Showing metabocard for Allantoin (MMDBc0000347)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:35:50 UTC
Update Date2022-08-31 06:02:29 UTC
Metabolite IDMMDBc0000347
Metabolite Identification
Common NameAllantoin
DescriptionAllantoin is a diureide of glyoxylic acid with the chemical formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a product of the oxidation of uric acid. It is also a product of purine metabolism in most mammals except for higher apes, and it is present in their urine. In humans, uric acid is excreted instead of allantoin. The presence of allantoin in the urine can be an indication of microbial overgrowth or it can be created via non-enzymatic means through high levels of reactive oxygen species. In this regard, allantoin is sometimes used as a marker of oxidative stress. Allantoin can be isolated from cow urine or as a botanical extract of the comfrey plant. It has long been used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulates the growth of healthy tissue. Allantoin can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is frequently present in toothpaste, mouthwash, and other oral hygiene products as well as in shampoos, lipsticks, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products. It is also a metabolite of Bacillus (PMID: 18302748 ) and Streptomyces (PMID: 24292080 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5a8c6ef210>


  Mrv1652307292023482D          

 11 11  0  0  0  0            999 V2000
   -2.1348   -0.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3143   -0.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018    0.5120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7623   -0.8156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0086   -0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7059   -0.8925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203   -0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1348   -0.8925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203    0.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    0.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182    0.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f5a8c6ef210>

HMDB0243717
     RDKit          3D
(S)-(+)-Allantoin
 17 17  0  0  0  0  0  0  0  0999 V2000
   -3.3434    0.1633   -0.0468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0870   -0.4830   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1015   -1.6745   -0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810    0.2106    0.0953 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -0.3822   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717    0.3983   -0.9998 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5209    0.4163   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5316    0.7551   -1.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790   -0.0222    0.8119 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -0.3060    1.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -0.4564    2.3698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -0.1772   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3917    1.0124    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9159    1.2026    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -1.4320   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    0.8857   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531   -0.1106    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10  5  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  9 17  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f5a8c6ef210>


  Mrv1652307292023482D          

 11 11  0  0  0  0            999 V2000
   -2.1348   -0.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3143   -0.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018    0.5120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7623   -0.8156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0086   -0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7059   -0.8925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203   -0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1348   -0.8925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203    0.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    0.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182    0.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000347

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C4H6N4O3

> <MOLECULAR_WEIGHT>
158.1154

> <EXACT_MASS>
158.043990078

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.894797417541849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2,5-dioxoimidazolidin-4-yl)urea

> <ALOGPS_LOGP>
-1.95

> <JCHEM_LOGP>
-2.360540882

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.41419987137925

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.948848806915678

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3762243606061957

> <JCHEM_POLAR_SURFACE_AREA>
113.32

> <JCHEM_REFRACTIVITY>
32.0225

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
allantoin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f5a8c6ef210>

HMDB0243717
     RDKit          3D
(S)-(+)-Allantoin
 17 17  0  0  0  0  0  0  0  0999 V2000
   -3.3434    0.1633   -0.0468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0870   -0.4830   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1015   -1.6745   -0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810    0.2106    0.0953 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -0.3822   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717    0.3983   -0.9998 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5209    0.4163   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5316    0.7551   -1.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790   -0.0222    0.8119 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -0.3060    1.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -0.4564    2.3698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -0.1772   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3917    1.0124    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9159    1.2026    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -1.4320   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    0.8857   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531   -0.1106    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10  5  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  9 17  1  0
M  END
Download

PDB for #<Metabolite:0x00007f5a8c6ef210>

HEADER    PROTEIN                                 29-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUL-20         0                                  
HETATM    1  O   UNK     0      -3.985  -0.539   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.453  -0.378   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.683   0.956   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -1.423  -1.522   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.016  -0.896   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.318  -1.666   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.651  -0.896   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.985  -1.666   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       2.651   0.644   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.177   0.636   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.967   1.666   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   10                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5    3   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f5a8c6ef210>

COMPND    HMDB0000462
HETATM    1  N1  UNL     1       3.091  -0.068   0.934  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.747   0.258   1.218  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.430   0.840   2.277  1.00  0.00           O  
HETATM    4  N2  UNL     1       0.745  -0.079   0.289  1.00  0.00           N  
HETATM    5  C2  UNL     1      -0.662   0.208   0.479  1.00  0.00           C  
HETATM    6  N3  UNL     1      -1.481  -0.952   0.342  1.00  0.00           N  
HETATM    7  C3  UNL     1      -2.009  -0.958  -0.976  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.553  -1.934  -1.560  1.00  0.00           O  
HETATM    9  N4  UNL     1      -1.819   0.349  -1.542  1.00  0.00           N  
HETATM   10  C4  UNL     1      -1.174   1.134  -0.551  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.053   2.402  -0.542  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.522  -0.984   1.190  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.745   0.602   0.441  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.007  -0.562  -0.589  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.780   0.727   1.467  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.664  -1.667   1.066  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.093   0.685  -2.495  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3    4
CONECT    4    5   14
CONECT    5    6   10   15
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    9   10   17
CONECT   10   11   11
END
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SMILES for #<Metabolite:0x00007f5a8c6ef210>

NC(=O)NC1NC(=O)NC1=O
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INCHI for #<Metabolite:0x00007f5a8c6ef210>

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)
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Synonyms
ValueSource
(2,5-Dioxo-4-imidazolidinyl)ureaChEBI
2,5-Dioxo-4-imidazolidinyl-ureaChEBI
4-Ureido-2,5-imidazolidinedioneChEBI
5-Ureido-2,4-imidazolidindioneChEBI
5-UreidohydantoinChEBI
GlyoxyldiureideChEBI
N-(2,5-Dioxo-4-imidazolidinyl)ureaChEBI
(S)-AllantoinHMDB
5-Ureido-hydantoinHMDB
5-UreidohydrantoinHMDB
AlantanHMDB
AllantolHMDB
AlloxantinHMDB
AVC/DienestrolcreamHMDB
CordianineHMDB
D00121HMDB
Fancol toinHMDB
GlyoxyldiureidHMDB
Glyoxylic diureideHMDB
PsoralonHMDB
SebicalHMDB
SeptalanHMDB
Sween brand OF allantoinHMDB
Herpecin-LHMDB
HerpecinLHMDB
Reed and carnrick brand OF allantoinHMDB
Woun'dresHMDB
Allantoin sween brandHMDB
Campbell brand OF allantoinHMDB
Allantoin campbell brandHMDB
Herpecin LHMDB
Molecular FormulaC4H6N4O3
Average Mass158.1154
Monoisotopic Mass158.043990078
IUPAC Name(2,5-dioxoimidazolidin-4-yl)urea
Traditional Nameallantoin
CAS Registry NumberNot Available
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 KeyPOJWUDADGALRAB-UHFFFAOYSA-N