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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:22 UTC

Update Date

2022-03-07 02:52:24 UTC

HMDB ID

HMDB0030041

Secondary Accession Numbers

HMDB30041

Metabolite Identification

Common Name

Lupulone

Description

Lupulone, also known as b'' -acid or b-bitter acid, belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively. Based on a literature review a significant number of articles have been published on Lupulone.

Structure

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

  Mrv0541 05061304592D          

 30 30  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  2  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
 17 11  2  0  0  0  0
 18  5  1  0  0  0  0
 18  6  1  0  0  0  0
 18 12  2  0  0  0  0
 19  7  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 21  1  0  0  0  0
 23 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 20  1  0  0  0  0
 25 22  2  0  0  0  0
 26 13  1  0  0  0  0
 26 14  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 21  2  0  0  0  0
 28 23  2  0  0  0  0
 29 24  2  0  0  0  0
 30 25  1  0  0  0  0
M  END

HMDB0030041
     RDKit          3D
Lupulone
 68 68  0  0  0  0  0  0  0  0999 V2000
   -0.6101    5.6255   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235    4.2435   -1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343    3.7922   -2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    3.4213   -0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6723    2.0111   -1.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351    1.0294   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    1.1757    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    2.2908    1.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.1136    0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    0.4280    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564   -0.5038    1.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    1.7831    1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    1.7884    2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862    1.3984    1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    3.1933    2.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908   -1.0884    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -2.0683    0.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0197   -1.4996   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678   -2.2200    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735   -3.4104    1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7311   -3.4792    2.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -4.6867    3.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -2.3863    3.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.4070   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9107   -2.9124   -2.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741   -2.6347   -3.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2674   -3.1169   -4.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.8177   -4.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488   -0.3289   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -0.4889   -1.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723    5.7934    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    6.2993   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    5.9081   -0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0270    3.5032   -3.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9968    2.9115   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    4.5877   -2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681    3.7323   -0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.8410   -1.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119    1.9341   -1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    1.2416    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1319    2.5588    0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199    1.9918    2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.0921    3.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6637    1.9357    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    0.3088    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3709    1.6939    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645    3.8872    1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829    3.1979    3.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061    3.5322    3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -2.4340   -0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -2.4248    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -1.4903    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8175   -4.2636    0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -4.4700    3.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -5.5751    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2563   -4.9217    4.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7418   -2.6883    4.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534   -1.4509    3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0983   -2.1066    3.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -1.8772   -2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -3.2674   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -3.5085   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082   -3.8869   -4.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169   -3.5781   -3.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081   -2.3078   -4.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601   -0.8517   -3.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437   -1.6783   -5.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1036   -2.4146   -4.0906 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 18 29  1  0
 29 30  2  0
 29  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

  Mrv0541 05061304592D          

 30 30  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  2  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
 17 11  2  0  0  0  0
 18  5  1  0  0  0  0
 18  6  1  0  0  0  0
 18 12  2  0  0  0  0
 19  7  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 21  1  0  0  0  0
 23 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 20  1  0  0  0  0
 25 22  2  0  0  0  0
 26 13  1  0  0  0  0
 26 14  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 21  2  0  0  0  0
 28 23  2  0  0  0  0
 29 24  2  0  0  0  0
 30 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030041

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19-20,30H,10,13-15H2,1-8H3

> <INCHI_KEY>
WYJNATSMJAUNMZ-UHFFFAOYSA-N

> <FORMULA>
C26H38O4

> <MOLECULAR_WEIGHT>
414.5775

> <EXACT_MASS>
414.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
48.37498841431003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
6.784303402

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.240615780490405

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.510938764864557

> <JCHEM_PKA_STRONGEST_BASIC>
-7.772067058923357

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
126.58289999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030041
     RDKit          3D
Lupulone
 68 68  0  0  0  0  0  0  0  0999 V2000
   -0.6101    5.6255   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235    4.2435   -1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343    3.7922   -2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    3.4213   -0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6723    2.0111   -1.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351    1.0294   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    1.1757    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    2.2908    1.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.1136    0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    0.4280    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564   -0.5038    1.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    1.7831    1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    1.7884    2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862    1.3984    1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    3.1933    2.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908   -1.0884    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -2.0683    0.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0197   -1.4996   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678   -2.2200    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735   -3.4104    1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7311   -3.4792    2.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -4.6867    3.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -2.3863    3.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.4070   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9107   -2.9124   -2.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741   -2.6347   -3.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2674   -3.1169   -4.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.8177   -4.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488   -0.3289   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -0.4889   -1.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723    5.7934    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    6.2993   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    5.9081   -0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0270    3.5032   -3.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9968    2.9115   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    4.5877   -2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681    3.7323   -0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.8410   -1.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119    1.9341   -1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    1.2416    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1319    2.5588    0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199    1.9918    2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.0921    3.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6637    1.9357    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    0.3088    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3709    1.6939    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645    3.8872    1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829    3.1979    3.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061    3.5322    3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -2.4340   -0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -2.4248    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -1.4903    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8175   -4.2636    0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -4.4700    3.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -5.5751    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2563   -4.9217    4.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7418   -2.6883    4.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534   -1.4509    3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0983   -2.1066    3.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -1.8772   -2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -3.2674   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -3.5085   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082   -3.8869   -4.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169   -3.5781   -3.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081   -2.3078   -4.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601   -0.8517   -3.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437   -1.6783   -5.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1036   -2.4146   -4.0906 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 18 29  1  0
 29 30  2  0
 29  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.679   4.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.636   5.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.347   4.135   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.303   5.849   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.173   3.222   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.840   3.222   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.163   4.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.830   4.402   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   17                                                            
CONECT    5   18                                                            
CONECT    6   18                                                            
CONECT    7   19                                                            
CONECT    8   19                                                            
CONECT    9   10   16                                                       
CONECT   10    9   20                                                       
CONECT   11   13   17                                                       
CONECT   12   14   18                                                       
CONECT   13   11   26                                                       
CONECT   14   12   26                                                       
CONECT   15   19   21                                                       
CONECT   16    1    2    9                                                  
CONECT   17    3    4   11                                                  
CONECT   18    5    6   12                                                  
CONECT   19    7    8   15                                                  
CONECT   20   10   23   24                                                  
CONECT   21   15   22   27                                                  
CONECT   22   21   23   25                                                  
CONECT   23   20   22   28                                                  
CONECT   24   20   26   29                                                  
CONECT   25   22   26   30                                                  
CONECT   26   13   14   24   25                                             
CONECT   27   21                                                            
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   25                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

COMPND    HMDB0030041
HETATM    1  C1  UNL     1      -0.610   5.625  -0.591  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.624   4.244  -1.124  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.434   3.792  -2.048  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.585   3.421  -0.768  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.672   2.011  -1.259  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.635   1.029  -0.117  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.383   1.176   0.633  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.220   2.291   1.212  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.599   0.114   0.705  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.914   0.428   1.245  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.756  -0.504   1.303  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.265   1.783   1.711  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.698   1.788   2.212  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.686   1.398   1.165  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.961   3.193   2.752  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.291  -1.088   0.289  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.280  -2.068   0.386  1.00  0.00           O  
HETATM   18  C15 UNL     1      -1.020  -1.500  -0.277  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.768  -2.220   0.824  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.073  -3.410   1.319  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.731  -3.479   2.592  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.028  -4.687   3.087  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.025  -2.386   3.556  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.720  -2.407  -1.445  1.00  0.00           C  
HETATM   25  C22 UNL     1      -1.911  -2.912  -2.132  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.074  -2.635  -3.419  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.267  -3.117  -4.190  1.00  0.00           C  
HETATM   28  C25 UNL     1      -1.060  -1.818  -4.165  1.00  0.00           C  
HETATM   29  C26 UNL     1      -1.849  -0.329  -0.649  1.00  0.00           C  
HETATM   30  O4  UNL     1      -2.754  -0.489  -1.433  1.00  0.00           O  
HETATM   31  H1  UNL     1      -1.372   5.793   0.184  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.878   6.299  -1.445  1.00  0.00           H  
HETATM   33  H3  UNL     1       0.413   5.908  -0.212  1.00  0.00           H  
HETATM   34  H4  UNL     1       0.027   3.503  -3.050  1.00  0.00           H  
HETATM   35  H5  UNL     1       0.997   2.912  -1.688  1.00  0.00           H  
HETATM   36  H6  UNL     1       1.188   4.588  -2.239  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.368   3.732  -0.094  1.00  0.00           H  
HETATM   38  H8  UNL     1      -0.836   1.841  -1.933  1.00  0.00           H  
HETATM   39  H9  UNL     1      -2.612   1.934  -1.844  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.463   1.242   0.625  1.00  0.00           H  
HETATM   41  H11 UNL     1       2.132   2.559   0.946  1.00  0.00           H  
HETATM   42  H12 UNL     1       1.620   1.992   2.615  1.00  0.00           H  
HETATM   43  H13 UNL     1       3.737   1.092   3.079  1.00  0.00           H  
HETATM   44  H14 UNL     1       5.664   1.936   1.335  1.00  0.00           H  
HETATM   45  H15 UNL     1       4.943   0.309   1.213  1.00  0.00           H  
HETATM   46  H16 UNL     1       4.371   1.694   0.142  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.165   3.887   1.890  1.00  0.00           H  
HETATM   48  H18 UNL     1       4.783   3.198   3.495  1.00  0.00           H  
HETATM   49  H19 UNL     1       3.006   3.532   3.203  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.668  -2.434  -0.456  1.00  0.00           H  
HETATM   51  H21 UNL     1      -2.784  -2.425   0.431  1.00  0.00           H  
HETATM   52  H22 UNL     1      -1.885  -1.490   1.647  1.00  0.00           H  
HETATM   53  H23 UNL     1      -0.818  -4.264   0.678  1.00  0.00           H  
HETATM   54  H24 UNL     1       1.080  -4.470   3.067  1.00  0.00           H  
HETATM   55  H25 UNL     1      -0.276  -5.575   2.490  1.00  0.00           H  
HETATM   56  H26 UNL     1      -0.256  -4.922   4.141  1.00  0.00           H  
HETATM   57  H27 UNL     1      -0.742  -2.688   4.581  1.00  0.00           H  
HETATM   58  H28 UNL     1      -0.453  -1.451   3.288  1.00  0.00           H  
HETATM   59  H29 UNL     1      -2.098  -2.107   3.573  1.00  0.00           H  
HETATM   60  H30 UNL     1      -0.055  -1.877  -2.124  1.00  0.00           H  
HETATM   61  H31 UNL     1      -0.145  -3.267  -1.029  1.00  0.00           H  
HETATM   62  H32 UNL     1      -2.685  -3.509  -1.661  1.00  0.00           H  
HETATM   63  H33 UNL     1      -2.908  -3.887  -4.904  1.00  0.00           H  
HETATM   64  H34 UNL     1      -4.017  -3.578  -3.526  1.00  0.00           H  
HETATM   65  H35 UNL     1      -3.708  -2.308  -4.802  1.00  0.00           H  
HETATM   66  H36 UNL     1      -0.860  -0.852  -3.694  1.00  0.00           H  
HETATM   67  H37 UNL     1      -1.344  -1.678  -5.207  1.00  0.00           H  
HETATM   68  H38 UNL     1      -0.104  -2.415  -4.091  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4    4
CONECT    3   34   35   36
CONECT    4    5   37
CONECT    5    6   38   39
CONECT    6    7   29   40
CONECT    7    8    8    9
CONECT    9   10   16   16
CONECT   10   11   11   12
CONECT   12   13   41   42
CONECT   13   14   15   43
CONECT   14   44   45   46
CONECT   15   47   48   49
CONECT   16   17   18
CONECT   17   50
CONECT   18   19   24   29
CONECT   19   20   51   52
CONECT   20   21   21   53
CONECT   21   22   23
CONECT   22   54   55   56
CONECT   23   57   58   59
CONECT   24   25   60   61
CONECT   25   26   26   62
CONECT   26   27   28
CONECT   27   63   64   65
CONECT   28   66   67   68
CONECT   29   30   30
END

HMDB0030041
     RDKit          3D
Lupulone
 68 68  0  0  0  0  0  0  0  0999 V2000
   -0.6101    5.6255   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235    4.2435   -1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343    3.7922   -2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    3.4213   -0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6723    2.0111   -1.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351    1.0294   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    1.1757    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    2.2908    1.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    0.1136    0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    0.4280    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564   -0.5038    1.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    1.7831    1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    1.7884    2.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862    1.3984    1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9611    3.1933    2.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908   -1.0884    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -2.0683    0.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0197   -1.4996   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678   -2.2200    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735   -3.4104    1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7311   -3.4792    2.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -4.6867    3.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -2.3863    3.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -2.4070   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9107   -2.9124   -2.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741   -2.6347   -3.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2674   -3.1169   -4.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.8177   -4.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488   -0.3289   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -0.4889   -1.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723    5.7934    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    6.2993   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    5.9081   -0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0270    3.5032   -3.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9968    2.9115   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    4.5877   -2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681    3.7323   -0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.8410   -1.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119    1.9341   -1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    1.2416    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1319    2.5588    0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199    1.9918    2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.0921    3.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6637    1.9357    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    0.3088    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3709    1.6939    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645    3.8872    1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829    3.1979    3.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061    3.5322    3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -2.4340   -0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -2.4248    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -1.4903    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8175   -4.2636    0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -4.4700    3.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -5.5751    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2563   -4.9217    4.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7418   -2.6883    4.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534   -1.4509    3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0983   -2.1066    3.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -1.8772   -2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -3.2674   -1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -3.5085   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082   -3.8869   -4.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169   -3.5781   -3.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081   -2.3078   -4.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601   -0.8517   -3.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437   -1.6783   -5.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1036   -2.4146   -4.0906 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 18 29  1  0
 29 30  2  0
 29  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
B'' -acid	HMDB
b-Bitter acid	HMDB
b-Lupulic acid	HMDB
b-Lupulinic acid	HMDB
beta-Bitter acid	HMDB
beta-Lupulic acid	HMDB
Lupulon	HMDB

Chemical Formula

C₂₆H₃₈O₄

Average Molecular Weight

414.5775

Monoisotopic Molecular Weight

414.277009704

IUPAC Name

5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione

Traditional Name

5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione

CAS Registry Number

468-28-0

SMILES

CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O

InChI Identifier

InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19-20,30H,10,13-15H2,1-8H3

InChI Key

WYJNATSMJAUNMZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

M-benzoquinones

Alternative Parents

Substituents

M-benzoquinone
Cyclohexenone
1,3-diketone
1,3-dicarbonyl compound
Vinylogous acid
Enol
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030041)
Cell membrane (HMDB: HMDB0030041)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030041)

Source

Endogenous

Endogenous (HMDB: HMDB0030041)

Exogenous

Food

Food (HMDB: HMDB0030041)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0030041)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	93 °C	Not Available
Boiling Point	583.00 to 584.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.002 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.548 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0049 g/L	ALOGPS
logP	4.53	ALOGPS
logP	6.78	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	2.51	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.58 m³·mol⁻¹	ChemAxon
Polarizability	48.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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+H]+	216.988	30932474
DeepCCS	[M-H]-	214.63	30932474
DeepCCS	[M-2H]-	248.854	30932474
DeepCCS	[M+Na]+	224.083	30932474
AllCCS	[M+H]+	202.8	32859911
AllCCS	[M+H-H2O]+	200.6	32859911
AllCCS	[M+NH4]+	204.9	32859911
AllCCS	[M+Na]+	205.4	32859911
AllCCS	[M-H]-	213.8	32859911
AllCCS	[M+Na-2H]-	215.0	32859911
AllCCS	[M+HCOO]-	216.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lupulone	CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O	3523.6	Standard polar	33892256
Lupulone	CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O	2521.4	Standard non polar	33892256
Lupulone	CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O	2479.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lupulone,1TMS,isomer #1	CC(C)=CCC1C(=O)C(C(=O)CC(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2743.0	Semi standard non polar	33892256
Lupulone,1TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C1=O	2712.3	Semi standard non polar	33892256
Lupulone,1TMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	2730.5	Semi standard non polar	33892256
Lupulone,1TMS,isomer #4	CC(C)=CCC1C(=O)C(C(=CC(C)C)O[Si](C)(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	2839.7	Semi standard non polar	33892256
Lupulone,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2730.6	Semi standard non polar	33892256
Lupulone,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2692.6	Standard non polar	33892256
Lupulone,2TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C1=O	2754.3	Semi standard non polar	33892256
Lupulone,2TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C1=O	2687.5	Standard non polar	33892256
Lupulone,2TMS,isomer #3	CC(C)=CCC1C(=O)C(C(=CC(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2799.6	Semi standard non polar	33892256
Lupulone,2TMS,isomer #3	CC(C)=CCC1C(=O)C(C(=CC(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2822.3	Standard non polar	33892256
Lupulone,2TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C1=O	2786.6	Semi standard non polar	33892256
Lupulone,2TMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C1=O	2769.8	Standard non polar	33892256
Lupulone,2TMS,isomer #5	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	2811.0	Semi standard non polar	33892256
Lupulone,2TMS,isomer #5	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	2784.1	Standard non polar	33892256
Lupulone,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2765.9	Semi standard non polar	33892256
Lupulone,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2803.7	Standard non polar	33892256
Lupulone,3TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C1=O	2777.8	Semi standard non polar	33892256
Lupulone,3TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C1=O	2807.8	Standard non polar	33892256
Lupulone,1TBDMS,isomer #1	CC(C)=CCC1C(=O)C(C(=O)CC(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	2984.0	Semi standard non polar	33892256
Lupulone,1TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C1=O	2952.2	Semi standard non polar	33892256
Lupulone,1TBDMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	2963.1	Semi standard non polar	33892256
Lupulone,1TBDMS,isomer #4	CC(C)=CCC1C(=O)C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	3059.9	Semi standard non polar	33892256
Lupulone,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	3189.5	Semi standard non polar	33892256
Lupulone,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	3058.6	Standard non polar	33892256
Lupulone,2TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C1=O	3211.2	Semi standard non polar	33892256
Lupulone,2TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C1=O	3056.2	Standard non polar	33892256
Lupulone,2TBDMS,isomer #3	CC(C)=CCC1C(=O)C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	3249.6	Semi standard non polar	33892256
Lupulone,2TBDMS,isomer #3	CC(C)=CCC1C(=O)C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	3192.6	Standard non polar	33892256
Lupulone,2TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C1=O	3234.2	Semi standard non polar	33892256
Lupulone,2TBDMS,isomer #4	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C1=O	3162.8	Standard non polar	33892256
Lupulone,2TBDMS,isomer #5	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	3265.5	Semi standard non polar	33892256
Lupulone,2TBDMS,isomer #5	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O	3172.9	Standard non polar	33892256
Lupulone,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	3409.6	Semi standard non polar	33892256
Lupulone,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C1=O	3326.4	Standard non polar	33892256
Lupulone,3TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C1=O	3426.8	Semi standard non polar	33892256
Lupulone,3TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C1=O	3328.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lupulone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0072-4139000000-0bf669d56b1c9b4f4c04	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lupulone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6011900000-63c192248b05841e5078	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lupulone 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 - Lupulone 10V, Positive-QTOF	splash10-01ba-2009400000-0ba9b293596baa5ddb63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 20V, Positive-QTOF	splash10-0ap1-5019000000-c80e4880a1faca266006	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 40V, Positive-QTOF	splash10-00ls-9212000000-20e2fe715431dd66ef45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 10V, Negative-QTOF	splash10-03di-0004900000-a12295f037d82cc69c72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 20V, Negative-QTOF	splash10-03fs-3019400000-c3a9cccfd426897399da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 40V, Negative-QTOF	splash10-052b-4339000000-2039958c128e5ce3a809	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 10V, Negative-QTOF	splash10-03di-0000900000-d3fba9340173b668896d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 20V, Negative-QTOF	splash10-03di-0003900000-ebb1764d16b20c75b809	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 40V, Negative-QTOF	splash10-002r-1098000000-33fe63ee2ea117ea5878	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 10V, Positive-QTOF	splash10-014j-0047900000-31707e6219c0a4205ff3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 20V, Positive-QTOF	splash10-0006-1097200000-78a9cec5cec0f63c1e53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lupulone 40V, Positive-QTOF	splash10-000l-2492000000-8e74b55ee1d318d2425d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

Not Available

METLIN ID

Not Available

PubChem Compound

51397980

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1039101

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lamy V, Roussi S, Chaabi M, Gosse F, Lobstein A, Raul F: Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. Apoptosis. 2008 Oct;13(10):1232-42. doi: 10.1007/s10495-008-0250-5. [PubMed:18726190 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Lupulone (HMDB0030041)

MOL for HMDB0030041 (Lupulone)

3D MOL for HMDB0030041 (Lupulone)

3D SDF for HMDB0030041 (Lupulone)

3D-SDF for HMDB0030041 (Lupulone)

PDB for HMDB0030041 (Lupulone)

3D PDB for HMDB0030041 (Lupulone)

SMILES for HMDB0030041 (Lupulone)

INCHI for HMDB0030041 (Lupulone)

Structure for HMDB0030041 (Lupulone)

3D Structure for HMDB0030041 (Lupulone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra