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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:33:39 UTC

Update Date

2022-03-07 02:54:55 UTC

HMDB ID

HMDB0036423

Secondary Accession Numbers

HMDB36423

Metabolite Identification

Common Name

Cynaropicrin

Description

Cynaropicrin 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 significant number of articles have been published on Cynaropicrin.

Structure

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

HMDB0036423
     RDKit          3D
Cynaropicrin
 47 49  0  0  0  0  0  0  0  0999 V2000
    3.2692    1.8324    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.8822    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3210    0.8373    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967    1.9226    0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -0.1496   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -1.0972   -0.8366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520   -0.1480    0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -1.1387   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1236   -1.9311    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929   -1.3921    1.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -2.3155    1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -0.0219    1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9378    0.0373    1.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995    1.3997    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    2.3577    2.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    1.7134    0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6860    2.6836   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.7622    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -0.0209   -1.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339   -1.1913   -0.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938   -1.9367   -2.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -2.8537   -2.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4696   -1.4815   -2.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058   -1.8626   -3.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0565   -0.4850   -1.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    2.5966    1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2095    1.8691    1.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799   -0.1349    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4835    0.8708   -0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2702    2.5179    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -1.8373   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221   -2.1950    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718   -2.9630    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -3.3659    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -2.0569    2.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    0.4908    2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5226   -0.7211    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -0.0410    2.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508    1.3270    1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    2.7087    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832    2.8670   -1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.3348   -0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.3694    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228    0.6241   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1709   -1.4176   -3.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555   -2.5987   -4.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783    0.3529   -2.0410 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  1  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
 14 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
M  END


  Mrv0541 05061309082D          

 25 27  0  0  0  0            999 V2000
   -1.6655   -2.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3633   -0.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -3.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5911   -0.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -1.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6018   -3.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778    0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3633   -0.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7331   -3.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172   -0.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -2.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656   -4.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656   -0.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -2.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8089   -1.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -1.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922   -0.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656   -4.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    1.1330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9428   -1.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656   -0.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142   -2.1657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  2  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20  7  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  2  0  0  0  0
 23 19  2  0  0  0  0
 24 14  1  0  0  0  0
 24 18  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036423

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O6/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/h12-17,20-21H,1-7H2

> <INCHI_KEY>
KHSCYOFDKADJDJ-UHFFFAOYSA-N

> <FORMULA>
C19H22O6

> <MOLECULAR_WEIGHT>
346.3744

> <EXACT_MASS>
346.141638436

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.055579406302485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
1.0448134336666668

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.425167201280306

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.627313135923267

> <JCHEM_PKA_STRONGEST_BASIC>
-2.844123071929464

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
88.98859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
saupirin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036423
     RDKit          3D
Cynaropicrin
 47 49  0  0  0  0  0  0  0  0999 V2000
    3.2692    1.8324    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.8822    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3210    0.8373    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967    1.9226    0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -0.1496   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -1.0972   -0.8366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520   -0.1480    0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -1.1387   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1236   -1.9311    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929   -1.3921    1.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -2.3155    1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -0.0219    1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9378    0.0373    1.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995    1.3997    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    2.3577    2.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    1.7134    0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6860    2.6836   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.7622    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -0.0209   -1.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339   -1.1913   -0.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938   -1.9367   -2.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -2.8537   -2.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4696   -1.4815   -2.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058   -1.8626   -3.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0565   -0.4850   -1.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    2.5966    1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2095    1.8691    1.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799   -0.1349    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4835    0.8708   -0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2702    2.5179    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -1.8373   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221   -2.1950    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718   -2.9630    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -3.3659    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -2.0569    2.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    0.4908    2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5226   -0.7211    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -0.0410    2.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508    1.3270    1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    2.7087    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832    2.8670   -1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.3348   -0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.3694    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228    0.6241   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1709   -1.4176   -3.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555   -2.5987   -4.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783    0.3529   -2.0410 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  1  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
 14 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -3.109  -4.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.545  -1.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.833  -7.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.970  -0.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.265  -2.403   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.123  -6.573   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.879   0.575   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.608  -3.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.545  -0.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.368  -6.573   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.832  -1.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.648  -5.109   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.122  -7.478   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.122  -1.735   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.892  -5.109   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.510  -2.403   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.853  -3.905   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.211   0.575   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.992  -2.627   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.212  -0.195   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.122  -9.018   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.211   2.115   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.493  -2.284   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.122  -0.195   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.387  -4.043   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5    8   14                                                       
CONECT    6   12   13                                                       
CONECT    7    9   20                                                       
CONECT    8    1    5   12                                                  
CONECT    9    2    7   18                                                  
CONECT   10    3   13   15                                                  
CONECT   11    4   16   19                                                  
CONECT   12    6    8   15                                                  
CONECT   13    6   10   21                                                  
CONECT   14    5   16   24                                                  
CONECT   15   10   12   17                                                  
CONECT   16   11   14   17                                                  
CONECT   17   15   16   25                                                  
CONECT   18    9   22   24                                                  
CONECT   19   11   23   25                                                  
CONECT   20    7                                                            
CONECT   21   13                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   14   18                                                       
CONECT   25   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0036423
HETATM    1  C1  UNL     1       3.269   1.832   1.130  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.855   0.882   0.433  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.321   0.837   0.226  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.897   1.923   0.873  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.029  -0.150  -0.149  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.545  -1.097  -0.837  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.652  -0.148   0.018  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.800  -1.139  -0.533  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.124  -1.931   0.504  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.993  -1.392   1.238  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.740  -2.315   1.837  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.459  -0.022   1.464  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.938   0.037   1.822  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.400   1.400   1.330  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.349   2.358   2.337  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.486   1.713   0.199  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.686   2.684  -0.665  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.323   0.762   0.204  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.389  -0.021  -1.059  1.00  0.00           C  
HETATM   20  O5  UNL     1      -2.134  -1.191  -0.990  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.794  -1.937  -2.111  1.00  0.00           C  
HETATM   22  O6  UNL     1      -2.447  -2.854  -2.690  1.00  0.00           O  
HETATM   23  C17 UNL     1      -0.470  -1.481  -2.567  1.00  0.00           C  
HETATM   24  C18 UNL     1       0.206  -1.863  -3.627  1.00  0.00           C  
HETATM   25  C19 UNL     1      -0.056  -0.485  -1.555  1.00  0.00           C  
HETATM   26  H1  UNL     1       3.902   2.597   1.558  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.209   1.869   1.283  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.680  -0.135   0.594  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.484   0.871  -0.880  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.270   2.518   0.155  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.488  -1.837  -1.077  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.922  -2.195   1.270  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.172  -2.963   0.128  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.501  -3.366   1.759  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.594  -2.057   2.419  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.926   0.491   2.302  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.523  -0.721   1.265  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.121  -0.041   2.902  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.451   1.327   1.001  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.432   2.709   2.392  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.983   2.867  -1.473  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.546   3.335  -0.613  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.411   1.369   0.206  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.823   0.624  -1.844  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.171  -1.418  -3.807  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.155  -2.599  -4.329  1.00  0.00           H  
HETATM   47  H22 UNL     1       0.478   0.353  -2.041  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   16   39
CONECT   15   40
CONECT   16   17   17   18
CONECT   17   41   42
CONECT   18   19   43
CONECT   19   20   25   44
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   24   25
CONECT   24   45   46
CONECT   25   47
END

HMDB0036423
     RDKit          3D
Cynaropicrin
 47 49  0  0  0  0  0  0  0  0999 V2000
    3.2692    1.8324    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.8822    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3210    0.8373    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967    1.9226    0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -0.1496   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -1.0972   -0.8366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520   -0.1480    0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -1.1387   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1236   -1.9311    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929   -1.3921    1.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -2.3155    1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -0.0219    1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9378    0.0373    1.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995    1.3997    1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    2.3577    2.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    1.7134    0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6860    2.6836   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.7622    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -0.0209   -1.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339   -1.1913   -0.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938   -1.9367   -2.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -2.8537   -2.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4696   -1.4815   -2.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058   -1.8626   -3.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0565   -0.4850   -1.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    2.5966    1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2095    1.8691    1.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799   -0.1349    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4835    0.8708   -0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2702    2.5179    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -1.8373   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221   -2.1950    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718   -2.9630    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -3.3659    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -2.0569    2.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    0.4908    2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5226   -0.7211    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -0.0410    2.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508    1.3270    1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    2.7087    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832    2.8670   -1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.3348   -0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    1.3694    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228    0.6241   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1709   -1.4176   -3.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1555   -2.5987   -4.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783    0.3529   -2.0410 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  1  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
 14 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₆

Average Molecular Weight

346.3744

Monoisotopic Molecular Weight

346.141638436

IUPAC Name

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

Traditional Name

saupirin

CAS Registry Number

35730-78-0

SMILES

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

InChI Identifier

InChI=1S/C19H22O6/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/h12-17,20-21H,1-7H2

InChI Key

KHSCYOFDKADJDJ-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
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:9042 )
Guaianolide (C09547 )

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Disposition

Biological location

Cell membrane (HMDB: HMDB0036423)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036423)

Source

Endogenous

Endogenous (HMDB: HMDB0036423)

Plant

Plant (HMDB: HMDB0036423)

Animal

Animal (HMDB: HMDB0036423)

Exogenous

Food

Food (HMDB: HMDB0036423)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)
Cardoon (FooDB: FOOD00319)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036423)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036423)

Cellular process

Cell signaling (HMDB: HMDB0036423)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036423)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036423)

Nutrient

Nutrient (HMDB: HMDB0036423)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036423)

Emulsifier (HMDB: HMDB0036423)

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
Water Solubility	1.6 g/L	ALOGPS
logP	0.54	ALOGPS
logP	1.04	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	-2.8	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	4	ChemAxon
Refractivity	88.99 m³·mol⁻¹	ChemAxon
Polarizability	35.06 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]+	181.052	31661259
DarkChem	[M-H]-	175.566	31661259
DeepCCS	[M-2H]-	213.633	30932474
DeepCCS	[M+Na]+	189.54	30932474
AllCCS	[M+H]+	181.8	32859911
AllCCS	[M+H-H2O]+	179.0	32859911
AllCCS	[M+NH4]+	184.4	32859911
AllCCS	[M+Na]+	185.1	32859911
AllCCS	[M-H]-	181.7	32859911
AllCCS	[M+Na-2H]-	181.7	32859911
AllCCS	[M+HCOO]-	181.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cynaropicrin	OCC(=C)C(=O)OC1CC(=C)C2CC(O)C(=C)C2C2OC(=O)C(=C)C12	3804.9	Standard polar	33892256
Cynaropicrin	OCC(=C)C(=O)OC1CC(=C)C2CC(O)C(=C)C2C2OC(=O)C(=C)C12	2640.0	Standard non polar	33892256
Cynaropicrin	OCC(=C)C(=O)OC1CC(=C)C2CC(O)C(=C)C2C2OC(=O)C(=C)C12	2943.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cynaropicrin,1TMS,isomer #1	C=C(CO[Si](C)(C)C)C(=O)OC1CC(=C)C2CC(O)C(=C)C2C2OC(=O)C(=C)C12	2718.3	Semi standard non polar	33892256
Cynaropicrin,1TMS,isomer #2	C=C(CO)C(=O)OC1CC(=C)C2CC(O[Si](C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2705.5	Semi standard non polar	33892256
Cynaropicrin,2TMS,isomer #1	C=C(CO[Si](C)(C)C)C(=O)OC1CC(=C)C2CC(O[Si](C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2754.9	Semi standard non polar	33892256
Cynaropicrin,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	2910.0	Semi standard non polar	33892256
Cynaropicrin,1TBDMS,isomer #2	C=C(CO)C(=O)OC1CC(=C)C2CC(O[Si](C)(C)C(C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	2912.4	Semi standard non polar	33892256
Cynaropicrin,2TBDMS,isomer #1	C=C(CO[Si](C)(C)C(C)(C)C)C(=O)OC1CC(=C)C2CC(O[Si](C)(C)C(C)(C)C)C(=C)C2C2OC(=O)C(=C)C12	3151.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cynaropicrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udj-9187000000-46a8f12766f2f5a77254	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cynaropicrin GC-MS (2 TMS) - 70eV, Positive	splash10-004i-9628800000-2472b7cee48d840fd6b9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cynaropicrin 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 - Cynaropicrin 10V, Positive-QTOF	splash10-004j-1039000000-3013b817a1eb66d4d93c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 20V, Positive-QTOF	splash10-0550-5294000000-180d098e42694860f41e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 40V, Positive-QTOF	splash10-000i-9310000000-d41612fc5e876f7cf9c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 10V, Negative-QTOF	splash10-0002-0029000000-7db22ac9becc0594febe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 20V, Negative-QTOF	splash10-0kbb-6169000000-03993446bf310466f70a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 40V, Negative-QTOF	splash10-0zir-5920000000-88d876f089635eb90e00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 10V, Negative-QTOF	splash10-004i-1091000000-2526c381422e96ac622d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 20V, Negative-QTOF	splash10-014i-9010000000-758adecc98a17d8063b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 40V, Negative-QTOF	splash10-002f-3090000000-5104c6a5d9f4554bd51c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 10V, Positive-QTOF	splash10-0002-0090000000-2b2af4889486b18bdc8a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 20V, Positive-QTOF	splash10-004i-0091000000-2530f80e510decef2036	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaropicrin 40V, Positive-QTOF	splash10-00wa-3490000000-220f0ef58b3f6a99302b	2021-09-24	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cynaropicrin

METLIN ID

Not Available

PubChem Compound

181128

PDB ID

Not Available

ChEBI ID

9042

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

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 Cynaropicrin (HMDB0036423)

MOL for HMDB0036423 (Cynaropicrin)

3D MOL for HMDB0036423 (Cynaropicrin)

3D SDF for HMDB0036423 (Cynaropicrin)

3D-SDF for HMDB0036423 (Cynaropicrin)

PDB for HMDB0036423 (Cynaropicrin)

3D PDB for HMDB0036423 (Cynaropicrin)

SMILES for HMDB0036423 (Cynaropicrin)

INCHI for HMDB0036423 (Cynaropicrin)

Structure for HMDB0036423 (Cynaropicrin)

3D Structure for HMDB0036423 (Cynaropicrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra