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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (2) Show 5 proteins XML

enzymes (3)transporters (2) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:57 UTC

Update Date

2022-03-07 02:52:33 UTC

HMDB ID

HMDB0030463

Secondary Accession Numbers

HMDB30463

Metabolite Identification

Common Name

Hyperforin

Description

Hyperforin is found in alcoholic beverages. Hyperforin is a constituent of Hypericum perforatum (St John's Wort) Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John's wort). The structure of hyperforin was elucidated by a research group from the Shemyakin Institute of Bio-organic Chemistry (USSR Academy of Sciences in Moscow) and published in 1975. Hyperforin is a prenylated phloroglucinol derivative. Total synthesis of hyperforin has not yet been accomplished, despite attempts by several research groups

Structure

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


  Mrv0541 05061305142D          

 39 40  0  0  0  0            999 V2000
    0.0140   -2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531   -2.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209   -1.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514   -1.0806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1585    2.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7244    1.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808    0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    0.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736    1.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9831    2.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173    3.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    0.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7614    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0827    1.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0219    0.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 36  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 33  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
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  9 18  1  0  0  0  0
  9 32  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  2  0  0  0  0
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 33 34  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 38 39  2  0  0  0  0
M  END

HMDB0030463
     RDKit          3D
Hyperforin
 91 92  0  0  0  0  0  0  0  0999 V2000
    4.3680    3.6244   -1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112    3.5576   -2.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4083    0.2195    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.3679    1.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -1.2112    0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4784   -4.3898    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -3.5955    1.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0839   -1.4590   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9798   -0.2022   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1093   -2.5531   -0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061305142D          

 39 40  0  0  0  0            999 V2000
    0.0140   -2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531   -2.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1619   -0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514   -1.0806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3736    1.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3505    2.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0827    1.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453    1.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7406    3.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1487    3.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6449    3.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890   -1.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5955   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -2.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9865   -0.0922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -0.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5123   -0.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2802   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8636   -1.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462   -3.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175   -3.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1708   -0.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    0.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 36  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 33  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
  9 32  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
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 16 38  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 25  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 31  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 33 34  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030463

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3

> <INCHI_KEY>
KGSZHKRKHXOAMG-UHFFFAOYSA-N

> <FORMULA>
C35H52O4

> <MOLECULAR_WEIGHT>
536.785

> <EXACT_MASS>
536.386560152

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
63.573389397195896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

> <ALOGPS_LOGP>
6.32

> <JCHEM_LOGP>
9.666358571

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.34434546630505

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.174655627140079

> <JCHEM_PKA_STRONGEST_BASIC>
-6.221605628699888

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
166.68250000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.97e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030463
     RDKit          3D
Hyperforin
 91 92  0  0  0  0  0  0  0  0999 V2000
    4.3680    3.6244   -1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112    3.5576   -2.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4037    4.1209   -3.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439    3.0298   -1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9198    2.4790   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4083    0.2195    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3831   -1.2112    0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7031   -2.3560    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0079   -2.5347    1.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764   -3.4858    1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784   -4.3898    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0435    1.4601    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703   -1.1878   -0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8944   -2.5833    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5852   -3.3277    0.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3222   -1.9300    2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3454   -5.0594   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489   -5.0447    0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -3.8208   -0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -2.8448    1.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239   -4.6018    1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0942   -3.4003    3.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -0.9218   -1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093   -2.5531   -0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -1.9974    0.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5915   -3.1124    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372   -3.0697   -1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6917   -3.0123    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8365   -3.2459   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158   -1.6113   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
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 37 89  1  0
 37 90  1  0
 39 91  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       0.026  -5.261   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.219  -4.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.972  -2.767   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.169  -1.571   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.643  -2.017   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.163   4.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.352   3.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.081   2.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.271   0.822   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.767   0.523   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.431   3.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.702   4.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.512   6.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.812   1.754   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.369   0.280   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.870  -0.074   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.421   1.571   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.074   2.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.451   3.513   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.654   4.586   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.754   3.583   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.311   2.108   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.367   0.987   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.382   7.152   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.278   6.079   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.204   6.500   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.459  -3.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.978  -2.738   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.873  -3.810   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.708  -0.172   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.603  -1.244   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.956  -0.823   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.523  -2.075   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.612  -3.109   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.920  -7.755   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.273  -6.781   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.713  -7.328   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.319  -0.068   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.041   1.301   0.000  0.00  0.00           O+0
CONECT    1    2   36                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4                                                            
CONECT    6    7   12                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18   32                                             
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    6   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15   22                                                       
CONECT   15   14   16                                                       
CONECT   16    4   15   17   38                                             
CONECT   17   16   18                                                       
CONECT   18    9   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   25                                                       
CONECT   21   22                                                            
CONECT   22   14   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   20   24   26                                                  
CONECT   26   25                                                            
CONECT   27   28                                                            
CONECT   28   27   29   31                                                  
CONECT   29   28                                                            
CONECT   30   31                                                            
CONECT   31   28   30   32                                                  
CONECT   32    9   31   33   38                                             
CONECT   33    3   32   34                                                  
CONECT   34   33                                                            
CONECT   35   36                                                            
CONECT   36    1   35   37                                                  
CONECT   37   36                                                            
CONECT   38   16   32   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

COMPND    HMDB0030463
HETATM    1  C1  UNL     1       4.368   3.624  -1.316  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.211   3.558  -2.243  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.404   4.121  -3.633  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.044   3.030  -1.894  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.920   2.479  -0.476  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.586   1.034  -0.582  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.408   0.220   0.674  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.718   0.368   1.437  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.383  -1.211   0.161  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.703  -2.356   0.988  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.008  -2.535   1.623  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.876  -3.486   1.255  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.478  -4.390   0.152  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.172  -3.596   1.947  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.084  -1.459  -0.654  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.135  -1.109   0.184  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.060  -2.281   0.330  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.594  -2.811  -0.933  1.00  0.00           C  
HETATM   19  C19 UNL     1      -3.854  -3.005  -1.239  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.921  -2.688  -0.274  1.00  0.00           C  
HETATM   21  C21 UNL     1      -4.213  -3.555  -2.595  1.00  0.00           C  
HETATM   22  C22 UNL     1      -0.742  -0.634   1.519  1.00  0.00           C  
HETATM   23  O1  UNL     1      -1.134  -1.118   2.491  1.00  0.00           O  
HETATM   24  C23 UNL     1       0.208   0.534   1.516  1.00  0.00           C  
HETATM   25  C24 UNL     1       0.539   1.032   2.873  1.00  0.00           C  
HETATM   26  O2  UNL     1       1.095   2.159   2.807  1.00  0.00           O  
HETATM   27  C25 UNL     1       0.345   0.477   4.190  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.882  -0.849   4.529  1.00  0.00           C  
HETATM   29  C27 UNL     1      -1.103   0.581   4.700  1.00  0.00           C  
HETATM   30  C28 UNL     1      -0.703   1.585   0.923  1.00  0.00           C  
HETATM   31  O3  UNL     1      -0.813   2.718   1.448  1.00  0.00           O  
HETATM   32  C29 UNL     1      -1.496   1.311  -0.284  1.00  0.00           C  
HETATM   33  C30 UNL     1      -1.841   2.398  -1.237  1.00  0.00           C  
HETATM   34  C31 UNL     1      -2.617   1.994  -2.400  1.00  0.00           C  
HETATM   35  C32 UNL     1      -3.794   2.547  -2.636  1.00  0.00           C  
HETATM   36  C33 UNL     1      -4.576   2.121  -3.831  1.00  0.00           C  
HETATM   37  C34 UNL     1      -4.385   3.590  -1.750  1.00  0.00           C  
HETATM   38  C35 UNL     1      -1.874   0.034  -0.455  1.00  0.00           C  
HETATM   39  O4  UNL     1      -2.980  -0.202  -1.250  1.00  0.00           O  
HETATM   40  H1  UNL     1       5.206   4.125  -1.839  1.00  0.00           H  
HETATM   41  H2  UNL     1       4.738   2.617  -1.026  1.00  0.00           H  
HETATM   42  H3  UNL     1       4.163   4.237  -0.413  1.00  0.00           H  
HETATM   43  H4  UNL     1       3.606   3.336  -4.375  1.00  0.00           H  
HETATM   44  H5  UNL     1       4.253   4.822  -3.635  1.00  0.00           H  
HETATM   45  H6  UNL     1       2.479   4.710  -3.833  1.00  0.00           H  
HETATM   46  H7  UNL     1       1.228   2.996  -2.593  1.00  0.00           H  
HETATM   47  H8  UNL     1       1.197   3.141  -0.018  1.00  0.00           H  
HETATM   48  H9  UNL     1       2.962   2.646  -0.054  1.00  0.00           H  
HETATM   49  H10 UNL     1       0.714   0.970  -1.275  1.00  0.00           H  
HETATM   50  H11 UNL     1       2.423   0.585  -1.215  1.00  0.00           H  
HETATM   51  H12 UNL     1       2.643   0.161   2.502  1.00  0.00           H  
HETATM   52  H13 UNL     1       3.497  -0.211   0.971  1.00  0.00           H  
HETATM   53  H14 UNL     1       3.044   1.460   1.423  1.00  0.00           H  
HETATM   54  H15 UNL     1       2.170  -1.188  -0.691  1.00  0.00           H  
HETATM   55  H16 UNL     1       0.894  -2.583   1.762  1.00  0.00           H  
HETATM   56  H17 UNL     1       1.585  -3.328   0.349  1.00  0.00           H  
HETATM   57  H18 UNL     1       3.322  -1.930   2.456  1.00  0.00           H  
HETATM   58  H19 UNL     1       4.345  -5.059  -0.047  1.00  0.00           H  
HETATM   59  H20 UNL     1       2.649  -5.045   0.478  1.00  0.00           H  
HETATM   60  H21 UNL     1       3.197  -3.821  -0.773  1.00  0.00           H  
HETATM   61  H22 UNL     1       5.855  -2.845   1.476  1.00  0.00           H  
HETATM   62  H23 UNL     1       5.624  -4.602   1.836  1.00  0.00           H  
HETATM   63  H24 UNL     1       5.094  -3.400   3.044  1.00  0.00           H  
HETATM   64  H25 UNL     1       0.120  -0.922  -1.592  1.00  0.00           H  
HETATM   65  H26 UNL     1       0.109  -2.553  -0.874  1.00  0.00           H  
HETATM   66  H27 UNL     1      -2.957  -1.997   0.958  1.00  0.00           H  
HETATM   67  H28 UNL     1      -1.592  -3.112   0.904  1.00  0.00           H  
HETATM   68  H29 UNL     1      -1.837  -3.070  -1.699  1.00  0.00           H  
HETATM   69  H30 UNL     1      -4.692  -3.012   0.772  1.00  0.00           H  
HETATM   70  H31 UNL     1      -5.837  -3.246  -0.584  1.00  0.00           H  
HETATM   71  H32 UNL     1      -5.116  -1.611  -0.260  1.00  0.00           H  
HETATM   72  H33 UNL     1      -3.298  -3.813  -3.168  1.00  0.00           H  
HETATM   73  H34 UNL     1      -4.796  -2.744  -3.089  1.00  0.00           H  
HETATM   74  H35 UNL     1      -4.805  -4.480  -2.481  1.00  0.00           H  
HETATM   75  H36 UNL     1       0.896   1.178   4.918  1.00  0.00           H  
HETATM   76  H37 UNL     1       0.071  -1.494   4.929  1.00  0.00           H  
HETATM   77  H38 UNL     1       1.625  -0.781   5.365  1.00  0.00           H  
HETATM   78  H39 UNL     1       1.366  -1.422   3.739  1.00  0.00           H  
HETATM   79  H40 UNL     1      -1.468  -0.400   5.084  1.00  0.00           H  
HETATM   80  H41 UNL     1      -1.169   1.242   5.617  1.00  0.00           H  
HETATM   81  H42 UNL     1      -1.770   1.068   3.976  1.00  0.00           H  
HETATM   82  H43 UNL     1      -2.386   3.164  -0.602  1.00  0.00           H  
HETATM   83  H44 UNL     1      -0.894   2.864  -1.551  1.00  0.00           H  
HETATM   84  H45 UNL     1      -2.243   1.245  -3.074  1.00  0.00           H  
HETATM   85  H46 UNL     1      -4.294   2.766  -4.713  1.00  0.00           H  
HETATM   86  H47 UNL     1      -4.319   1.060  -4.023  1.00  0.00           H  
HETATM   87  H48 UNL     1      -5.672   2.189  -3.625  1.00  0.00           H  
HETATM   88  H49 UNL     1      -4.430   3.264  -0.694  1.00  0.00           H  
HETATM   89  H50 UNL     1      -5.428   3.817  -2.050  1.00  0.00           H  
HETATM   90  H51 UNL     1      -3.826   4.548  -1.785  1.00  0.00           H  
HETATM   91  H52 UNL     1      -3.847   0.227  -0.973  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3    4    4
CONECT    3   43   44   45
CONECT    4    5   46
CONECT    5    6   47   48
CONECT    6    7   49   50
CONECT    7    8    9   24
CONECT    8   51   52   53
CONECT    9   10   15   54
CONECT   10   11   55   56
CONECT   11   12   12   57
CONECT   12   13   14
CONECT   13   58   59   60
CONECT   14   61   62   63
CONECT   15   16   64   65
CONECT   16   17   22   38
CONECT   17   18   66   67
CONECT   18   19   19   68
CONECT   19   20   21
CONECT   20   69   70   71
CONECT   21   72   73   74
CONECT   22   23   23   24
CONECT   24   25   30
CONECT   25   26   26   27
CONECT   27   28   29   75
CONECT   28   76   77   78
CONECT   29   79   80   81
CONECT   30   31   31   32
CONECT   32   33   38   38
CONECT   33   34   82   83
CONECT   34   35   35   84
CONECT   35   36   37
CONECT   36   85   86   87
CONECT   37   88   89   90
CONECT   38   39
CONECT   39   91
END

HMDB0030463
     RDKit          3D
Hyperforin
 91 92  0  0  0  0  0  0  0  0999 V2000
    4.3680    3.6244   -1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112    3.5576   -2.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4037    4.1209   -3.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439    3.0298   -1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9198    2.4790   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858    1.0342   -0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083    0.2195    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.3679    1.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -1.2112    0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7031   -2.3560    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0079   -2.5347    1.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764   -3.4858    1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784   -4.3898    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -3.5955    1.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0839   -1.4590   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345   -1.1090    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605   -2.2812    0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938   -2.8111   -0.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8537   -3.0046   -1.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -2.6885   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2129   -3.5545   -2.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423   -0.6343    1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -1.1176    2.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2078    0.5340    1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391    1.0319    2.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    2.1590    2.8070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    0.4770    4.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820   -0.8491    4.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    0.5808    4.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    1.5849    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133    2.7179    1.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955    1.3107   -0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8406    2.3982   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168    1.9937   -2.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    2.5469   -2.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5756    2.1214   -3.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3851    3.5899   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741    0.0341   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798   -0.2022   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2057    4.1248   -1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    2.6172   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632    4.2373   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    3.3357   -4.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    4.8222   -3.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791    4.7103   -3.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    2.9958   -2.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966    3.1411   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618    2.6456   -0.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    0.9703   -1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4226    0.5847   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    0.1611    2.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4970   -0.2109    0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0435    1.4601    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703   -1.1878   -0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8944   -2.5833    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5852   -3.3277    0.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3222   -1.9300    2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3454   -5.0594   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489   -5.0447    0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -3.8208   -0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -2.8448    1.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239   -4.6018    1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0942   -3.4003    3.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -0.9218   -1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093   -2.5531   -0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -1.9974    0.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5915   -3.1124    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372   -3.0697   -1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6917   -3.0123    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8365   -3.2459   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158   -1.6113   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976   -3.8130   -3.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7958   -2.7441   -3.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8046   -4.4798   -2.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8956    1.1780    4.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706   -1.4937    4.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -0.7805    5.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662   -1.4216    3.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4676   -0.4004    5.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1686    1.2423    5.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7697    1.0685    3.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3858    3.1640   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8940    2.8643   -1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    1.2452   -3.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2942    2.7660   -4.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3190    1.0600   -4.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6721    2.1885   -3.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    3.2642   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4278    3.8165   -2.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261    4.5480   -1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8468    0.2274   -0.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 24 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  3
 35 36  1  0
 35 37  1  0
 32 38  2  0
 38 39  1  0
 24  7  1  0
 38 16  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  0
  6 50  1  0
  8 51  1  0
  8 52  1  0
  8 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 13 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 17 66  1  0
 17 67  1  0
 18 68  1  0
 20 69  1  0
 20 70  1  0
 20 71  1  0
 21 72  1  0
 21 73  1  0
 21 74  1  0
 27 75  1  0
 28 76  1  0
 28 77  1  0
 28 78  1  0
 29 79  1  0
 29 80  1  0
 29 81  1  0
 33 82  1  0
 33 83  1  0
 34 84  1  0
 36 85  1  0
 36 86  1  0
 36 87  1  0
 37 88  1  0
 37 89  1  0
 37 90  1  0
 39 91  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hiperforina	HMDB
Hyperforine	HMDB
Tetrahydrohyperforin	MeSH
Hyperforin	MeSH
Octahydrohyperforin	MeSH

Chemical Formula

C₃₅H₅₂O₄

Average Molecular Weight

536.785

Monoisotopic Molecular Weight

536.386560152

IUPAC Name

4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

Traditional Name

4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

CAS Registry Number

11079-53-1

SMILES

CC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O

InChI Identifier

InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3

InChI Key

KGSZHKRKHXOAMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Cyclohexenone
Vinylogous acid
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030463)

Source

Exogenous

Exogenous (HMDB: HMDB0030463)

Food

Food (HMDB: HMDB0030463)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Endogenous (HMDB: HMDB0030463)

Plant

Plant (HMDB: HMDB0030463)

Animal

Animal (HMDB: HMDB0030463)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030463)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030463)

Lipid metabolism pathway (HMDB: HMDB0030463)

Cellular process

Cell signaling (HMDB: HMDB0030463)

Biochemical process

Lipid transport (HMDB: HMDB0030463)

Role

Biological role

Energy source (HMDB: HMDB0030463)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0030463)

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030463)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0030463)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	79 - 80 °C	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	0.0006 g/L	ALOGPS
logP	6.32	ALOGPS
logP	9.67	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	7.17	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	166.68 m³·mol⁻¹	ChemAxon
Polarizability	63.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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-2H]-	266.293	30932474
DeepCCS	[M+Na]+	241.716	30932474
AllCCS	[M+H]+	230.6	32859911
AllCCS	[M+H-H2O]+	229.2	32859911
AllCCS	[M+NH4]+	231.9	32859911
AllCCS	[M+Na]+	232.3	32859911
AllCCS	[M-H]-	246.9	32859911
AllCCS	[M+Na-2H]-	249.4	32859911
AllCCS	[M+HCOO]-	252.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.15 minutes	32390414
Predicted by Siyang on May 30, 2022	24.8702 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4661.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	549.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	318.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	229.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1082.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1000.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2013.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	941.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1680.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	657.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	641.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	98.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hyperforin	CC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O	4292.9	Standard polar	33892256
Hyperforin	CC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O	3363.5	Standard non polar	33892256
Hyperforin	CC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O	3124.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hyperforin,1TMS,isomer #1	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(=O)C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C	3478.2	Semi standard non polar	33892256
Hyperforin,1TMS,isomer #2	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O	3542.6	Semi standard non polar	33892256
Hyperforin,2TMS,isomer #1	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C	3500.6	Semi standard non polar	33892256
Hyperforin,2TMS,isomer #1	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C	3469.5	Standard non polar	33892256
Hyperforin,1TBDMS,isomer #1	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(=O)C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C(C)(C)C	3723.2	Semi standard non polar	33892256
Hyperforin,1TBDMS,isomer #2	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O	3805.5	Semi standard non polar	33892256
Hyperforin,2TBDMS,isomer #1	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C(C)(C)C	3981.8	Semi standard non polar	33892256
Hyperforin,2TBDMS,isomer #1	CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C(=O)C(CC=C(C)C)=C2O[Si](C)(C)C(C)(C)C	3846.6	Standard non polar	33892256

Spectra

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hyperforin

METLIN ID

Not Available

PubChem Compound

3662

PDB ID

Not Available

ChEBI ID

5834

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

Hammer KD, Hillwig ML, Solco AK, Dixon PM, Delate K, Murphy PA, Wurtele ES, Birt DF: Inhibition of prostaglandin E(2) production by anti-inflammatory hypericum perforatum extracts and constituents in RAW264.7 Mouse Macrophage Cells. J Agric Food Chem. 2007 Sep 5;55(18):7323-31. Epub 2007 Aug 15. [PubMed:17696442 ]
Sun F, Liu JY, He F, Liu Z, Wang R, Wang DM, Wang YF, Yang DP: In-vitro antitumor activity evaluation of hyperforin derivatives. J Asian Nat Prod Res. 2011 Aug;13(8):688-99. doi: 10.1080/10286020.2011.584532. [PubMed:21751836 ]
Hubner AT: Treatment with Hypericum perforatum L. does not trigger decreased resistance in Staphylococcus aureus against antibiotics and hyperforin. Phytomedicine. 2003 Mar;10(2-3):206-8. [PubMed:12725578 ]
Muruganandam AV, Bhattacharya SK, Ghosal S: Antidepressant activity of hyperforin conjugates of the St. John's wort, Hypericum perforatum Linn.: an experimental study. Indian J Exp Biol. 2001 Dec;39(12):1302-4. [PubMed:12018529 ]
Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Muller WE: Hyperforin as a possible antidepressant component of hypericum extracts. Life Sci. 1998;63(6):499-510. [PubMed:9718074 ]
Moore LB, Goodwin B, Jones SA, Wisely GB, Serabjit-Singh CJ, Willson TM, Collins JL, Kliewer SA: St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7500-2. [PubMed:10852961 ]
Leuner K, Kazanski V, Muller M, Essin K, Henke B, Gollasch M, Harteneck C, Muller WE: Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels. FASEB J. 2007 Dec;21(14):4101-11. Epub 2007 Jul 31. [PubMed:17666455 ]
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.

Enzymes

Enzyme Details

1. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Nuclear receptor subfamily 1 group I member 2

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular weight:: 49761.2

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Tirona RG, Leake BF, Wolkoff AW, Kim RB: Human organic anion transporting polypeptide-C (SLC21A6) is a major determinant of rifampin-mediated pregnane X receptor activation. J Pharmacol Exp Ther. 2003 Jan;304(1):223-8. [PubMed:12490595 ]

Enzyme Details

2. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Kast HR, Goodwin B, Tarr PT, Jones SA, Anisfeld AM, Stoltz CM, Tontonoz P, Kliewer S, Willson TM, Edwards PA: Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. J Biol Chem. 2002 Jan 25;277(4):2908-15. Epub 2001 Nov 12. [PubMed:11706036 ]

Showing metabocard for Hyperforin (HMDB0030463)

MOL for HMDB0030463 (Hyperforin)

3D MOL for HMDB0030463 (Hyperforin)

3D SDF for HMDB0030463 (Hyperforin)

3D-SDF for HMDB0030463 (Hyperforin)

PDB for HMDB0030463 (Hyperforin)

3D PDB for HMDB0030463 (Hyperforin)

SMILES for HMDB0030463 (Hyperforin)

INCHI for HMDB0030463 (Hyperforin)

Structure for HMDB0030463 (Hyperforin)

3D Structure for HMDB0030463 (Hyperforin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

Transporters

References

References