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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:19:16 UTC

Update Date

2021-09-26 23:10:32 UTC

HMDB ID

HMDB0255580

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Niceritrol

Description

Niceritrol, also known as perycit, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Niceritrol is a strong basic compound (based on its pKa). Niceritrol is a niacin derivative used as a hypolipidemic agent. This compound has been identified in human blood as reported by (PMID: 31557052 ). Niceritrol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Niceritrol 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

  Mrv1572004221603202D          

 41 44  0  0  0  0            999 V2000
    0.7441    2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7441    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8875   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.3941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6500   -4.8908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    2.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  5  1  2  0  0  0  0
  6  2  2  0  0  0  0
  7  3  2  0  0  0  0
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  9  1  1  0  0  0  0
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 40 27  1  0  0  0  0
 41 20  1  0  0  0  0
 41 28  1  0  0  0  0
M  END

HMDB0255580
     RDKit          3D
Niceritrol
 65 68  0  0  0  0  0  0  0  0999 V2000
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    4.0102   -3.0061   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8773   -2.0512   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
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 41 65  1  0
M  END

  Mrv1572004221603202D          

 41 44  0  0  0  0            999 V2000
    0.7441    2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 27 23  1  0  0  0  0
 28 24  1  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
 30  9  2  0  0  0  0
 30 13  1  0  0  0  0
 31 10  2  0  0  0  0
 31 14  1  0  0  0  0
 32 11  2  0  0  0  0
 32 15  1  0  0  0  0
 33 12  2  0  0  0  0
 33 16  1  0  0  0  0
 34 25  2  0  0  0  0
 35 26  2  0  0  0  0
 36 27  2  0  0  0  0
 37 28  2  0  0  0  0
 38 17  1  0  0  0  0
 38 25  1  0  0  0  0
 39 18  1  0  0  0  0
 39 26  1  0  0  0  0
 40 19  1  0  0  0  0
 40 27  1  0  0  0  0
 41 20  1  0  0  0  0
 41 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255580

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(OCC(COC(=O)C1=CN=CC=C1)(COC(=O)C1=CN=CC=C1)COC(=O)C1=CN=CC=C1)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H24N4O8/c34-25(21-5-1-9-30-13-21)38-17-29(18-39-26(35)22-6-2-10-31-14-22,19-40-27(36)23-7-3-11-32-15-23)20-41-28(37)24-8-4-12-33-16-24/h1-16H,17-20H2

> <INCHI_KEY>
KUEUWHJGRZKESU-UHFFFAOYSA-N

> <FORMULA>
C29H24N4O8

> <MOLECULAR_WEIGHT>
556.531

> <EXACT_MASS>
556.159413749

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
55.543604695122724

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(pyridine-3-carbonyloxy)-2,2-bis[(pyridine-3-carbonyloxy)methyl]propyl pyridine-3-carboxylate

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
2.371923174

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.8448178471763206

> <JCHEM_POLAR_SURFACE_AREA>
156.75999999999993

> <JCHEM_REFRACTIVITY>
142.38809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bufor

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255580
     RDKit          3D
Niceritrol
 65 68  0  0  0  0  0  0  0  0999 V2000
    0.6707   -1.8634   -2.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -1.0616   -3.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    0.1422   -2.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    0.7345   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539    0.1681   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -1.2172    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469   -1.4638   -0.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6091   -2.7085   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -3.6328    0.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -3.0061   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8773   -2.0512   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1894   -2.3540   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6949   -3.6301   -0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8331   -4.5522   -0.2953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310   -4.2635   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9822    1.0597    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4023    2.3321    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    3.3163    1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8484    3.0411    2.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3176    4.6468    1.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270    4.9515    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    6.2283    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    7.1543    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976    6.8698    2.4126 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075    5.6262    2.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402    0.3030    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -0.2140    1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.1548    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939    0.3381    1.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1560   -0.6572    3.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320   -1.2091    4.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756   -1.6558    5.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990   -1.5640    5.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822   -1.0183    4.8115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4641   -0.5792    3.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435   -1.4897   -4.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201   -0.6223   -4.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780   -1.0521   -5.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8257   -2.3012   -6.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -3.1340   -5.7980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047   -2.7373   -4.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170    1.8089   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4744    0.9010   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095   -2.0223   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -1.3051    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5368   -1.0506   -0.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628   -1.6029   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7396   -3.8314   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9091   -5.0674    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    1.0486    0.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8415    0.5589    1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924    4.1696    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741    6.4582    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    8.1428    1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229    5.3922    3.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8470   -0.2093   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836    1.3839    0.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.2692    3.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262   -2.0908    5.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091   -1.9227    6.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2405   -0.1490    2.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654    0.3641   -4.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753   -0.4017   -5.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017   -2.6392   -7.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -3.3849   -4.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
  2 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 15 10  1  0
 25 20  1  0
 35 30  1  0
 41 36  1  0
  4 42  1  0
  4 43  1  0
  6 44  1  0
  6 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 31 58  1  0
 32 59  1  0
 33 60  1  0
 35 61  1  0
 37 62  1  0
 38 63  1  0
 39 64  1  0
 41 65  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       1.389   4.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.391  -9.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.390  -7.796   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.390   2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.389   2.929   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.391  -7.851   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620  -6.462   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.160   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.723   5.239   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.057 -10.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620  -9.129   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.160   4.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.056   2.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724  -7.851   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.310  -7.796   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.470   2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.056  -1.691   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.620  -3.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.160  -1.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.723   2.159   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.057  -7.081   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -6.462   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.700   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.723   0.619   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.057  -5.541   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.310  -5.128   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.470   0.206   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.390  -2.461   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       4.056   4.469   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       6.724  -9.391   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       3.080  -9.129   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       7.700   4.207   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0       1.389  -0.151   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.391  -4.771   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.770  -5.128   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.010   0.206   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.056  -0.151   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       6.724  -4.771   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       3.080  -3.795   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.700  -1.127   0.000  0.00  0.00           O+0
CONECT    1    5    9                                                       
CONECT    2    6   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   12                                                       
CONECT    5    1   21                                                       
CONECT    6    2   22                                                       
CONECT    7    3   23                                                       
CONECT    8    4   24                                                       
CONECT    9    1   30                                                       
CONECT   10    2   31                                                       
CONECT   11    3   32                                                       
CONECT   12    4   33                                                       
CONECT   13   21   30                                                       
CONECT   14   22   31                                                       
CONECT   15   23   32                                                       
CONECT   16   24   33                                                       
CONECT   17   29   38                                                       
CONECT   18   29   39                                                       
CONECT   19   29   40                                                       
CONECT   20   29   41                                                       
CONECT   21    5   13   25                                                  
CONECT   22    6   14   26                                                  
CONECT   23    7   15   27                                                  
CONECT   24    8   16   28                                                  
CONECT   25   21   34   38                                                  
CONECT   26   22   35   39                                                  
CONECT   27   23   36   40                                                  
CONECT   28   24   37   41                                                  
CONECT   29   17   18   19   20                                             
CONECT   30    9   13                                                       
CONECT   31   10   14                                                       
CONECT   32   11   15                                                       
CONECT   33   12   16                                                       
CONECT   34   25                                                            
CONECT   35   26                                                            
CONECT   36   27                                                            
CONECT   37   28                                                            
CONECT   38   17   25                                                       
CONECT   39   18   26                                                       
CONECT   40   19   27                                                       
CONECT   41   20   28                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

COMPND    HMDB0255580
HETATM    1  O1  UNL     1       0.671  -1.863  -2.825  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.217  -1.062  -3.172  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.330   0.142  -2.599  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.382   0.735  -1.606  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.254   0.168  -0.242  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.658  -1.217   0.039  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.047  -1.464  -0.228  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.609  -2.709  -0.023  1.00  0.00           C  
HETATM    9  O4  UNL     1       1.877  -3.633   0.405  1.00  0.00           O  
HETATM   10  C6  UNL     1       4.010  -3.006  -0.279  1.00  0.00           C  
HETATM   11  C7  UNL     1       4.877  -2.051  -0.748  1.00  0.00           C  
HETATM   12  C8  UNL     1       6.189  -2.354  -0.981  1.00  0.00           C  
HETATM   13  C9  UNL     1       6.695  -3.630  -0.754  1.00  0.00           C  
HETATM   14  N1  UNL     1       5.833  -4.552  -0.295  1.00  0.00           N  
HETATM   15  C10 UNL     1       4.531  -4.264  -0.061  1.00  0.00           C  
HETATM   16  C11 UNL     1       0.982   1.060   0.776  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.402   2.332   0.739  1.00  0.00           O  
HETATM   18  C12 UNL     1       0.891   3.316   1.572  1.00  0.00           C  
HETATM   19  O6  UNL     1       1.848   3.041   2.346  1.00  0.00           O  
HETATM   20  C13 UNL     1       0.318   4.647   1.564  1.00  0.00           C  
HETATM   21  C14 UNL     1      -0.727   4.951   0.721  1.00  0.00           C  
HETATM   22  C15 UNL     1      -1.262   6.228   0.727  1.00  0.00           C  
HETATM   23  C16 UNL     1      -0.719   7.154   1.588  1.00  0.00           C  
HETATM   24  N2  UNL     1       0.298   6.870   2.413  1.00  0.00           N  
HETATM   25  C17 UNL     1       0.808   5.626   2.397  1.00  0.00           C  
HETATM   26  C18 UNL     1      -1.240   0.303   0.121  1.00  0.00           C  
HETATM   27  O7  UNL     1      -1.470  -0.214   1.417  1.00  0.00           O  
HETATM   28  C19 UNL     1      -2.799  -0.155   1.881  1.00  0.00           C  
HETATM   29  O8  UNL     1      -3.694   0.338   1.148  1.00  0.00           O  
HETATM   30  C20 UNL     1      -3.156  -0.657   3.200  1.00  0.00           C  
HETATM   31  C21 UNL     1      -2.232  -1.209   4.056  1.00  0.00           C  
HETATM   32  C22 UNL     1      -2.676  -1.656   5.286  1.00  0.00           C  
HETATM   33  C23 UNL     1      -3.999  -1.564   5.671  1.00  0.00           C  
HETATM   34  N3  UNL     1      -4.882  -1.018   4.812  1.00  0.00           N  
HETATM   35  C24 UNL     1      -4.464  -0.579   3.610  1.00  0.00           C  
HETATM   36  C25 UNL     1      -1.144  -1.490  -4.243  1.00  0.00           C  
HETATM   37  C26 UNL     1      -2.120  -0.622  -4.633  1.00  0.00           C  
HETATM   38  C27 UNL     1      -2.978  -1.052  -5.644  1.00  0.00           C  
HETATM   39  C28 UNL     1      -2.826  -2.301  -6.207  1.00  0.00           C  
HETATM   40  N4  UNL     1      -1.849  -3.134  -5.798  1.00  0.00           N  
HETATM   41  C29 UNL     1      -1.005  -2.737  -4.818  1.00  0.00           C  
HETATM   42  H1  UNL     1      -0.017   1.809  -1.513  1.00  0.00           H  
HETATM   43  H2  UNL     1       1.474   0.901  -1.882  1.00  0.00           H  
HETATM   44  H3  UNL     1       0.010  -2.022  -0.293  1.00  0.00           H  
HETATM   45  H4  UNL     1       0.630  -1.305   1.192  1.00  0.00           H  
HETATM   46  H5  UNL     1       4.537  -1.051  -0.939  1.00  0.00           H  
HETATM   47  H6  UNL     1       6.863  -1.603  -1.348  1.00  0.00           H  
HETATM   48  H7  UNL     1       7.740  -3.831  -0.950  1.00  0.00           H  
HETATM   49  H8  UNL     1       3.909  -5.067   0.308  1.00  0.00           H  
HETATM   50  H9  UNL     1       2.062   1.049   0.520  1.00  0.00           H  
HETATM   51  H10 UNL     1       0.842   0.559   1.759  1.00  0.00           H  
HETATM   52  H11 UNL     1      -1.092   4.170   0.080  1.00  0.00           H  
HETATM   53  H12 UNL     1      -2.074   6.458   0.069  1.00  0.00           H  
HETATM   54  H13 UNL     1      -1.139   8.143   1.587  1.00  0.00           H  
HETATM   55  H14 UNL     1       1.623   5.392   3.056  1.00  0.00           H  
HETATM   56  H15 UNL     1      -1.847  -0.209  -0.650  1.00  0.00           H  
HETATM   57  H16 UNL     1      -1.484   1.384   0.058  1.00  0.00           H  
HETATM   58  H17 UNL     1      -1.208  -1.269   3.732  1.00  0.00           H  
HETATM   59  H18 UNL     1      -1.926  -2.091   5.951  1.00  0.00           H  
HETATM   60  H19 UNL     1      -4.309  -1.923   6.638  1.00  0.00           H  
HETATM   61  H20 UNL     1      -5.240  -0.149   2.969  1.00  0.00           H  
HETATM   62  H21 UNL     1      -2.265   0.364  -4.211  1.00  0.00           H  
HETATM   63  H22 UNL     1      -3.775  -0.402  -5.995  1.00  0.00           H  
HETATM   64  H23 UNL     1      -3.502  -2.639  -7.003  1.00  0.00           H  
HETATM   65  H24 UNL     1      -0.201  -3.385  -4.460  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   36
CONECT    3    4
CONECT    4    5   42   43
CONECT    5    6   16   26
CONECT    6    7   44   45
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   46
CONECT   12   13   13   47
CONECT   13   14   48
CONECT   14   15   15
CONECT   15   49
CONECT   16   17   50   51
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   21   25
CONECT   21   22   52
CONECT   22   23   23   53
CONECT   23   24   54
CONECT   24   25   25
CONECT   25   55
CONECT   26   27   56   57
CONECT   27   28
CONECT   28   29   29   30
CONECT   30   31   31   35
CONECT   31   32   58
CONECT   32   33   33   59
CONECT   33   34   60
CONECT   34   35   35
CONECT   35   61
CONECT   36   37   37   41
CONECT   37   38   62
CONECT   38   39   39   63
CONECT   39   40   64
CONECT   40   41   41
CONECT   41   65
END

HMDB0255580
     RDKit          3D
Niceritrol
 65 68  0  0  0  0  0  0  0  0999 V2000
    0.6707   -1.8634   -2.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -1.0616   -3.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    0.1422   -2.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817    0.7345   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539    0.1681   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -1.2172    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469   -1.4638   -0.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6091   -2.7085   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -3.6328    0.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -3.0061   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8773   -2.0512   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1894   -2.3540   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6949   -3.6301   -0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8331   -4.5522   -0.2953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310   -4.2635   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9822    1.0597    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4023    2.3321    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    3.3163    1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8484    3.0411    2.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3176    4.6468    1.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270    4.9515    0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    6.2283    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    7.1543    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976    6.8698    2.4126 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075    5.6262    2.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402    0.3030    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -0.2140    1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -0.1548    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939    0.3381    1.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1560   -0.6572    3.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320   -1.2091    4.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756   -1.6558    5.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990   -1.5640    5.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822   -1.0183    4.8115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4641   -0.5792    3.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435   -1.4897   -4.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201   -0.6223   -4.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780   -1.0521   -5.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8257   -2.3012   -6.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491   -3.1340   -5.7980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047   -2.7373   -4.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170    1.8089   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4744    0.9010   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095   -2.0223   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -1.3051    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5368   -1.0506   -0.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628   -1.6029   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7396   -3.8314   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9091   -5.0674    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    1.0486    0.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8415    0.5589    1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924    4.1696    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741    6.4582    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    8.1428    1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229    5.3922    3.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8470   -0.2093   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836    1.3839    0.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.2692    3.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262   -2.0908    5.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091   -1.9227    6.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2405   -0.1490    2.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654    0.3641   -4.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753   -0.4017   -5.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017   -2.6392   -7.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -3.3849   -4.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
  2 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 15 10  1  0
 25 20  1  0
 35 30  1  0
 41 36  1  0
  4 42  1  0
  4 43  1  0
  6 44  1  0
  6 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 31 58  1  0
 32 59  1  0
 33 60  1  0
 35 61  1  0
 37 62  1  0
 38 63  1  0
 39 64  1  0
 41 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Perycit	Kegg
Niceritrol tetrahydrochloride	MeSH
Pentaerythritol tetranicotinate	MeSH
Pentaerythritoltetranicotinate	MeSH
Tetrahydrochloride, niceritrol	MeSH
Tetranicotinate, pentaerythritol	MeSH
3-(Pyridine-3-carbonyloxy)-2,2-bis[(pyridine-3-carbonyloxy)methyl]propyl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₂₉H₂₄N₄O₈

Average Molecular Weight

556.531

Monoisotopic Molecular Weight

556.159413749

IUPAC Name

3-(pyridine-3-carbonyloxy)-2,2-bis[(pyridine-3-carbonyloxy)methyl]propyl pyridine-3-carboxylate

Traditional Name

bufor

CAS Registry Number

Not Available

SMILES

O=C(OCC(COC(=O)C1=CN=CC=C1)(COC(=O)C1=CN=CC=C1)COC(=O)C1=CN=CC=C1)C1=CN=CC=C1

InChI Identifier

InChI=1S/C29H24N4O8/c34-25(21-5-1-9-30-13-21)38-17-29(18-39-26(35)22-6-2-10-31-14-22,19-40-27(36)23-7-3-11-32-15-23)20-41-28(37)24-8-4-12-33-16-24/h1-16H,17-20H2

InChI Key

KUEUWHJGRZKESU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Heteroaromatic compound
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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: HMDB0255580)

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	1.88	ALOGPS
logP	2.37	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	3.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	156.76 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	142.39 m³·mol⁻¹	ChemAxon
Polarizability	55.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	220.56	30932474
DeepCCS	[M-H]-	218.164	30932474
DeepCCS	[M-2H]-	251.048	30932474
DeepCCS	[M+Na]+	226.472	30932474
AllCCS	[M+H]+	225.8	32859911
AllCCS	[M+H-H2O]+	224.2	32859911
AllCCS	[M+NH4]+	227.2	32859911
AllCCS	[M+Na]+	227.6	32859911
AllCCS	[M-H]-	215.2	32859911
AllCCS	[M+Na-2H]-	216.2	32859911
AllCCS	[M+HCOO]-	217.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Niceritrol	O=C(OCC(COC(=O)C1=CN=CC=C1)(COC(=O)C1=CN=CC=C1)COC(=O)C1=CN=CC=C1)C1=CN=CC=C1	5889.8	Standard polar	33892256
Niceritrol	O=C(OCC(COC(=O)C1=CN=CC=C1)(COC(=O)C1=CN=CC=C1)COC(=O)C1=CN=CC=C1)C1=CN=CC=C1	4198.2	Standard non polar	33892256
Niceritrol	O=C(OCC(COC(=O)C1=CN=CC=C1)(COC(=O)C1=CN=CC=C1)COC(=O)C1=CN=CC=C1)C1=CN=CC=C1	4517.8	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niceritrol 10V, Positive-QTOF	splash10-0a4i-0000090000-3b715d2b91a75cb056e9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niceritrol 20V, Positive-QTOF	splash10-0a4i-0000190000-beb462a2fde6b606db38	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niceritrol 40V, Positive-QTOF	splash10-0pc0-9831430000-43bc086d41cfc677e28f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niceritrol 10V, Negative-QTOF	splash10-0a4i-0000090000-57703f91d2243ca067aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niceritrol 20V, Negative-QTOF	splash10-0a4i-0000090000-b996047b0dd7116b667c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niceritrol 40V, Negative-QTOF	splash10-0ktr-5910430000-5af2884331dfd3db76aa	2016-08-03	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

DB13441

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Niceritrol

METLIN ID

Not Available

PubChem Compound

4476

PDB ID

Not Available

ChEBI ID

Not Available

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 Niceritrol (HMDB0255580)

MOL for HMDB0255580 (Niceritrol)

3D MOL for HMDB0255580 (Niceritrol)

3D SDF for HMDB0255580 (Niceritrol)

3D-SDF for HMDB0255580 (Niceritrol)

PDB for HMDB0255580 (Niceritrol)

3D PDB for HMDB0255580 (Niceritrol)

SMILES for HMDB0255580 (Niceritrol)

INCHI for HMDB0255580 (Niceritrol)

Structure for HMDB0255580 (Niceritrol)

3D Structure for HMDB0255580 (Niceritrol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra