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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:17 UTC

Update Date

2022-03-07 02:52:24 UTC

HMDB ID

HMDB0030026

Secondary Accession Numbers

HMDB30026

Metabolite Identification

Common Name

Isohumulone A

Description

Isohumulone A, also known as photoisohumulone, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Based on a literature review a small amount of articles have been published on Isohumulone A.

Structure

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


  Mrv0541 05061304582D          

 26 26  0  0  0  0            999 V2000
   -2.4535    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5785    4.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    4.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2814    3.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2707    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264    3.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    1.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  7  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
 21 15  1  0  0  0  0
 21 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 19  2  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
M  END

HMDB0030026
     RDKit          3D
Isohumulone A
 56 56  0  0  0  0  0  0  0  0999 V2000
    4.3884    0.9382   -0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -0.5068   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9221   -1.0796   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -1.2707   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095   -0.7678   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -0.9545    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -1.5614    1.7852 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971   -0.5140    1.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -0.7687    2.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769    0.9907    1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    1.8905    1.8930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122    1.3241    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091    2.7381    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    3.6867    0.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407    3.0233   -0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8155    4.5143   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    5.1444    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    4.8543   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394    0.1434    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    0.0448   -0.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -1.0552    0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -2.0312   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542   -3.2867    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8527   -4.4632   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -5.6937    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2915   -4.6232   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117    1.0950   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632    1.4463   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    1.4405   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467   -1.1636    0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -2.1469   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -0.5471   -1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -2.3246   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -1.3807   -1.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509    0.2799   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019   -0.2095    3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    2.6065    2.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    2.6366   -1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333    2.5283    0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493    4.9588   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    5.9978    1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9607    5.5015    1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354    4.3805    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228    5.9013   -0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305    4.1183   -0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8025    4.8081   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -1.4449    1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6663   -1.5228   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0723   -2.2996   -0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7963   -3.2624    0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644   -6.3867   -0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -5.4926    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576   -6.1927    1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6126   -5.6773   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -4.3775   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9416   -3.9869    0.2399 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 21  8  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  9 36  1  0
 11 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
M  END


  Mrv0541 05061304582D          

 26 26  0  0  0  0            999 V2000
   -2.4535    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5785    4.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7805    4.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2814    3.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2707    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264    3.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    1.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  7  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
 21 15  1  0  0  0  0
 21 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 19  2  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030026

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3

> <INCHI_KEY>
QARXXMMQVDCYGZ-UHFFFAOYSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.4599

> <EXACT_MASS>
362.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.994058256689186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
3.9096914630000006

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.88975276214697

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.5622788019661003

> <JCHEM_PKA_STRONGEST_BASIC>
-4.370488344465941

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
104.07449999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isohumulone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030026
     RDKit          3D
Isohumulone A
 56 56  0  0  0  0  0  0  0  0999 V2000
    4.3884    0.9382   -0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -0.5068   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9221   -1.0796   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -1.2707   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095   -0.7678   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -0.9545    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -1.5614    1.7852 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971   -0.5140    1.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -0.7687    2.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769    0.9907    1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    1.8905    1.8930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122    1.3241    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091    2.7381    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    3.6867    0.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407    3.0233   -0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8155    4.5143   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    5.1444    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    4.8543   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394    0.1434    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    0.0448   -0.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -1.0552    0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -2.0312   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542   -3.2867    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8527   -4.4632   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -5.6937    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2915   -4.6232   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117    1.0950   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632    1.4463   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    1.4405   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467   -1.1636    0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -2.1469   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -0.5471   -1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -2.3246   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -1.3807   -1.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509    0.2799   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019   -0.2095    3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    2.6065    2.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    2.6366   -1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333    2.5283    0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493    4.9588   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    5.9978    1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9607    5.5015    1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354    4.3805    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228    5.9013   -0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305    4.1183   -0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8025    4.8081   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -1.4449    1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6663   -1.5228   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0723   -2.2996   -0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7963   -3.2624    0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644   -6.3867   -0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -5.4926    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576   -6.1927    1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6126   -5.6773   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -4.3775   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9416   -3.9869    0.2399 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 21  8  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  9 36  1  0
 11 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  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      -4.580   2.603   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.404   0.066   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.080   8.443   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.457   7.618   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.703  -2.460   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.545  -4.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.795   0.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.525   5.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.505   4.689   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.267  -1.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.260   1.096   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.049   7.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.172  -2.621   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.477   2.904   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.090   3.224   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   14                                                            
CONECT    7    9   12                                                       
CONECT    8   10   13                                                       
CONECT    9    7   15                                                       
CONECT   10    8   17                                                       
CONECT   11   14   16                                                       
CONECT   12    1    2    7                                                  
CONECT   13    3    4    8                                                  
CONECT   14    5    6   11                                                  
CONECT   15    9   19   21                                                  
CONECT   16   11   18   22                                                  
CONECT   17   10   21   23                                                  
CONECT   18   16   19   20                                                  
CONECT   19   15   18   24                                                  
CONECT   20   18   21   25                                                  
CONECT   21   15   17   20   26                                             
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   21                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0030026
HETATM    1  C1  UNL     1       4.388   0.938  -0.971  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.549  -0.507  -0.666  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.922  -1.080  -0.679  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.527  -1.271  -0.391  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.110  -0.768  -0.359  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.510  -0.955   0.978  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.238  -1.561   1.785  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.197  -0.514   1.452  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.222  -0.769   2.879  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.077   0.991   1.358  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.002   1.890   1.893  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.012   1.324   0.706  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.409   2.738   0.448  1.00  0.00           C  
HETATM   14  O4  UNL     1      -0.702   3.687   0.854  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.641   3.023  -0.290  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.816   4.514  -0.410  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.908   5.144   0.957  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.045   4.854  -1.220  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.739   0.143   0.294  1.00  0.00           C  
HETATM   20  O5  UNL     1      -2.771   0.045  -0.405  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.029  -1.055   0.868  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.968  -2.031  -0.251  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.254  -3.287   0.009  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.853  -4.463  -0.057  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.068  -5.694   0.219  1.00  0.00           C  
HETATM   26  C21 UNL     1      -2.291  -4.623  -0.395  1.00  0.00           C  
HETATM   27  H1  UNL     1       3.712   1.095  -1.816  1.00  0.00           H  
HETATM   28  H2  UNL     1       5.363   1.446  -1.110  1.00  0.00           H  
HETATM   29  H3  UNL     1       3.918   1.441  -0.086  1.00  0.00           H  
HETATM   30  H4  UNL     1       6.347  -1.164   0.343  1.00  0.00           H  
HETATM   31  H5  UNL     1       5.874  -2.147  -1.047  1.00  0.00           H  
HETATM   32  H6  UNL     1       6.600  -0.547  -1.378  1.00  0.00           H  
HETATM   33  H7  UNL     1       3.651  -2.325  -0.169  1.00  0.00           H  
HETATM   34  H8  UNL     1       1.587  -1.381  -1.112  1.00  0.00           H  
HETATM   35  H9  UNL     1       2.051   0.280  -0.716  1.00  0.00           H  
HETATM   36  H10 UNL     1       1.002  -0.210   3.174  1.00  0.00           H  
HETATM   37  H11 UNL     1       0.736   2.606   2.568  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.568   2.637  -1.349  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.533   2.528   0.139  1.00  0.00           H  
HETATM   40  H14 UNL     1      -1.949   4.959  -0.957  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.194   5.998   1.027  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.961   5.502   1.089  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.735   4.381   1.753  1.00  0.00           H  
HETATM   44  H18 UNL     1      -4.323   5.901  -0.980  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.830   4.118  -0.940  1.00  0.00           H  
HETATM   46  H20 UNL     1      -3.802   4.808  -2.303  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.679  -1.445   1.715  1.00  0.00           H  
HETATM   48  H22 UNL     1      -0.666  -1.523  -1.174  1.00  0.00           H  
HETATM   49  H23 UNL     1      -2.072  -2.300  -0.486  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.796  -3.262   0.260  1.00  0.00           H  
HETATM   51  H25 UNL     1      -0.264  -6.387  -0.652  1.00  0.00           H  
HETATM   52  H26 UNL     1       1.030  -5.493   0.248  1.00  0.00           H  
HETATM   53  H27 UNL     1      -0.358  -6.193   1.157  1.00  0.00           H  
HETATM   54  H28 UNL     1      -2.613  -5.677  -0.287  1.00  0.00           H  
HETATM   55  H29 UNL     1      -2.413  -4.377  -1.482  1.00  0.00           H  
HETATM   56  H30 UNL     1      -2.942  -3.987   0.240  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    4    4
CONECT    3   30   31   32
CONECT    4    5   33
CONECT    5    6   34   35
CONECT    6    7    7    8
CONECT    8    9   10   21
CONECT    9   36
CONECT   10   11   12   12
CONECT   11   37
CONECT   12   13   19
CONECT   13   14   14   15
CONECT   15   16   38   39
CONECT   16   17   18   40
CONECT   17   41   42   43
CONECT   18   44   45   46
CONECT   19   20   20   21
CONECT   21   22   47
CONECT   22   23   48   49
CONECT   23   24   24   50
CONECT   24   25   26
CONECT   25   51   52   53
CONECT   26   54   55   56
END

HMDB0030026
     RDKit          3D
Isohumulone A
 56 56  0  0  0  0  0  0  0  0999 V2000
    4.3884    0.9382   -0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -0.5068   -0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9221   -1.0796   -0.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -1.2707   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095   -0.7678   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -0.9545    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2382   -1.5614    1.7852 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971   -0.5140    1.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -0.7687    2.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769    0.9907    1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025    1.8905    1.8930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122    1.3241    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091    2.7381    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021    3.6867    0.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407    3.0233   -0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8155    4.5143   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    5.1444    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446    4.8543   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394    0.1434    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    0.0448   -0.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -1.0552    0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -2.0312   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542   -3.2867    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8527   -4.4632   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -5.6937    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2915   -4.6232   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117    1.0950   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632    1.4463   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    1.4405   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467   -1.1636    0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -2.1469   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -0.5471   -1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -2.3246   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -1.3807   -1.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509    0.2799   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019   -0.2095    3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    2.6065    2.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680    2.6366   -1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333    2.5283    0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493    4.9588   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    5.9978    1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9607    5.5015    1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354    4.3805    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228    5.9013   -0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8305    4.1183   -0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8025    4.8081   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -1.4449    1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6663   -1.5228   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0723   -2.2996   -0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7963   -3.2624    0.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644   -6.3867   -0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -5.4926    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576   -6.1927    1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6126   -5.6773   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4126   -4.3775   -1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9416   -3.9869    0.2399 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  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  3
 24 25  1  0
 24 26  1  0
 21  8  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  9 36  1  0
 11 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isohumulone a2	HMDB
Photoisohumulone	HMDB
Isohumulone	HMDB
3,4-Dihydroxy-2-(3-methylbutanoyl)-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopenten-1-one	HMDB

Chemical Formula

C₂₁H₃₀O₅

Average Molecular Weight

362.4599

Monoisotopic Molecular Weight

362.20932407

IUPAC Name

3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one

Traditional Name

isohumulone

CAS Registry Number

467-72-1

SMILES

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

InChI Identifier

InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3

InChI Key

QARXXMMQVDCYGZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Vinylogous acid
Tertiary alcohol
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030026)

Source

Exogenous

Food

Food (HMDB: HMDB0030026)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0030026)

Endogenous

Animal

Animal (HMDB: HMDB0030026)

Endogenous (HMDB: HMDB0030026)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030026)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030026)

Lipid metabolism pathway (HMDB: HMDB0030026)

Cellular process

Cell signaling (HMDB: HMDB0030026)

Biochemical process

Lipid transport (HMDB: HMDB0030026)

Role

Biological role

Energy source (HMDB: HMDB0030026)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	62 - 63 °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	0.072 g/L	ALOGPS
logP	2.49	ALOGPS
logP	3.91	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	0.56	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	104.07 m³·mol⁻¹	ChemAxon
Polarizability	39.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	206.544	30932474
DeepCCS	[M-H]-	203.838	30932474
DeepCCS	[M-2H]-	238.478	30932474
DeepCCS	[M+Na]+	213.706	30932474
AllCCS	[M+H]+	188.5	32859911
AllCCS	[M+H-H2O]+	185.9	32859911
AllCCS	[M+NH4]+	191.0	32859911
AllCCS	[M+Na]+	191.7	32859911
AllCCS	[M-H]-	194.3	32859911
AllCCS	[M+Na-2H]-	195.4	32859911
AllCCS	[M+HCOO]-	196.7	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.	8.3 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7943 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2931.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	246.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	149.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	697.7 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	596.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1122.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	558.8 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	1367.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	131.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	180.6 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isohumulone A	CC(C)CC(=O)C1=C(O)C(O)(C(CC=C(C)C)C1=O)C(=O)CC=C(C)C	3794.5	Standard polar	33892256
Isohumulone A	CC(C)CC(=O)C1=C(O)C(O)(C(CC=C(C)C)C1=O)C(=O)CC=C(C)C	2287.7	Standard non polar	33892256
Isohumulone A	CC(C)CC(=O)C1=C(O)C(O)(C(CC=C(C)C)C1=O)C(=O)CC=C(C)C	2253.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isohumulone A,1TMS,isomer #1	CC(C)=CCC(=O)C1(O)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2514.1	Semi standard non polar	33892256
Isohumulone A,1TMS,isomer #2	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2533.8	Semi standard non polar	33892256
Isohumulone A,1TMS,isomer #3	CC(C)=CCC(=O)C1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2464.7	Semi standard non polar	33892256
Isohumulone A,1TMS,isomer #4	CC(C)=CCC(=O)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2587.0	Semi standard non polar	33892256
Isohumulone A,1TMS,isomer #5	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2564.3	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #1	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2578.6	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #10	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2652.6	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #2	CC(C)=CCC(=O)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	2490.2	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #3	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2595.2	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #4	CC(C)=CCC(=O)C1(O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2578.2	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #5	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2547.4	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #6	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2628.1	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #7	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2609.6	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #8	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2545.0	Semi standard non polar	33892256
Isohumulone A,2TMS,isomer #9	CC(C)=CCC(=O)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2582.7	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #1	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	2567.2	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #1	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	2661.2	Standard non polar	33892256
Isohumulone A,3TMS,isomer #10	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2632.4	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #10	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2672.5	Standard non polar	33892256
Isohumulone A,3TMS,isomer #2	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2637.5	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #2	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2656.8	Standard non polar	33892256
Isohumulone A,3TMS,isomer #3	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2611.3	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #3	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2674.9	Standard non polar	33892256
Isohumulone A,3TMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	2565.4	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	2656.0	Standard non polar	33892256
Isohumulone A,3TMS,isomer #5	CC(C)=CCC(=O)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2552.9	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #5	CC(C)=CCC(=O)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2672.0	Standard non polar	33892256
Isohumulone A,3TMS,isomer #6	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2636.6	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #6	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2672.1	Standard non polar	33892256
Isohumulone A,3TMS,isomer #7	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2602.9	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #7	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2662.2	Standard non polar	33892256
Isohumulone A,3TMS,isomer #8	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2613.4	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #8	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2674.7	Standard non polar	33892256
Isohumulone A,3TMS,isomer #9	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2675.2	Semi standard non polar	33892256
Isohumulone A,3TMS,isomer #9	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2674.3	Standard non polar	33892256
Isohumulone A,4TMS,isomer #1	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	2635.6	Semi standard non polar	33892256
Isohumulone A,4TMS,isomer #1	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	2736.7	Standard non polar	33892256
Isohumulone A,4TMS,isomer #2	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2593.9	Semi standard non polar	33892256
Isohumulone A,4TMS,isomer #2	CC(C)=CCC(=O)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2752.9	Standard non polar	33892256
Isohumulone A,4TMS,isomer #3	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2656.7	Semi standard non polar	33892256
Isohumulone A,4TMS,isomer #3	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)C1CC=C(C)C	2774.7	Standard non polar	33892256
Isohumulone A,4TMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2614.2	Semi standard non polar	33892256
Isohumulone A,4TMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2759.9	Standard non polar	33892256
Isohumulone A,4TMS,isomer #5	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2645.8	Semi standard non polar	33892256
Isohumulone A,4TMS,isomer #5	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	2763.7	Standard non polar	33892256
Isohumulone A,5TMS,isomer #1	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2666.6	Semi standard non polar	33892256
Isohumulone A,5TMS,isomer #1	CC(C)=CC=C(O[Si](C)(C)C)C1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	2821.7	Standard non polar	33892256
Isohumulone A,1TBDMS,isomer #1	CC(C)=CCC(=O)C1(O)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2747.7	Semi standard non polar	33892256
Isohumulone A,1TBDMS,isomer #2	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2758.1	Semi standard non polar	33892256
Isohumulone A,1TBDMS,isomer #3	CC(C)=CCC(=O)C1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	2684.9	Semi standard non polar	33892256
Isohumulone A,1TBDMS,isomer #4	CC(C)=CCC(=O)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	2805.8	Semi standard non polar	33892256
Isohumulone A,1TBDMS,isomer #5	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	2796.8	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #1	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	3025.7	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #10	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	3093.6	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #2	CC(C)=CCC(=O)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C	2918.2	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #3	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	3040.4	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #4	CC(C)=CCC(=O)C1(O)C(O[Si](C)(C)C(C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	3025.1	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #5	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	2961.9	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #6	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	3068.2	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #7	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	3045.0	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #8	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	2986.7	Semi standard non polar	33892256
Isohumulone A,2TBDMS,isomer #9	CC(C)=CCC(=O)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3016.7	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #1	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C	3170.2	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #1	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C	3162.2	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #10	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3284.7	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #10	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3210.3	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #2	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	3290.8	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #2	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C	3184.2	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #3	CC(C)=CCC(=O)C1(O[Si](C)(C)C(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)C(=O)C1CC=C(C)C	3252.5	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #3	CC(C)=CCC(=O)C1(O[Si](C)(C)C(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)C(=O)C1CC=C(C)C	3191.8	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C	3221.4	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C	3180.3	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #5	CC(C)=CCC(=O)C1(O)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)=C1O[Si](C)(C)C(C)(C)C	3201.1	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #5	CC(C)=CCC(=O)C1(O)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)=C1O[Si](C)(C)C(C)(C)C	3185.7	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #6	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O[Si](C)(C)C(C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	3303.7	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #6	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)C(O[Si](C)(C)C(C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	3204.6	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #7	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3238.5	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #7	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3187.2	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #8	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3243.5	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #8	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3191.4	Standard non polar	33892256
Isohumulone A,3TBDMS,isomer #9	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	3315.2	Semi standard non polar	33892256
Isohumulone A,3TBDMS,isomer #9	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(=O)C1CC=C(C)C	3213.0	Standard non polar	33892256
Isohumulone A,4TBDMS,isomer #1	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C	3422.8	Semi standard non polar	33892256
Isohumulone A,4TBDMS,isomer #1	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C	3413.4	Standard non polar	33892256
Isohumulone A,4TBDMS,isomer #2	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(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)=C1O[Si](C)(C)C(C)(C)C	3385.6	Semi standard non polar	33892256
Isohumulone A,4TBDMS,isomer #2	CC(C)=CCC(=O)C1(O[Si](C)(C)C(C)(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)=C1O[Si](C)(C)C(C)(C)C	3403.3	Standard non polar	33892256
Isohumulone A,4TBDMS,isomer #3	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(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)C(=O)C1CC=C(C)C	3487.6	Semi standard non polar	33892256
Isohumulone A,4TBDMS,isomer #3	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(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)C(=O)C1CC=C(C)C	3448.6	Standard non polar	33892256
Isohumulone A,4TBDMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)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)=C1O[Si](C)(C)C(C)(C)C	3455.4	Semi standard non polar	33892256
Isohumulone A,4TBDMS,isomer #4	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O)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)=C1O[Si](C)(C)C(C)(C)C	3441.8	Standard non polar	33892256
Isohumulone A,4TBDMS,isomer #5	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3464.4	Semi standard non polar	33892256
Isohumulone A,4TBDMS,isomer #5	CC(C)=CC=C(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3446.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isohumulone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-014s-9484000000-df3d3aa5ac73ff5b3b40	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isohumulone A GC-MS (2 TMS) - 70eV, Positive	splash10-0a4m-7000900000-8ba0d8e95defbd1b3a97	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isohumulone A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isohumulone A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isohumulone A ESI-TOF 10V, Negative-QTOF	splash10-03di-0029000000-822a5c98f0e459a8a3dd	2017-09-12	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 10V, Positive-QTOF	splash10-03di-1029000000-a36c0509d5def9324024	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 20V, Positive-QTOF	splash10-052b-8096000000-0a217511ea67b9e1e650	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 40V, Positive-QTOF	splash10-0a59-9340000000-9e9b9fb4e235c6f18fa9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 10V, Negative-QTOF	splash10-03di-1049000000-39c7238bec6f61470f45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 20V, Negative-QTOF	splash10-002b-9174000000-1c6b3c57c4135dba3508	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 40V, Negative-QTOF	splash10-0a5a-9570000000-7a34e36a8c4ae7aa96d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 10V, Negative-QTOF	splash10-03di-0019000000-f34c609f25950e39070b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 20V, Negative-QTOF	splash10-00o1-0980000000-cf88a0bffaad4cf0eda9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 40V, Negative-QTOF	splash10-0035-7391000000-2808d65271e077cb8086	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 10V, Positive-QTOF	splash10-03di-0029000000-4d4482182444a3433d0b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 20V, Positive-QTOF	splash10-00lr-9121000000-2774e256b43008fe92e5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isohumulone A 40V, Positive-QTOF	splash10-055f-9230000000-999749face84d0005b3f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB001322

KNApSAcK ID

C00050939

Chemspider ID

84039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93090

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Isohumulone A (HMDB0030026)

MOL for HMDB0030026 (Isohumulone A)

3D MOL for HMDB0030026 (Isohumulone A)

3D SDF for HMDB0030026 (Isohumulone A)

3D-SDF for HMDB0030026 (Isohumulone A)

PDB for HMDB0030026 (Isohumulone A)

3D PDB for HMDB0030026 (Isohumulone A)

SMILES for HMDB0030026 (Isohumulone A)

INCHI for HMDB0030026 (Isohumulone A)

Structure for HMDB0030026 (Isohumulone A)

3D Structure for HMDB0030026 (Isohumulone A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra