound 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. 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. Allantoin is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

158.12

Monoisotopic Molecular Weight

158.044

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

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:

Tissue and substructures:

Placenta

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Personal care products

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	239 °C	Not Available
Boiling Point	478 °C	Wikipedia
Water Solubility	5.26 mg/mL	Not Available
logP	-3.14	Wikipedia

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Putative 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase	PRHOXNB	13q12.2	A6NGE7	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000462

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Enzymes

Enzyme Details

1. Putative 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase

General function:: Not Available
Specific function:: Catalyzes the stereoselective decarboxylation of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline (OHCU) to (S)-allantoin (Potential).
Gene Name:: PRHOXNB
Uniprot ID:: A6NGE7
Molecular weight:: 19129.52

Showing Compound Card for Allantoin (CDB005232)

Structure for CDB005232 (Allantoin)

Enzymes