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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:58:05 UTC

Update Date

2022-03-07 02:54:20 UTC

HMDB ID

HMDB0035029

Secondary Accession Numbers

HMDB35029

Metabolite Identification

Common Name

Dehydrocyanaropicrin

Description

Dehydrocyanaropicrin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on Dehydrocyanaropicrin.

Structure

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

HMDB0035029
     RDKit          3D
Dehydrocyanaropicrin
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.5093    0.1027    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -0.1672   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2477   -0.2758   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4817   -0.0570   -0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818   -0.3485   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4373   -0.6114   -2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -0.2549    0.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855   -0.4341   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -1.5776    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1259   -1.1976    1.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911   -1.3778    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4635   -0.6510    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5545   -1.7023    1.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6278   -1.0404    0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8572   -1.3159    0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    0.0360   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6878    0.9490   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.1779   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071    0.9940   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573    1.4275   -1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6406    1.7826   -2.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.0285   -3.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2962    1.8259   -1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028    2.5325   -0.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.8691    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666    0.1908    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422    0.2504    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1166    0.5301   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459   -1.2423   -2.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5195    0.8985   -0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676   -0.6479   -1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -2.3076   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -2.1533    1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962   -1.7848    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4786   -1.1296    3.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476    0.1626    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558   -2.6013    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -1.9056    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7705    0.9765   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522    1.7010   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580   -1.0311   -0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    1.8463    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7261    3.1859   -1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9740    2.4383    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    1.2646    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  3
 23 25  1  0
 25  8  1  0
 18 12  1  0
 25 19  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
M  END

  Mrv1652310041912582D          

 25 27  0  0  0  0            999 V2000
    1.1706   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -0.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0653   -0.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -0.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9534   -1.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972   -1.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200   -2.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373    2.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600    1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0571    1.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947    0.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197    0.5644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307    1.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1225    1.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6054    0.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    1.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -0.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620   -0.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    1.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709    1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054    1.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  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
 13 14  2  0  0  0  0
 13 23  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035029

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC(=C)C(=O)OC1CC(=C)C2CC(=O)C(=C)C2C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12,14-17,20H,1-7H2

> <INCHI_KEY>
MSTZNVVCBOEAGA-UHFFFAOYSA-N

> <FORMULA>
C19H20O6

> <MOLECULAR_WEIGHT>
344.3585

> <EXACT_MASS>
344.125988372

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.288213702085336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,9-trimethylidene-2,8-dioxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
1.6083411393333333

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.896380722469186

> <JCHEM_PKA_STRONGEST_BASIC>
-2.844123071991972

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
88.16629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,9-trimethylidene-2,8-dioxo-hexahydro-3aH-azuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035029
     RDKit          3D
Dehydrocyanaropicrin
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.5093    0.1027    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -0.1672   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2477   -0.2758   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4817   -0.0570   -0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818   -0.3485   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4373   -0.6114   -2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -0.2549    0.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855   -0.4341   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -1.5776    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1259   -1.1976    1.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911   -1.3778    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4635   -0.6510    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5545   -1.7023    1.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6278   -1.0404    0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8572   -1.3159    0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    0.0360   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6878    0.9490   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.1779   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071    0.9940   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573    1.4275   -1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6406    1.7826   -2.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.0285   -3.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2962    1.8259   -1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028    2.5325   -0.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.8691    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666    0.1908    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422    0.2504    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1166    0.5301   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459   -1.2423   -2.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5195    0.8985   -0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676   -0.6479   -1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -2.3076   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -2.1533    1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962   -1.7848    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4786   -1.1296    3.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476    0.1626    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558   -2.6013    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -1.9056    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7705    0.9765   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522    1.7010   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580   -1.0311   -0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    1.8463    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7261    3.1859   -1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9740    2.4383    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    1.2646    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  3
 23 25  1  0
 25  8  1  0
 18 12  1  0
 25 19  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 04-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-19         0                                  
HETATM    1  C   UNK     0       2.185  -1.800   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.648  -1.654   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.122  -0.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.631  -0.656   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.780  -2.188   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.368  -2.804   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.037  -4.307   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.936   4.307   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.605   2.803   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.106   2.452   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.550   1.054   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.090   1.054   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.857   2.383   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.095   3.704   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -6.730   1.107   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.190   1.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.277   2.339   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.822   1.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.822   0.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.295  -0.150   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.782  -1.613   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.188   1.035   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.410   2.383   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.172   3.702   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.730   3.702   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11    3   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18    9   17   19                                                  
CONECT   19    4   18   20                                                  
CONECT   20   16   19   21                                                  
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   13   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0035029
HETATM    1  C1  UNL     1       4.509   0.103   0.767  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.189  -0.167  -0.482  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.248  -0.276  -1.492  1.00  0.00           C  
HETATM    4  O1  UNL     1       6.482  -0.057  -0.896  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.782  -0.348  -0.811  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.437  -0.611  -2.014  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.766  -0.255   0.103  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.385  -0.434  -0.227  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.095  -1.578   0.613  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.126  -1.198   1.597  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.791  -1.378   2.870  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.463  -0.651   1.378  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.554  -1.702   1.400  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.628  -1.040   0.610  1.00  0.00           C  
HETATM   15  O4  UNL     1      -5.857  -1.316   0.594  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.994   0.036  -0.186  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.688   0.949  -0.833  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.565  -0.178  -0.061  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.707   0.994  -0.270  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.857   1.428  -1.619  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.641   1.783  -2.131  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.362   2.028  -3.330  1.00  0.00           O  
HETATM   23  C17 UNL     1       0.296   1.826  -1.010  1.00  0.00           C  
HETATM   24  C18 UNL     1       1.403   2.533  -0.890  1.00  0.00           C  
HETATM   25  C19 UNL     1      -0.277   0.869   0.009  1.00  0.00           C  
HETATM   26  H1  UNL     1       3.767   0.191   1.537  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.542   0.250   1.084  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.117   0.530  -2.269  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.246  -1.242  -2.034  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.520   0.899  -0.639  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.368  -0.648  -1.317  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.587  -2.308  -0.096  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.721  -2.153   1.096  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.196  -1.785   3.134  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.479  -1.130   3.674  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.648   0.163   2.106  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.156  -2.601   0.876  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.939  -1.906   2.402  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.771   0.977  -0.830  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.152   1.701  -1.390  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.258  -1.031  -0.700  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.119   1.846   0.348  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.726   3.186  -1.676  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.974   2.438   0.014  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.041   1.265   0.994  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3    5
CONECT    3    4   28   29
CONECT    4   30
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   25   31
CONECT    9   10   32   33
CONECT   10   11   11   12
CONECT   11   34   35
CONECT   12   13   18   36
CONECT   13   14   37   38
CONECT   14   15   15   16
CONECT   16   17   17   18
CONECT   17   39   40
CONECT   18   19   41
CONECT   19   20   25   42
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   24   25
CONECT   24   43   44
CONECT   25   45
END

HMDB0035029
     RDKit          3D
Dehydrocyanaropicrin
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.5093    0.1027    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -0.1672   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2477   -0.2758   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4817   -0.0570   -0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818   -0.3485   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4373   -0.6114   -2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -0.2549    0.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855   -0.4341   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -1.5776    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1259   -1.1976    1.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911   -1.3778    2.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4635   -0.6510    1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5545   -1.7023    1.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6278   -1.0404    0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8572   -1.3159    0.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    0.0360   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6878    0.9490   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.1779   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071    0.9940   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573    1.4275   -1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6406    1.7826   -2.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.0285   -3.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2962    1.8259   -1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028    2.5325   -0.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.8691    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666    0.1908    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422    0.2504    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1166    0.5301   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459   -1.2423   -2.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5195    0.8985   -0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676   -0.6479   -1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -2.3076   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -2.1533    1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1962   -1.7848    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4786   -1.1296    3.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476    0.1626    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558   -2.6013    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -1.9056    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7705    0.9765   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522    1.7010   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580   -1.0311   -0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    1.8463    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7261    3.1859   -1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9740    2.4383    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    1.2646    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  3
 23 25  1  0
 25  8  1  0
 18 12  1  0
 25 19  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,6,9-Trimethylidene-2,8-dioxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoic acid	HMDB

Chemical Formula

C₁₉H₂₀O₆

Average Molecular Weight

344.3585

Monoisotopic Molecular Weight

344.125988372

IUPAC Name

3,6,9-trimethylidene-2,8-dioxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

Traditional Name

3,6,9-trimethylidene-2,8-dioxo-hexahydro-3aH-azuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

CAS Registry Number

35821-02-4

SMILES

OCC(=C)C(=O)OC1CC(=C)C2CC(=O)C(=C)C2C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C19H20O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12,14-17,20H,1-7H2

InChI Key

MSTZNVVCBOEAGA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035029)

Source

Endogenous

Endogenous (HMDB: HMDB0035029)

Plant

Plant (HMDB: HMDB0035029)

Animal

Animal (HMDB: HMDB0035029)

Exogenous

Food

Food (HMDB: HMDB0035029)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0035029)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035029)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035029)

Lipid metabolism pathway (HMDB: HMDB0035029)

Cellular process

Cell signaling (HMDB: HMDB0035029)

Biochemical process

Lipid transport (HMDB: HMDB0035029)

Role

Biological role

Energy source (HMDB: HMDB0035029)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035029)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	126 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4533 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	0.86	ALOGPS
logP	1.61	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.9	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.17 m³·mol⁻¹	ChemAxon
Polarizability	34.29 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	180.595	31661259
DarkChem	[M-H]-	175.957	31661259
DeepCCS	[M-2H]-	213.45	30932474
DeepCCS	[M+Na]+	188.996	30932474
AllCCS	[M+H]+	180.2	32859911
AllCCS	[M+H-H2O]+	177.3	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.5	32859911
AllCCS	[M-H]-	181.1	32859911
AllCCS	[M+Na-2H]-	181.0	32859911
AllCCS	[M+HCOO]-	181.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrocyanaropicrin	OCC(=C)C(=O)OC1CC(=C)C2CC(=O)C(=C)C2C2OC(=O)C(=C)C12	3787.8	Standard polar	33892256
Dehydrocyanaropicrin	OCC(=C)C(=O)OC1CC(=C)C2CC(=O)C(=C)C2C2OC(=O)C(=C)C12	2636.5	Standard non polar	33892256
Dehydrocyanaropicrin	OCC(=C)C(=O)OC1CC(=C)C2CC(=O)C(=C)C2C2OC(=O)C(=C)C12	2903.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydrocyanaropicrin,1TMS,isomer #1	C=C(CO[Si](C)(C)C)C(=O)OC1CC(=C)C2CC(=O)C(=C)C2C2OC(=O)C(=C)C12	2734.3	Semi standard non polar	33892256
Dehydrocyanaropicrin,1TMS,isomer #2	C=C(CO)C(=O)OC1CC(=C)C2C=C(O[Si](C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2707.1	Semi standard non polar	33892256
Dehydrocyanaropicrin,2TMS,isomer #1	C=C(CO[Si](C)(C)C)C(=O)OC1CC(=C)C2C=C(O[Si](C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2749.9	Semi standard non polar	33892256
Dehydrocyanaropicrin,2TMS,isomer #1	C=C(CO[Si](C)(C)C)C(=O)OC1CC(=C)C2C=C(O[Si](C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2549.6	Standard non polar	33892256
Dehydrocyanaropicrin,1TBDMS,isomer #1	C=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC1CC(=C)C2CC(=O)C(=C)C2C2OC(=O)C(=C)C12	2929.5	Semi standard non polar	33892256
Dehydrocyanaropicrin,1TBDMS,isomer #2	C=C(CO)C(=O)OC1CC(=C)C2C=C(O[Si](C)(C)C(C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2907.8	Semi standard non polar	33892256
Dehydrocyanaropicrin,2TBDMS,isomer #1	C=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC1CC(=C)C2C=C(O[Si](C)(C)C(C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	3155.1	Semi standard non polar	33892256
Dehydrocyanaropicrin,2TBDMS,isomer #1	C=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC1CC(=C)C2C=C(O[Si](C)(C)C(C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2889.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrocyanaropicrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-9262000000-c161894f03af44dfbf30	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrocyanaropicrin GC-MS (1 TMS) - 70eV, Positive	splash10-0a6u-9328000000-1d9bc4bca9ed5d092234	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrocyanaropicrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Dehydrocyanaropicrin 10V, Positive-QTOF	splash10-004j-2049000000-442e2f23bd70c3a6182d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 20V, Positive-QTOF	splash10-052r-7495000000-ba0b22c1f38f1c77ffa8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 40V, Positive-QTOF	splash10-000i-9300000000-91f04550acb50684b12c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 10V, Negative-QTOF	splash10-0006-0049000000-78b8ce779464f13dee29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 20V, Negative-QTOF	splash10-0a4l-7189000000-d50c38b3c0622f95c495	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 40V, Negative-QTOF	splash10-0zir-6920000000-1e42c4d143e79a83c807	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 10V, Negative-QTOF	splash10-0006-3091000000-9d72f6ebf0efa724c46b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 20V, Negative-QTOF	splash10-014i-9010000000-ff99618622b62f32b1fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 40V, Negative-QTOF	splash10-0a4r-5490000000-1277e8d39fdf74413e5b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 10V, Positive-QTOF	splash10-0006-0090000000-158254bb1063055de98f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 20V, Positive-QTOF	splash10-0006-0191000000-7bac97b8c7529ee42818	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocyanaropicrin 40V, Positive-QTOF	splash10-00ri-3970000000-b70317fe01f3b3e0b2c9	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB013635

KNApSAcK ID

C00020513

Chemspider ID

35013817

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71437252

PDB ID

Not Available

ChEBI ID

168970

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1846991

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Dehydrocyanaropicrin (HMDB0035029)

MOL for HMDB0035029 (Dehydrocyanaropicrin)

3D MOL for HMDB0035029 (Dehydrocyanaropicrin)

3D SDF for HMDB0035029 (Dehydrocyanaropicrin)

3D-SDF for HMDB0035029 (Dehydrocyanaropicrin)

PDB for HMDB0035029 (Dehydrocyanaropicrin)

3D PDB for HMDB0035029 (Dehydrocyanaropicrin)

SMILES for HMDB0035029 (Dehydrocyanaropicrin)

INCHI for HMDB0035029 (Dehydrocyanaropicrin)

Structure for HMDB0035029 (Dehydrocyanaropicrin)

3D Structure for HMDB0035029 (Dehydrocyanaropicrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra