Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:01 UTC

Update Date

2022-03-07 02:52:26 UTC

HMDB ID

HMDB0030138

Secondary Accession Numbers

HMDB30138

Metabolite Identification

Common Name

Adhumulone

Description

Adhumulone 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. Adhumulone is a bitter tasting compound. Adhumulone has been detected, but not quantified in, several different foods, such as alcoholic beverages, red tea, green tea, teas (Camellia sinensis), and herbal tea. This could make adhumulone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Adhumulone.

Structure

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

  Mrv0541 05061305012D          

 26 26  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.0572    1.7262    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
   -1.4289   -1.6500    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    0.0000    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
    1.4289    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
    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
    2.1434   -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
   -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
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 11  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 19  2  0  0  0  0
 25 20  2  0  0  0  0
 26 21  1  0  0  0  0
M  END

HMDB0030138
     RDKit          3D
Adhumulone
 56 56  0  0  0  0  0  0  0  0999 V2000
   -2.4050    5.1734    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    4.7899    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349    3.3485    0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    2.5223    1.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262    2.8425    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    3.5580    0.5864 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005    1.6097   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3285    0.7847   -1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460    1.1203   -0.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802   -0.4282   -1.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977   -1.4109   -2.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -2.0110   -1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236   -1.9343   -1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.2438   -2.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9525   -2.5450   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2153   -1.0328   -0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -2.1036   -0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433   -0.2268   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -0.4881   -1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -0.5457    0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -1.9622    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800   -2.8538    1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -2.5021    2.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897   -4.2628    1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    1.2050   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057    2.0769   -0.7712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6120    4.9654    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5188    6.2807    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1515    4.6967    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    4.7623    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608    5.4333    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6330    3.3677   -0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    1.6127    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832    2.3282    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257    3.0875    2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946    0.6713   -0.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -0.0879   -2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -1.0531   -3.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008   -2.2764   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095   -2.5146   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123   -1.2725   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004   -0.2289   -2.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149   -1.8261   -3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721   -3.5293   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9639   -2.6392   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407   -1.8583    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    0.3297   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.3849    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139    0.0974    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720   -2.2678   -0.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027   -2.4512    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9325   -1.5462    3.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6342   -3.3068    3.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -4.5910    2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857   -4.3429    0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0322   -4.9360    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 18 25  1  0
 25 26  2  0
 25  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

  Mrv0541 05061305012D          

 26 26  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.0572    1.7262    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
   -1.4289   -1.6500    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    0.0000    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
    1.4289    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
    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
    2.1434   -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
   -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
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 11  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 19  2  0  0  0  0
 25 20  2  0  0  0  0
 26 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030138

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-7-14(6)17(22)16-18(23)15(9-8-12(2)3)19(24)21(26,20(16)25)11-10-13(4)5/h8,10,14-15,23,26H,7,9,11H2,1-6H3

> <INCHI_KEY>
VISQWZWNDCYFMY-UHFFFAOYSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.4599

> <EXACT_MASS>
362.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.577155693440325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
4.521685549

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.786159902247327

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.382654884346379

> <JCHEM_PKA_STRONGEST_BASIC>
-4.458660076505056

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
104.30619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.85e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030138
     RDKit          3D
Adhumulone
 56 56  0  0  0  0  0  0  0  0999 V2000
   -2.4050    5.1734    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    4.7899    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349    3.3485    0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    2.5223    1.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262    2.8425    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    3.5580    0.5864 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005    1.6097   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3285    0.7847   -1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460    1.1203   -0.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802   -0.4282   -1.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977   -1.4109   -2.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -2.0110   -1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236   -1.9343   -1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.2438   -2.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9525   -2.5450   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2153   -1.0328   -0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -2.1036   -0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433   -0.2268   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -0.4881   -1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -0.5457    0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -1.9622    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800   -2.8538    1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -2.5021    2.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897   -4.2628    1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    1.2050   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057    2.0769   -0.7712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6120    4.9654    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5188    6.2807    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1515    4.6967    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    4.7623    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608    5.4333    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6330    3.3677   -0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    1.6127    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832    2.3282    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257    3.0875    2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946    0.6713   -0.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -0.0879   -2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -1.0531   -3.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008   -2.2764   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095   -2.5146   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123   -1.2725   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004   -0.2289   -2.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149   -1.8261   -3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721   -3.5293   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9639   -2.6392   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407   -1.8583    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    0.3297   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.3849    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139    0.0974    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720   -2.2678   -0.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027   -2.4512    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9325   -1.5462    3.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6342   -3.3068    3.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -4.5910    2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857   -4.3429    0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0322   -4.9360    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 18 25  1  0
 25 26  2  0
 25  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.347   4.135   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.303   5.849   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.840   3.222   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.830   4.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   13                                                            
CONECT    6   14                                                            
CONECT    7    1   14                                                       
CONECT    8    9   12                                                       
CONECT    9    8   15                                                       
CONECT   10   11   13                                                       
CONECT   11   10   21                                                       
CONECT   12    2    3    8                                                  
CONECT   13    4    5   10                                                  
CONECT   14    6    7   17                                                  
CONECT   15    9   18   19                                                  
CONECT   16   17   18   20                                                  
CONECT   17   14   16   22                                                  
CONECT   18   15   16   23                                                  
CONECT   19   15   21   24                                                  
CONECT   20   16   21   25                                                  
CONECT   21   11   19   20   26                                             
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   21                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0030138
HETATM    1  C1  UNL     1      -2.405   5.173   1.289  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.983   4.790   0.954  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.035   3.349   0.401  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.628   2.522   1.544  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.326   2.843   0.161  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.270   3.558   0.586  1.00  0.00           O  
HETATM    7  C6  UNL     1       0.600   1.610  -0.507  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.329   0.785  -1.030  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.646   1.120  -0.933  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.180  -0.428  -1.672  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.798  -1.411  -2.165  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.714  -2.011  -1.200  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.024  -1.934  -1.392  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.612  -1.244  -2.584  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.953  -2.545  -0.404  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.215  -1.033  -0.775  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.057  -2.104  -0.237  1.00  0.00           O  
HETATM   18  C15 UNL     1       2.443  -0.227  -0.595  1.00  0.00           C  
HETATM   19  O4  UNL     1       3.296  -0.488  -1.688  1.00  0.00           O  
HETATM   20  C16 UNL     1       3.217  -0.546   0.645  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.654  -1.962   0.659  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.380  -2.854   1.578  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.555  -2.502   2.761  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.890  -4.263   1.464  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.028   1.205  -0.632  1.00  0.00           C  
HETATM   26  O5  UNL     1       2.906   2.077  -0.771  1.00  0.00           O  
HETATM   27  H1  UNL     1      -2.612   4.965   2.346  1.00  0.00           H  
HETATM   28  H2  UNL     1      -2.519   6.281   1.106  1.00  0.00           H  
HETATM   29  H3  UNL     1      -3.151   4.697   0.627  1.00  0.00           H  
HETATM   30  H4  UNL     1      -0.311   4.762   1.814  1.00  0.00           H  
HETATM   31  H5  UNL     1      -0.561   5.433   0.176  1.00  0.00           H  
HETATM   32  H6  UNL     1      -1.633   3.368  -0.497  1.00  0.00           H  
HETATM   33  H7  UNL     1      -1.011   1.613   1.643  1.00  0.00           H  
HETATM   34  H8  UNL     1      -2.683   2.328   1.265  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.626   3.088   2.505  1.00  0.00           H  
HETATM   36  H10 UNL     1      -2.395   0.671  -0.477  1.00  0.00           H  
HETATM   37  H11 UNL     1       0.782  -0.088  -2.578  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.368  -1.053  -3.074  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.201  -2.276  -2.596  1.00  0.00           H  
HETATM   40  H14 UNL     1      -1.310  -2.515  -0.331  1.00  0.00           H  
HETATM   41  H15 UNL     1      -4.712  -1.272  -2.567  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.200  -0.229  -2.735  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.315  -1.826  -3.505  1.00  0.00           H  
HETATM   44  H18 UNL     1      -3.572  -3.529  -0.063  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.964  -2.639  -0.834  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.041  -1.858   0.474  1.00  0.00           H  
HETATM   47  H21 UNL     1       3.409   0.330  -2.207  1.00  0.00           H  
HETATM   48  H22 UNL     1       2.577  -0.385   1.562  1.00  0.00           H  
HETATM   49  H23 UNL     1       4.114   0.097   0.754  1.00  0.00           H  
HETATM   50  H24 UNL     1       4.272  -2.268  -0.204  1.00  0.00           H  
HETATM   51  H25 UNL     1       1.503  -2.451   2.438  1.00  0.00           H  
HETATM   52  H26 UNL     1       2.933  -1.546   3.190  1.00  0.00           H  
HETATM   53  H27 UNL     1       2.634  -3.307   3.537  1.00  0.00           H  
HETATM   54  H28 UNL     1       4.351  -4.591   2.437  1.00  0.00           H  
HETATM   55  H29 UNL     1       4.686  -4.343   0.686  1.00  0.00           H  
HETATM   56  H30 UNL     1       3.032  -4.936   1.269  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4    5   32
CONECT    4   33   34   35
CONECT    5    6    6    7
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   36
CONECT   10   11   16   37
CONECT   11   12   38   39
CONECT   12   13   13   40
CONECT   13   14   15
CONECT   14   41   42   43
CONECT   15   44   45   46
CONECT   16   17   17   18
CONECT   18   19   20   25
CONECT   19   47
CONECT   20   21   48   49
CONECT   21   22   22   50
CONECT   22   23   24
CONECT   23   51   52   53
CONECT   24   54   55   56
CONECT   25   26   26
END

HMDB0030138
     RDKit          3D
Adhumulone
 56 56  0  0  0  0  0  0  0  0999 V2000
   -2.4050    5.1734    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    4.7899    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0349    3.3485    0.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285    2.5223    1.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262    2.8425    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    3.5580    0.5864 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005    1.6097   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3285    0.7847   -1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460    1.1203   -0.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802   -0.4282   -1.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977   -1.4109   -2.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143   -2.0110   -1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236   -1.9343   -1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6115   -1.2438   -2.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9525   -2.5450   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2153   -1.0328   -0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -2.1036   -0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433   -0.2268   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -0.4881   -1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -0.5457    0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -1.9622    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800   -2.8538    1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -2.5021    2.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897   -4.2628    1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281    1.2050   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9057    2.0769   -0.7712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6120    4.9654    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5188    6.2807    1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1515    4.6967    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    4.7623    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5608    5.4333    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6330    3.3677   -0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    1.6127    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832    2.3282    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257    3.0875    2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946    0.6713   -0.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -0.0879   -2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -1.0531   -3.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008   -2.2764   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095   -2.5146   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123   -1.2725   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004   -0.2289   -2.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149   -1.8261   -3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721   -3.5293   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9639   -2.6392   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407   -1.8583    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    0.3297   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.3849    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139    0.0974    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720   -2.2678   -0.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027   -2.4512    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9325   -1.5462    3.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6342   -3.3068    3.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -4.5910    2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857   -4.3429    0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0322   -4.9360    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 18 25  1  0
 25 26  2  0
 25  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₅

Average Molecular Weight

362.4599

Monoisotopic Molecular Weight

362.20932407

IUPAC Name

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

Traditional Name

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

CAS Registry Number

28374-89-2

SMILES

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

InChI Identifier

InChI=1S/C21H30O5/c1-7-14(6)17(22)16-18(23)15(9-8-12(2)3)19(24)21(26,20(16)25)11-10-13(4)5/h8,10,14-15,23,26H,7,9,11H2,1-6H3

InChI Key

VISQWZWNDCYFMY-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
Acyloin
Vinylogous acid
Tertiary alcohol
Enol
Organic oxide
Hydrocarbon derivative
Alcohol
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: HMDB0030138)
Cell membrane (HMDB: HMDB0030138)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030138)

Source

Endogenous

Endogenous (HMDB: HMDB0030138)

Plant

Plant (HMDB: HMDB0030138)

Exogenous

Food

Food (HMDB: HMDB0030138)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Tea

Exogenous (HMDB: HMDB0030138)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	514.35 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.22 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.087 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.068 g/L	ALOGPS
logP	2.58	ALOGPS
logP	4.52	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	-4.5	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	7	ChemAxon
Refractivity	104.31 m³·mol⁻¹	ChemAxon
Polarizability	40.58 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]+	196.911	30932474
DeepCCS	[M-H]-	194.109	30932474
DeepCCS	[M-2H]-	228.844	30932474
DeepCCS	[M+Na]+	204.417	30932474
AllCCS	[M+H]+	188.3	32859911
AllCCS	[M+H-H2O]+	185.6	32859911
AllCCS	[M+NH4]+	190.8	32859911
AllCCS	[M+Na]+	191.5	32859911
AllCCS	[M-H]-	193.8	32859911
AllCCS	[M+Na-2H]-	194.8	32859911
AllCCS	[M+HCOO]-	196.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adhumulone	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	3542.7	Standard polar	33892256
Adhumulone	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	2242.9	Standard non polar	33892256
Adhumulone	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	2233.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adhumulone,1TMS,isomer #1	CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	2482.1	Semi standard non polar	33892256
Adhumulone,1TMS,isomer #2	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2458.2	Semi standard non polar	33892256
Adhumulone,1TMS,isomer #3	CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	2538.8	Semi standard non polar	33892256
Adhumulone,1TMS,isomer #4	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O	2443.9	Semi standard non polar	33892256
Adhumulone,2TMS,isomer #1	CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2556.1	Semi standard non polar	33892256
Adhumulone,2TMS,isomer #2	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	2593.4	Semi standard non polar	33892256
Adhumulone,2TMS,isomer #3	CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O	2501.4	Semi standard non polar	33892256
Adhumulone,2TMS,isomer #4	CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2576.5	Semi standard non polar	33892256
Adhumulone,2TMS,isomer #5	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2518.8	Semi standard non polar	33892256
Adhumulone,2TMS,isomer #6	CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O	2549.8	Semi standard non polar	33892256
Adhumulone,3TMS,isomer #1	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2642.6	Semi standard non polar	33892256
Adhumulone,3TMS,isomer #1	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2600.3	Standard non polar	33892256
Adhumulone,3TMS,isomer #2	CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2536.7	Semi standard non polar	33892256
Adhumulone,3TMS,isomer #2	CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2531.8	Standard non polar	33892256
Adhumulone,3TMS,isomer #3	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O	2582.3	Semi standard non polar	33892256
Adhumulone,3TMS,isomer #3	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O	2525.1	Standard non polar	33892256
Adhumulone,3TMS,isomer #4	CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2612.8	Semi standard non polar	33892256
Adhumulone,3TMS,isomer #4	CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2597.6	Standard non polar	33892256
Adhumulone,4TMS,isomer #1	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2617.8	Semi standard non polar	33892256
Adhumulone,4TMS,isomer #1	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O	2636.8	Standard non polar	33892256
Adhumulone,1TBDMS,isomer #1	CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	2728.2	Semi standard non polar	33892256
Adhumulone,1TBDMS,isomer #2	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	2706.7	Semi standard non polar	33892256
Adhumulone,1TBDMS,isomer #3	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	2781.7	Semi standard non polar	33892256
Adhumulone,1TBDMS,isomer #4	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O	2707.9	Semi standard non polar	33892256
Adhumulone,2TBDMS,isomer #1	CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	2994.9	Semi standard non polar	33892256
Adhumulone,2TBDMS,isomer #2	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O	3051.1	Semi standard non polar	33892256
Adhumulone,2TBDMS,isomer #3	CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O	2974.0	Semi standard non polar	33892256
Adhumulone,2TBDMS,isomer #4	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3030.0	Semi standard non polar	33892256
Adhumulone,2TBDMS,isomer #5	CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	2984.8	Semi standard non polar	33892256
Adhumulone,2TBDMS,isomer #6	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O	3020.2	Semi standard non polar	33892256
Adhumulone,3TBDMS,isomer #1	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3292.6	Semi standard non polar	33892256
Adhumulone,3TBDMS,isomer #1	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3138.1	Standard non polar	33892256
Adhumulone,3TBDMS,isomer #2	CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3204.7	Semi standard non polar	33892256
Adhumulone,3TBDMS,isomer #2	CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3052.7	Standard non polar	33892256
Adhumulone,3TBDMS,isomer #3	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O	3245.7	Semi standard non polar	33892256
Adhumulone,3TBDMS,isomer #3	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O	3035.6	Standard non polar	33892256
Adhumulone,3TBDMS,isomer #4	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3258.9	Semi standard non polar	33892256
Adhumulone,3TBDMS,isomer #4	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3132.7	Standard non polar	33892256
Adhumulone,4TBDMS,isomer #1	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3441.1	Semi standard non polar	33892256
Adhumulone,4TBDMS,isomer #1	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O	3268.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Adhumulone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052n-5597000000-982154af1d40cda1c66a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adhumulone GC-MS (2 TMS) - 70eV, Positive	splash10-0006-5221900000-8d7c8a85db2f88cd5ff2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adhumulone 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 - Adhumulone 10V, Positive-QTOF	splash10-03di-2019000000-2aa507d821fc7ffbdf04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 20V, Positive-QTOF	splash10-0ap1-8059000000-a61f9ba0afd3d2edc74e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 40V, Positive-QTOF	splash10-05o0-9010000000-8427a5e736604f3ed46a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 10V, Negative-QTOF	splash10-03di-0169000000-0a24450480607a9bb301	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 20V, Negative-QTOF	splash10-004i-4293000000-1934c0234b620a011f0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 40V, Negative-QTOF	splash10-0092-9662000000-78a90e3f9bbd37286eb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 10V, Negative-QTOF	splash10-03di-0019000000-e97810a92d4148f645b8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 20V, Negative-QTOF	splash10-03di-0359000000-a53af1b57ba359cce8a2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 40V, Negative-QTOF	splash10-004i-7932000000-cb58dcffcbfa7664f791	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 10V, Positive-QTOF	splash10-03di-0009000000-7680edf2c7b3883c08d3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 20V, Positive-QTOF	splash10-03di-2669000000-888dea72aeb40f693d80	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adhumulone 40V, Positive-QTOF	splash10-053r-9341000000-08c28f74f14d434ada9b	2021-09-25	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

FDB001943

KNApSAcK ID

C00035518

Chemspider ID

19992469

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1679571

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Adhumulone (HMDB0030138)

MOL for HMDB0030138 (Adhumulone)

3D MOL for HMDB0030138 (Adhumulone)

3D SDF for HMDB0030138 (Adhumulone)

3D-SDF for HMDB0030138 (Adhumulone)

PDB for HMDB0030138 (Adhumulone)

3D PDB for HMDB0030138 (Adhumulone)

SMILES for HMDB0030138 (Adhumulone)

INCHI for HMDB0030138 (Adhumulone)

Structure for HMDB0030138 (Adhumulone)

3D Structure for HMDB0030138 (Adhumulone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra