MiMeDB: Showing metabocard for Pinolidoxin (MMDBc0013014)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 04:24:57 UTC

Update Date

2022-08-31 06:35:28 UTC

Metabolite ID

MMDBc0013014

Metabolite Identification

Common Name

Pinolidoxin

Description

Pinolidoxin, also known as lethaloxin, belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms. Based on a literature review very few articles have been published on Pinolidoxin.

Structure

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

HMDB0301836
     RDKit          3D
Pinolidoxin
 50 50  0  0  0  0  0  0  0  0999 V2000
    8.1611   -1.6121   -1.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7259   -1.3224   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9024   -1.0534   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -0.7723   -0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6411   -0.5038    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2096   -0.2220    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7389   -0.2324   -1.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3513    0.0571    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    0.3360    0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022    1.7809    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3824    2.7335    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108    3.5587    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8343    3.1542    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097    1.7997   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    1.9736   -1.6200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.9495    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101    1.5677    1.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -0.4497    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -1.0878   -0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -2.4720   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -3.3709    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354   -0.5091    1.6829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -0.5985    1.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -1.4726    2.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -2.6916   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5094   -1.0881   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7716   -1.1940   -2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082   -1.3288   -2.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3065   -1.0451    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0711   -0.7820   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0170   -0.4882    1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2121    0.2700   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928    1.8086    2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    2.1381    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    3.4442    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3223    2.1972   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539    4.5817    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    3.8211    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.4132   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7552    2.3928   -1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776    0.8448    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    2.5355    1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -1.0495    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -0.5176   -1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8913   -1.2926   -1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -2.3853    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006   -2.9207   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -4.3917   -0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8112   -3.5284    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616   -2.9755    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  2  0
 23  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
M  END


  Mrv0541 02241221132D          

 24 24  0  0  0  0            999 V2000
    0.9440    0.1576    0.0000 O   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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.0000    0.0000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    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
    4.2868    2.4750    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0013014

> <DATABASE_NAME>
MIME

> <SMILES>
CCCC1OC(=O)C(CC\C=C\C(O)C1O)OC(=O)\C=C\C=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O6/c1-3-5-6-12-16(20)23-15-11-8-7-10-13(19)17(21)14(9-4-2)24-18(15)22/h3,5-7,10,12-15,17,19,21H,4,8-9,11H2,1-2H3/b5-3+,10-7+,12-6+

> <INCHI_KEY>
TXPRZPDVUZCNLB-YECGNMMBSA-N

> <FORMULA>
C18H26O6

> <MOLECULAR_WEIGHT>
338.3954

> <EXACT_MASS>
338.172938564

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.54133480544297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,9-dihydroxy-2-oxo-10-propyl-3,4,5,8,9,10-hexahydro-2H-oxecin-3-yl (2E,4E)-hexa-2,4-dienoate

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.8737758026666667

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.690566200654704

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.049659722012311

> <JCHEM_PKA_STRONGEST_BASIC>
-3.341324212162853

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
91.82600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pinolidoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301836
     RDKit          3D
Pinolidoxin
 50 50  0  0  0  0  0  0  0  0999 V2000
    8.1611   -1.6121   -1.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7259   -1.3224   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9024   -1.0534   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -0.7723   -0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6411   -0.5038    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2096   -0.2220    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7389   -0.2324   -1.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3513    0.0571    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    0.3360    0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022    1.7809    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3824    2.7335    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108    3.5587    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8343    3.1542    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097    1.7997   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    1.9736   -1.6200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.9495    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101    1.5677    1.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -0.4497    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -1.0878   -0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -2.4720   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -3.3709    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354   -0.5091    1.6829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -0.5985    1.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -1.4726    2.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -2.6916   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5094   -1.0881   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7716   -1.1940   -2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082   -1.3288   -2.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3065   -1.0451    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0711   -0.7820   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0170   -0.4882    1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2121    0.2700   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928    1.8086    2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    2.1381    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    3.4442    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3223    2.1972   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539    4.5817    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    3.8211    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.4132   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7552    2.3928   -1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776    0.8448    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    2.5355    1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -1.0495    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -0.5176   -1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8913   -1.2926   -1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -2.3853    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006   -2.9207   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -4.3917   -0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8112   -3.5284    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616   -2.9755    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  2  0
 23  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.762   0.294   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    4   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0301836
HETATM    1  C1  UNL     1       8.161  -1.612  -1.199  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.726  -1.322  -1.362  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.902  -1.053  -0.366  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.471  -0.772  -0.612  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.641  -0.504   0.366  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.210  -0.222   0.128  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.739  -0.232  -1.043  1.00  0.00           O  
HETATM    8  O2  UNL     1       1.351   0.057   1.153  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.047   0.336   0.961  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.302   1.781   1.382  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.382   2.733   0.237  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.611   3.559   0.390  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.834   3.154   0.082  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.110   1.800  -0.463  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.920   1.974  -1.620  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.805   0.950   0.552  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.910   1.568   1.797  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.190  -0.450   0.703  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.901  -1.088  -0.611  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.306  -2.472  -0.396  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.229  -3.371   0.365  1.00  0.00           C  
HETATM   22  O5  UNL     1      -2.235  -0.509   1.683  1.00  0.00           O  
HETATM   23  C18 UNL     1      -0.899  -0.598   1.735  1.00  0.00           C  
HETATM   24  O6  UNL     1      -0.277  -1.473   2.439  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.381  -2.692  -1.120  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.509  -1.088  -0.278  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.772  -1.194  -2.031  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.308  -1.329  -2.371  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.307  -1.045   0.633  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.071  -0.782  -1.616  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.017  -0.488   1.378  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.212   0.270  -0.111  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.193   1.809   2.042  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.537   2.138   2.047  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.496   3.444   0.218  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.322   2.197  -0.732  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.454   4.582   0.798  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.654   3.821   0.226  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.153   1.413  -0.831  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.755   2.393  -1.285  1.00  0.00           H  
HETATM   41  H17 UNL     1      -4.878   0.845   0.206  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.864   2.536   1.786  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.078  -1.049   1.117  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.257  -0.518  -1.291  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.891  -1.293  -1.114  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.346  -2.385   0.111  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.201  -2.921  -1.415  1.00  0.00           H  
HETATM   48  H24 UNL     1      -3.309  -4.392  -0.094  1.00  0.00           H  
HETATM   49  H25 UNL     1      -2.811  -3.528   1.381  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.262  -2.976   0.463  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   28
CONECT    3    4   29
CONECT    4    5    5   30
CONECT    5    6   31
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   23   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   13   37
CONECT   13   14   38
CONECT   14   15   16   39
CONECT   15   40
CONECT   16   17   18   41
CONECT   17   42
CONECT   18   19   22   43
CONECT   19   20   44   45
CONECT   20   21   46   47
CONECT   21   48   49   50
CONECT   22   23
CONECT   23   24   24
END

HMDB0301836
     RDKit          3D
Pinolidoxin
 50 50  0  0  0  0  0  0  0  0999 V2000
    8.1611   -1.6121   -1.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7259   -1.3224   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9024   -1.0534   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -0.7723   -0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6411   -0.5038    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2096   -0.2220    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7389   -0.2324   -1.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3513    0.0571    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    0.3360    0.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022    1.7809    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3824    2.7335    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108    3.5587    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8343    3.1542    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097    1.7997   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    1.9736   -1.6200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8045    0.9495    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101    1.5677    1.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -0.4497    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -1.0878   -0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -2.4720   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -3.3709    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354   -0.5091    1.6829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -0.5985    1.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -1.4726    2.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3813   -2.6916   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5094   -1.0881   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7716   -1.1940   -2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082   -1.3288   -2.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3065   -1.0451    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0711   -0.7820   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0170   -0.4882    1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2121    0.2700   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928    1.8086    2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    2.1381    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    3.4442    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3223    2.1972   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539    4.5817    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    3.8211    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.4132   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7552    2.3928   -1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8776    0.8448    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    2.5355    1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -1.0495    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -0.5176   -1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8913   -1.2926   -1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -2.3853    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006   -2.9207   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -4.3917   -0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8112   -3.5284    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616   -2.9755    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  2  0
 23  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
M  END

Synonyms

Value	Source
Lethaloxin	MeSH

Molecular Formula

C₁₈H₂₆O₆

Average Mass

338.3954

Monoisotopic Mass

338.172938564

IUPAC Name

8,9-dihydroxy-2-oxo-10-propyl-3,4,5,8,9,10-hexahydro-2H-oxecin-3-yl (2E,4E)-hexa-2,4-dienoate

Traditional Name

pinolidoxin

CAS Registry Number

Not Available

SMILES

CCCC1OC(=O)C(CC\C=C\C(O)C1O)OC(=O)\C=C\C=C\C

InChI Identifier

InChI=1S/C18H26O6/c1-3-5-6-12-16(20)23-15-11-8-7-10-13(19)17(21)14(9-4-2)24-18(15)22/h3,5-7,10,12-15,17,19,21H,4,8-9,11H2,1-2H3/b5-3+,10-7+,12-6+

InChI Key

TXPRZPDVUZCNLB-YECGNMMBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxocins

Sub Class

Not Available

Direct Parent

Oxocins

Alternative Parents

Substituents

Oxocin
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

oxacycle (CHEBI:8223 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.59 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.87	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.05	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	91.83 m³·mol⁻¹	ChemAxon
Polarizability	36.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002s-7189000000-c381f12faa78bdb5515d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kbb-9041000000-5faf499f57bdc29791e6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9010000000-1382c56cce8710d317ab	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01pc-3796000000-1a01c88da7389aca847e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-6961000000-8a0880501c99bf3210e9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-5900000000-3467fc40c8f1b14b891a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0079000000-90553bc642f12154a41c	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004s-2092000000-3c23831ed490d32e5ad6	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-4d67cda740c97e999d94	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0129000000-a123b357efdc174bc6d9	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-2292000000-24f54c14a4f82d9ca58b	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9550000000-43880ba0afaab62fe8fd	2021-10-21	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant		Pisum sativum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0301836

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281169

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Pinolidoxin (MMDBc0013014)

MOL for #<Metabolite:0x00007f46e106b088>

3D MOL for #<Metabolite:0x00007f46e106b088>

3D SDF for #<Metabolite:0x00007f46e106b088>

3D-SDF for #<Metabolite:0x00007f46e106b088>

PDB for #<Metabolite:0x00007f46e106b088>

3D PDB for #<Metabolite:0x00007f46e106b088>

SMILES for #<Metabolite:0x00007f46e106b088>

INCHI for #<Metabolite:0x00007f46e106b088>

Structure for #<Metabolite:0x00007f46e106b088>

3D Structure for #<Metabolite:0x00007f46e106b088>