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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:55:20 UTC

Update Date

2022-03-07 02:54:40 UTC

HMDB ID

HMDB0035879

Secondary Accession Numbers

HMDB35879

Metabolite Identification

Common Name

Hericenone A

Description

Hericenone A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a significant number of articles have been published on Hericenone A.

Structure

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

HMDB0035879
     RDKit          3D
Hericenone A
 46 47  0  0  0  0  0  0  0  0999 V2000
   -2.1711   -2.8671   -1.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -1.8555   -0.3229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721   -0.7317   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -0.5924   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390    0.5075   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2664    1.4811   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847    1.3452    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0278    2.4035    1.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3709    0.2351    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.1384    1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0648    0.4541    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554   -0.3942    1.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -1.6414    1.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353   -0.2756    0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321    0.8743   -0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0050    1.8363   -0.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    1.0460   -0.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1695    0.2763   -0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4142    0.7779   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3141   -1.0446   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2868    2.5530   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1161    2.1129   -1.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7077    0.8891   -1.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2759    0.2591   -2.7965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431   -3.7681   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1285   -2.4741   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322   -3.2207   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9721   -1.3559   -1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212    2.4845    2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    0.8268    2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735   -0.8748    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1388    1.3943    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -2.2012    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287   -2.3040    1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -1.3396    2.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645   -0.2606    1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329   -1.2462    0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650    2.0142   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1426    1.4703   -2.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0644    1.2158   -0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9676   -0.0796   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7506   -1.8600   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3932   -1.4166   -0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589   -0.9821    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7992    3.5192   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8084    2.6711    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
M  END


  Mrv0541 05061308462D          

 24 25  0  0  0  0            999 V2000
    3.3523   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
 18 16  2  0  0  0  0
 19 15  1  0  0  0  0
 20 13  2  0  0  0  0
 21 18  1  0  0  0  0
 22 19  2  0  0  0  0
 23  4  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035879

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O5/c1-11(2)7-13(20)8-12(3)5-6-14-17(23-4)9-15-16(18(14)21)10-24-19(15)22/h5,7,9,21H,6,8,10H2,1-4H3/b12-5+

> <INCHI_KEY>
IDSCVDJWBRGNKG-LFYBBSHMSA-N

> <FORMULA>
C19H22O5

> <MOLECULAR_WEIGHT>
330.375

> <EXACT_MASS>
330.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.89210281439617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.6355221893333334

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.368428725274441

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.004235309674947

> <JCHEM_PKA_STRONGEST_BASIC>
-4.307900945664196

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
93.74549999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-3H-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035879
     RDKit          3D
Hericenone A
 46 47  0  0  0  0  0  0  0  0999 V2000
   -2.1711   -2.8671   -1.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -1.8555   -0.3229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721   -0.7317   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -0.5924   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390    0.5075   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2664    1.4811   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847    1.3452    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0278    2.4035    1.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3709    0.2351    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.1384    1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0648    0.4541    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554   -0.3942    1.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -1.6414    1.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353   -0.2756    0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321    0.8743   -0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0050    1.8363   -0.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    1.0460   -0.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1695    0.2763   -0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4142    0.7779   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3141   -1.0446   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2868    2.5530   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1161    2.1129   -1.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7077    0.8891   -1.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2759    0.2591   -2.7965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431   -3.7681   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1285   -2.4741   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322   -3.2207   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9721   -1.3559   -1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212    2.4845    2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    0.8268    2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735   -0.8748    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1388    1.3943    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -2.2012    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287   -2.3040    1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -1.3396    2.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645   -0.2606    1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329   -1.2462    0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650    2.0142   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1426    1.4703   -2.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0644    1.2158   -0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9676   -0.0796   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7506   -1.8600   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3932   -1.4166   -0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589   -0.9821    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7992    3.5192   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8084    2.6711    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  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       6.258 -11.313   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   23                                                            
CONECT    5    6   12                                                       
CONECT    6    5   14                                                       
CONECT    7   11   13                                                       
CONECT    8   12   13                                                       
CONECT    9   15   17                                                       
CONECT   10   16   24                                                       
CONECT   11    1    2    7                                                  
CONECT   12    3    5    8                                                  
CONECT   13    7    8   20                                                  
CONECT   14    6   17   18                                                  
CONECT   15    9   16   19                                                  
CONECT   16   10   15   18                                                  
CONECT   17    9   14   23                                                  
CONECT   18   14   16   21                                                  
CONECT   19   15   22   24                                                  
CONECT   20   13                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23    4   17                                                       
CONECT   24   10   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0035879
HETATM    1  C1  UNL     1      -2.171  -2.867  -1.273  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.894  -1.855  -0.323  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.672  -0.732  -0.245  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.746  -0.592  -1.117  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.539   0.508  -1.070  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.266   1.481  -0.151  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.185   1.345   0.729  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.028   2.403   1.600  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.371   0.235   0.695  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.248   0.138   1.632  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.065   0.454   1.031  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.055  -0.394   1.156  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.763  -1.641   1.919  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.435  -0.276   0.632  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.832   0.874  -0.122  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.005   1.836  -0.312  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.136   1.046  -0.707  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.169   0.276  -0.699  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.414   0.778  -1.432  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.314  -1.045  -0.076  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.287   2.553  -0.337  1.00  0.00           C  
HETATM   22  O4  UNL     1      -6.116   2.113  -1.368  1.00  0.00           O  
HETATM   23  C19 UNL     1      -5.708   0.889  -1.851  1.00  0.00           C  
HETATM   24  O5  UNL     1      -6.276   0.259  -2.797  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.543  -3.768  -1.114  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.128  -2.474  -2.305  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.232  -3.221  -1.129  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.972  -1.356  -1.848  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.321   2.484   2.280  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.407   0.827   2.468  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.273  -0.875   2.103  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.139   1.394   0.506  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.717  -2.201   2.054  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.029  -2.304   1.507  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.478  -1.340   2.956  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.065  -0.261   1.594  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.633  -1.246   0.106  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.265   2.014  -1.259  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.143   1.470  -2.237  1.00  0.00           H  
HETATM   40  H16 UNL     1       7.064   1.216  -0.648  1.00  0.00           H  
HETATM   41  H17 UNL     1       6.968  -0.080  -1.865  1.00  0.00           H  
HETATM   42  H18 UNL     1       4.751  -1.860  -0.588  1.00  0.00           H  
HETATM   43  H19 UNL     1       6.393  -1.417  -0.161  1.00  0.00           H  
HETATM   44  H20 UNL     1       5.159  -0.982   1.008  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.799   3.519  -0.587  1.00  0.00           H  
HETATM   46  H22 UNL     1      -5.808   2.671   0.646  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   28
CONECT    5    6    6   23
CONECT    6    7   21
CONECT    7    8    9    9
CONECT    8   29
CONECT    9   10
CONECT   10   11   30   31
CONECT   11   12   12   32
CONECT   12   13   14
CONECT   13   33   34   35
CONECT   14   15   36   37
CONECT   15   16   16   17
CONECT   17   18   18   38
CONECT   18   19   20
CONECT   19   39   40   41
CONECT   20   42   43   44
CONECT   21   22   45   46
CONECT   22   23
CONECT   23   24   24
END

HMDB0035879
     RDKit          3D
Hericenone A
 46 47  0  0  0  0  0  0  0  0999 V2000
   -2.1711   -2.8671   -1.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -1.8555   -0.3229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6721   -0.7317   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -0.5924   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390    0.5075   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2664    1.4811   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847    1.3452    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0278    2.4035    1.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3709    0.2351    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.1384    1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0648    0.4541    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554   -0.3942    1.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -1.6414    1.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353   -0.2756    0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321    0.8743   -0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0050    1.8363   -0.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    1.0460   -0.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1695    0.2763   -0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4142    0.7779   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3141   -1.0446   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2868    2.5530   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1161    2.1129   -1.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7077    0.8891   -1.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2759    0.2591   -2.7965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5431   -3.7681   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1285   -2.4741   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322   -3.2207   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9721   -1.3559   -1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212    2.4845    2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    0.8268    2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2735   -0.8748    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1388    1.3943    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -2.2012    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287   -2.3040    1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -1.3396    2.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645   -0.2606    1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329   -1.2462    0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2650    2.0142   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1426    1.4703   -2.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0644    1.2158   -0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9676   -0.0796   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7506   -1.8600   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3932   -1.4166   -0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589   -0.9821    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7992    3.5192   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8084    2.6711    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hericenone a	MeSH

Chemical Formula

C₁₉H₂₂O₅

Average Molecular Weight

330.375

Monoisotopic Molecular Weight

330.146723814

IUPAC Name

5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-1,3-dihydro-2-benzofuran-1-one

Traditional Name

5-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-4-hydroxy-6-methoxy-3H-2-benzofuran-1-one

CAS Registry Number

126654-52-2

SMILES

COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1

InChI Identifier

InChI=1S/C19H22O5/c1-11(2)7-13(20)8-12(3)5-6-14-17(23-4)9-15-16(18(14)21)10-24-19(15)22/h5,7,9,21H,6,8,10H2,1-4H3/b12-5+

InChI Key

IDSCVDJWBRGNKG-LFYBBSHMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Monoterpenoid
Isobenzofuranone
Aromatic monoterpenoid
Bicyclic monoterpenoid
Phthalide
Isocoumaran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Lactone
Carboxylic acid ester
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	100 - 102 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15.85 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	0.012 g/L	ALOGPS
logP	2.74	ALOGPS
logP	3.64	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	93.75 m³·mol⁻¹	ChemAxon
Polarizability	34.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	186.414	30932474
DeepCCS	[M-H]-	183.992	30932474
DeepCCS	[M-2H]-	218.348	30932474
DeepCCS	[M+Na]+	194.43	30932474
AllCCS	[M+H]+	179.8	32859911
AllCCS	[M+H-H2O]+	176.6	32859911
AllCCS	[M+NH4]+	182.7	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	183.2	32859911
AllCCS	[M+Na-2H]-	183.4	32859911
AllCCS	[M+HCOO]-	183.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hericenone A	COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1	4069.7	Standard polar	33892256
Hericenone A	COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1	2680.7	Standard non polar	33892256
Hericenone A	COC1=C(C\C=C(/C)CC(=O)C=C(C)C)C(O)=C2COC(=O)C2=C1	2853.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hericenone A,1TMS,isomer #1	COC1=CC2=C(COC2=O)C(O[Si](C)(C)C)=C1C/C=C(\C)CC(=O)C=C(C)C	2763.9	Semi standard non polar	33892256
Hericenone A,1TMS,isomer #2	COC1=CC2=C(COC2=O)C(O)=C1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C	2935.0	Semi standard non polar	33892256
Hericenone A,2TMS,isomer #1	COC1=CC2=C(COC2=O)C(O[Si](C)(C)C)=C1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C	2942.4	Semi standard non polar	33892256
Hericenone A,2TMS,isomer #1	COC1=CC2=C(COC2=O)C(O[Si](C)(C)C)=C1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C	2834.5	Standard non polar	33892256
Hericenone A,1TBDMS,isomer #1	COC1=CC2=C(COC2=O)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)CC(=O)C=C(C)C	2976.3	Semi standard non polar	33892256
Hericenone A,1TBDMS,isomer #2	COC1=CC2=C(COC2=O)C(O)=C1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	3150.9	Semi standard non polar	33892256
Hericenone A,2TBDMS,isomer #1	COC1=CC2=C(COC2=O)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	3367.0	Semi standard non polar	33892256
Hericenone A,2TBDMS,isomer #1	COC1=CC2=C(COC2=O)C(O[Si](C)(C)C(C)(C)C)=C1C/C=C(\C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	3289.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hericenone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9074000000-89678e16a4f658ad229f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hericenone A GC-MS (1 TMS) - 70eV, Positive	splash10-05ar-7029000000-07604dd019974418cf70	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hericenone A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hericenone A 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 - Hericenone A 10V, Positive-QTOF	splash10-001i-0139000000-21cb5d27fbebc66062bc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 20V, Positive-QTOF	splash10-001l-6493000000-8c2348423b62e99b87b9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 40V, Positive-QTOF	splash10-015c-9540000000-9055ac9077964e7274f2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 10V, Negative-QTOF	splash10-004i-1029000000-1d7d6c94b46b7d7a1794	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 20V, Negative-QTOF	splash10-0a71-6195000000-c7b580d0aeeeb75879ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 40V, Negative-QTOF	splash10-0a4i-9160000000-41ade6321dd057612c91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 10V, Positive-QTOF	splash10-001i-0294000000-ee7ac9ad58d31a3709b4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 20V, Positive-QTOF	splash10-000x-0791000000-b2151931797e34765896	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 40V, Positive-QTOF	splash10-0a6r-5690000000-fc566ee4c85ccab03949	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 10V, Negative-QTOF	splash10-004i-0009000000-a000b3a7619be1462985	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 20V, Negative-QTOF	splash10-00mk-1193000000-f1f18c30b6878440e971	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hericenone A 40V, Negative-QTOF	splash10-016u-5392000000-24301ff5397b0203c582	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB014660

KNApSAcK ID

C00023975

Chemspider ID

9957159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11782478

PDB ID

Not Available

ChEBI ID

175220

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1852261

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 Hericenone A (HMDB0035879)

MOL for HMDB0035879 (Hericenone A)

3D MOL for HMDB0035879 (Hericenone A)

3D SDF for HMDB0035879 (Hericenone A)

3D-SDF for HMDB0035879 (Hericenone A)

PDB for HMDB0035879 (Hericenone A)

3D PDB for HMDB0035879 (Hericenone A)

SMILES for HMDB0035879 (Hericenone A)

INCHI for HMDB0035879 (Hericenone A)

Structure for HMDB0035879 (Hericenone A)

3D Structure for HMDB0035879 (Hericenone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra