Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C4H6N4O3 |
Molecular Weight | 158.1154 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)N[C@@H]1NC(=O)NC1=O
InChI
InChIKey=POJWUDADGALRAB-PVQJCKRUSA-N
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-/m1/s1
Molecular Formula | C4H6N4O3 |
Molecular Weight | 158.1154 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Allantoin is a product of adenine and guanine metabolism. Allantoin exists as two enantiomers (R)-(-)-allantoin and (S)-(+)-allantoin that are subject to enzimatic racemization. The spontaneous decomposition of upstream intermediates and the nonenzymatic racemization of allantoin lead to an accumulation of (R)-allantoin, because the enzymes converting allantoin into allantoate are specific for the (S) isomer. The enzyme allantoin racemase catalyzes the reversible conversion between the two allantoin enantiomers, thus ensuring the overall efficiency of the catabolic pathway and preventing allantoin accumulation. The naturally-occurring (+)-allantoin was isolated from leaves of Platanus orientah and from the urine of cattle. (-)-Allantoin was obtained by degradation of the dextrorotatory form of the racemate by allantoinase from soy bean meal or from the liver of Raja clavata.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: UniProtKB - E3SAZ9 (Allantoin racemase) Sources: https://www.ncbi.nlm.nih.gov/pubmed/237557 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Allantoin racemase: a new enzyme from Pseudomonas species. | 1975 May 23 |
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The structure of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase provides insights into the mechanism of uric acid degradation. | 2007 Jun 22 |
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The Structure and Function of a Microbial Allantoin Racemase Reveal the Origin and Conservation of a Catalytic Mechanism. | 2016 Nov 22 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:05:02 GMT 2023
by
admin
on
Sat Dec 16 10:05:02 GMT 2023
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Record UNII |
J120C6NTXH
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Record Status |
Validated (UNII)
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Record Version |
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-
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DTXSID30904502
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J120C6NTXH
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