Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C4H6N4O3 |
| Molecular Weight | 158.1154 |
| Optical Activity | ( - ) |
| 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 |
|---|---|---|
| The Structure and Function of a Microbial Allantoin Racemase Reveal the Origin and Conservation of a Catalytic Mechanism. | 2016-11-22 |
|
| Reaction Mechanism and Catalytic Fingerprint of Allantoin Racemase. | 2014-07-10 |
|
| The structure of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase provides insights into the mechanism of uric acid degradation. | 2007-06-22 |
|
| Enzymic racemization of allantoin. | 1978-10 |
|
| Allantoin racemase: a new enzyme from Pseudomonas species. | 1975-05-23 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:00:50 GMT 2025
by
admin
on
Mon Mar 31 23:00:50 GMT 2025
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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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439713
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7303-80-2
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DTXSID30904502
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J120C6NTXH
Created by
admin on Mon Mar 31 23:00:50 GMT 2025 , Edited by admin on Mon Mar 31 23:00:50 GMT 2025
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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RACEMATE -> ENANTIOMER |
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