MiMeDB: Showing metabocard for (S)(+)-Allantoin (MMDBc0029955)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:48:13 UTC

Update Date

2022-08-31 17:37:57 UTC

Metabolite ID

MMDBc0029955

Metabolite Identification

Common Name

(S)(+)-Allantoin

Description

Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a diureide of glyoxylic acid. (Wikipedia) In E. coli K-12, the enzyme allantoinase (EC 3.5.2.5) catalyzes the conversion of (S)(+)-Allantoin to Allantoate (KEGG).

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    6    7   12                                             
CONECT    2    1    8    9                                                  
CONECT    3    5    6   10                                                  
CONECT    4    7    8   11                                                  
CONECT    5    3                                                            
CONECT    6    1    3                                                       
CONECT    7    1    4                                                       
CONECT    8    2    4                                                       
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
(S)-Allantoin	ChEBI

Molecular Formula

C₄H₆N₄O₃

Average Mass

158.1154

Monoisotopic Mass

158.043990078

IUPAC Name

N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid

Traditional Name

N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid

CAS Registry Number

97-59-6

SMILES

[H][C@]1(NC(O)=N)N=C(O)N=C1O

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)/t1-/m0/s1

InChI Key

POJWUDADGALRAB-SFOWXEAESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as allantoins. These are heterocyclic compounds containing an imiazolidine ring substituted by a ketone group at positions 2 and 5, and an urea at position 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Allantoins

Alternative Parents

Substituents

Allantoin
Alpha-amino acid or derivatives
5-monosubstituted hydantoin
N-acyl urea
Ureide
Dicarboximide
Carbonic acid derivative
Urea
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ureas (CHEBI:39854 )
imidazolidinone (CHEBI:39854 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.07 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	5.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	121.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44 m³·mol⁻¹	ChemAxon
Polarizability	13.07 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-1900000000-7bd13f672c17d120b1c1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-6900000000-86d834317b3cea626f53	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-e616e553f12597e80e35	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-9600000000-a0c5667d9df61e3f5114	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-9300000000-41072b8960aef6569b10	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-a84520a275e715df81ed	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	30	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Bacteria	Firmicutes	9	Human feces; Human
Bacteria	Deinococcus-thermus	2
Bacteria	Actinobacteria	3
Bacteria	Acidobacteria	1
Eukaryota/Fungi	Ascomycota	1
Archaea/Archaea	Euryarchaeota	2

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02350

BioCyc ID

S-ALLANTOIN

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439714

PDB ID

Not Available

ChEBI ID

15678

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (S)(+)-Allantoin (MMDBc0029955)

MOL for #<Metabolite:0x0000556b6ad1f698>

3D MOL for #<Metabolite:0x0000556b6ad1f698>

3D SDF for #<Metabolite:0x0000556b6ad1f698>

3D-SDF for #<Metabolite:0x0000556b6ad1f698>

PDB for #<Metabolite:0x0000556b6ad1f698>

3D PDB for #<Metabolite:0x0000556b6ad1f698>

SMILES for #<Metabolite:0x0000556b6ad1f698>

INCHI for #<Metabolite:0x0000556b6ad1f698>

Structure for #<Metabolite:0x0000556b6ad1f698>

3D Structure for #<Metabolite:0x0000556b6ad1f698>