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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:48:22 UTC

Update Date

2021-09-26 22:50:40 UTC

HMDB ID

HMDB0243557

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lisofylline

Description

Lisofylline belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Based on a literature review a significant number of articles have been published on Lisofylline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lisofylline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lisofylline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0243557
     RDKit          3D
Lisofylline
 40 41  0  0  0  0  0  0  0  0999 V2000
    5.0068    0.6184    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920   -0.5685    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4379   -1.6598    0.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.8715   -0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.3685   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112    0.2048   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.0647    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290   -0.2210    0.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6887    0.8946    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280    2.0349    0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393    0.7815   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -0.4797   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8734   -0.3030   -0.4506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1539    1.0044   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    1.6978   -0.0314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    3.1371    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585   -1.5702   -0.3423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762   -2.8863   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -1.4406   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309   -2.4074   -0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2211    0.6604    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658    1.5665    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    0.5845    1.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691   -0.3553   -0.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951   -2.2666   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177   -1.6909   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -1.1202    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1886    0.5031   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8481    1.2505   -0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632   -0.5556   -1.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    1.1791   -1.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -1.0304    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    0.7741    1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1598    1.3932   -0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8555    3.5521    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    3.6615   -0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353    3.3187    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -3.4492   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279   -3.4482    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2194   -2.7965   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19  8  1  0
 15 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

  Mrv1572004221605172D          

 20 21  0  0  0  0            999 V2000
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685    2.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    0.5701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    1.9049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 14  8  2  0  0  0  0
 14 11  1  0  0  0  0
 15  2  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  3  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243557

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)CCCCN1C(=O)N(C)C2=C(N(C)C=N2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3

> <INCHI_KEY>
NSMXQKNUPPXBRG-UHFFFAOYSA-N

> <FORMULA>
C13H20N4O3

> <MOLECULAR_WEIGHT>
280.328

> <EXACT_MASS>
280.15354052

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.135604412628485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(5-hydroxyhexyl)-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.2027184959999991

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.68303306498672

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8477735783649373

> <JCHEM_POLAR_SURFACE_AREA>
78.67

> <JCHEM_REFRACTIVITY>
74.65329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lisofylline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243557
     RDKit          3D
Lisofylline
 40 41  0  0  0  0  0  0  0  0999 V2000
    5.0068    0.6184    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920   -0.5685    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4379   -1.6598    0.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.8715   -0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.3685   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112    0.2048   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.0647    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290   -0.2210    0.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6887    0.8946    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280    2.0349    0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393    0.7815   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -0.4797   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8734   -0.3030   -0.4506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1539    1.0044   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    1.6978   -0.0314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    3.1371    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585   -1.5702   -0.3423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762   -2.8863   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -1.4406   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309   -2.4074   -0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2211    0.6604    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658    1.5665    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    0.5845    1.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691   -0.3553   -0.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951   -2.2666   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177   -1.6909   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -1.1202    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1886    0.5031   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8481    1.2505   -0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632   -0.5556   -1.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    1.1791   -1.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -1.0304    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    0.7741    1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1598    1.3932   -0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8555    3.5521    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    3.6615   -0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353    3.3187    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -3.4492   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279   -3.4482    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2194   -2.7965   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19  8  1  0
 15 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.608   5.021   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.037   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -4.132   1.064   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -4.132   3.556   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -1.334   0.770   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   3.080   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   17                                                       
CONECT    8   14   15                                                       
CONECT    9    1    6   18                                                  
CONECT   10   11   12   15                                                  
CONECT   11   10   14   16                                                  
CONECT   12   10   17   19                                                  
CONECT   13   16   17   20                                                  
CONECT   14    8   11                                                       
CONECT   15    2    8   10                                                  
CONECT   16    3   11   13                                                  
CONECT   17    7   12   13                                                  
CONECT   18    9                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0243557
HETATM    1  C1  UNL     1       5.007   0.618   0.949  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.792  -0.568   0.052  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.438  -1.660   0.607  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.307  -0.872  -0.128  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.693   0.369  -0.748  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.211   0.205  -0.982  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.483  -0.065   0.341  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.929  -0.221   0.118  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.689   0.895   0.178  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.228   2.035   0.415  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.039   0.782  -0.029  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.550  -0.480  -0.290  1.00  0.00           C  
HETATM   13  N2  UNL     1      -4.873  -0.303  -0.451  1.00  0.00           N  
HETATM   14  C10 UNL     1      -5.154   1.004  -0.294  1.00  0.00           C  
HETATM   15  N3  UNL     1      -4.030   1.698  -0.031  1.00  0.00           N  
HETATM   16  C11 UNL     1      -3.904   3.137   0.202  1.00  0.00           C  
HETATM   17  N4  UNL     1      -2.759  -1.570  -0.342  1.00  0.00           N  
HETATM   18  C12 UNL     1      -3.276  -2.886  -0.613  1.00  0.00           C  
HETATM   19  C13 UNL     1      -1.436  -1.441  -0.136  1.00  0.00           C  
HETATM   20  O3  UNL     1      -0.631  -2.407  -0.168  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.221   0.660   1.744  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.966   1.567   0.361  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.974   0.584   1.483  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.269  -0.355  -0.933  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.695  -2.267  -0.137  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.218  -1.691  -0.860  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.900  -1.120   0.852  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.189   0.503  -1.730  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.848   1.251  -0.123  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.963  -0.556  -1.733  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.838   1.179  -1.360  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.864  -1.030   0.750  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.725   0.774   1.025  1.00  0.00           H  
HETATM   34  H14 UNL     1      -6.160   1.393  -0.378  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.855   3.552   0.601  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.704   3.662  -0.754  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.135   3.319   0.966  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.500  -3.449  -1.178  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.528  -3.448   0.327  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.219  -2.797  -1.198  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   24
CONECT    3   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9   19
CONECT    9   10   10   11
CONECT   11   12   12   15
CONECT   12   13   17
CONECT   13   14   14
CONECT   14   15   34
CONECT   15   16
CONECT   16   35   36   37
CONECT   17   18   19
CONECT   18   38   39   40
CONECT   19   20   20
END

HMDB0243557
     RDKit          3D
Lisofylline
 40 41  0  0  0  0  0  0  0  0999 V2000
    5.0068    0.6184    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7920   -0.5685    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4379   -1.6598    0.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.8715   -0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.3685   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2112    0.2048   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.0647    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290   -0.2210    0.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6887    0.8946    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280    2.0349    0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393    0.7815   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -0.4797   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8734   -0.3030   -0.4506 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1539    1.0044   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303    1.6978   -0.0314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    3.1371    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585   -1.5702   -0.3423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762   -2.8863   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4356   -1.4406   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309   -2.4074   -0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2211    0.6604    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658    1.5665    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    0.5845    1.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691   -0.3553   -0.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951   -2.2666   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177   -1.6909   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -1.1202    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1886    0.5031   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8481    1.2505   -0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632   -0.5556   -1.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    1.1791   -1.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -1.0304    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247    0.7741    1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1598    1.3932   -0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8555    3.5521    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    3.6615   -0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353    3.3187    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -3.4492   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279   -3.4482    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2194   -2.7965   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19  8  1  0
 15 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,7-Dimethyl-1-(5-hydroxyhexyl)xanthine	HMDB
1-(5R-Hydroxyhexyl)-3,7-dimethylxanthine	HMDB
1-(5'-Hydroxyhexyl)-3,7-dimethylxanthine	HMDB
Lisofylline	MeSH

Chemical Formula

C₁₃H₂₀N₄O₃

Average Molecular Weight

280.328

Monoisotopic Molecular Weight

280.15354052

IUPAC Name

1-(5-hydroxyhexyl)-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

lisofylline

CAS Registry Number

Not Available

SMILES

CC(O)CCCCN1C(=O)N(C)C2=C(N(C)C=N2)C1=O

InChI Identifier

InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3

InChI Key

NSMXQKNUPPXBRG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0243557)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.78	ALOGPS
logP	0.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	17.68	ChemAxon
pKa (Strongest Basic)	-0.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	30.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	166.021	30932474
DeepCCS	[M-H]-	163.663	30932474
DeepCCS	[M-2H]-	196.548	30932474
DeepCCS	[M+Na]+	172.114	30932474
AllCCS	[M+H]+	164.7	32859911
AllCCS	[M+H-H2O]+	161.4	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.7	32859911
AllCCS	[M-H]-	168.5	32859911
AllCCS	[M+Na-2H]-	168.7	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lisofylline	CC(O)CCCCN1C(=O)N(C)C2=C(N(C)C=N2)C1=O	3013.4	Standard polar	33892256
Lisofylline	CC(O)CCCCN1C(=O)N(C)C2=C(N(C)C=N2)C1=O	2386.8	Standard non polar	33892256
Lisofylline	CC(O)CCCCN1C(=O)N(C)C2=C(N(C)C=N2)C1=O	2443.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lisofylline GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9570000000-061a6205dcffb07c754b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisofylline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisofylline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisofylline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 10V, Positive-QTOF	splash10-03di-0090000000-a630b769445418bc0eb3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 20V, Positive-QTOF	splash10-03e9-1490000000-79b1df9e58eed6735082	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 40V, Positive-QTOF	splash10-001i-9410000000-aa0496129f9a65bb8111	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 10V, Negative-QTOF	splash10-004i-0390000000-25edd6d4705fc0e12e09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 20V, Negative-QTOF	splash10-01t9-0690000000-a4ebf3fbf639a03c04af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 40V, Negative-QTOF	splash10-0006-9500000000-fd31b85fdfe514e46508	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 10V, Positive-QTOF	splash10-03e9-0290000000-e608584d9ee60a9733ab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 20V, Positive-QTOF	splash10-001i-0910000000-fa101fd5e3251831bd2d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 40V, Positive-QTOF	splash10-03di-2900000000-2755ad5e6b5927eb35e2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 10V, Negative-QTOF	splash10-004i-0690000000-b6f564aaa7b664cda21a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 20V, Negative-QTOF	splash10-004i-0950000000-cef84386b7d4c5456c8e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisofylline 40V, Negative-QTOF	splash10-055f-5930000000-06f13f0cb946e25b9d16	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

52074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lisofylline

METLIN ID

Not Available

PubChem Compound

57782

PDB ID

Not Available

ChEBI ID

143565

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Lisofylline (HMDB0243557)

MOL for HMDB0243557 (Lisofylline)

3D MOL for HMDB0243557 (Lisofylline)

3D SDF for HMDB0243557 (Lisofylline)

3D-SDF for HMDB0243557 (Lisofylline)

PDB for HMDB0243557 (Lisofylline)

3D PDB for HMDB0243557 (Lisofylline)

SMILES for HMDB0243557 (Lisofylline)

INCHI for HMDB0243557 (Lisofylline)

Structure for HMDB0243557 (Lisofylline)

3D Structure for HMDB0243557 (Lisofylline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra