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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
Structure of ALLANTOIN, (-)-

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

HIDE SMILES / InChI

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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: UniProtKB - E3SAZ9 (Allantoin racemase)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Allantoin racemase: a new enzyme from Pseudomonas species.
1975 May 23
The structure of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase provides insights into the mechanism of uric acid degradation.
2007 Jun 22
The Structure and Function of a Microbial Allantoin Racemase Reveal the Origin and Conservation of a Catalytic Mechanism.
2016 Nov 22

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:05:02 GMT 2023
Edited
by admin
on Sat Dec 16 10:05:02 GMT 2023
Record UNII
J120C6NTXH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALLANTOIN, (-)-
Common Name English
ALLANTOIN, (R)-(-)-
Common Name English
(-)-ALLANTOIN
Common Name English
UREA, N-((4R)-2,5-DIOXO-4-IMIDAZOLIDINYL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
439713
Created by admin on Sat Dec 16 10:05:02 GMT 2023 , Edited by admin on Sat Dec 16 10:05:02 GMT 2023
PRIMARY
CAS
7303-80-2
Created by admin on Sat Dec 16 10:05:02 GMT 2023 , Edited by admin on Sat Dec 16 10:05:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID30904502
Created by admin on Sat Dec 16 10:05:02 GMT 2023 , Edited by admin on Sat Dec 16 10:05:02 GMT 2023
PRIMARY
FDA UNII
J120C6NTXH
Created by admin on Sat Dec 16 10:05:02 GMT 2023 , Edited by admin on Sat Dec 16 10:05:02 GMT 2023
PRIMARY