NP-MRD: Showing NP-Card for 3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one (NP0209997)

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Record Information

Version

2.0

Created at

2022-09-05 07:38:02 UTC

Updated at

2022-09-05 07:38:02 UTC

NP-MRD ID

NP0209997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one

Description

Humulone, also known as alpha bitter acid, belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Humulone is an extremely weak basic (essentially neutral) compound (based on its pKa). This conversion yields the benzenoid 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one. Two side-chains are prenyl groups and one is an isovaleryl group. Antimicrobial properties of humulone are antiviral and antibacterial. These “alpha acids” survive the boiling process, although numerous oxidized derivatives are produced. During the brewing process, humulone degrades to cis- and trans-isohumulone. In terms of structure, humulone is a phloroglucinol derivative with three isoprenoid side-chains. Humulone (α-lupulic acid), a vinylogous type of organic acid, is a bitter-tasting chemical compound found in the resin of mature hops (Humulus lupulus). As determined by INADEQUATE 2D NMR, the biosynthesis of humulone in Humulus lupulus starts with an isovaleryl-CoA unit and 3 malonyl-CoA units catalyzed by phlorovalerophenone synthase. This step is followed by prenylation with 1-bromo-3-methyl-2-butene to give humulone. 3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one is found in Humulus lupulus. Humulone can be synthesized by the acylation of 1,2,3,5-benzenetetrol with isovaleryl chloride to give 2,3,4,6-tetrahydroxyisovalerophenone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512432D          

 26 26  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.8250    0.0000 C   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 C   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
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    4.0520    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
    1.4289    0.8250    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
    1.2154    5.1749    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1377    4.8826   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322    5.8261   -1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    3.7912    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869    2.8500    1.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186    1.4612    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2173    0.9830    0.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745    1.8325    0.8742 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5487   -0.3721    0.0698 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4619   -0.2147   -0.9931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -1.0171    1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -2.3949    0.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0006   -2.7513    0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0295   -1.7229    1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3452   -4.1384    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691   -1.1316   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101   -2.2821   -0.8847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151   -0.6439   -0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232   -1.5090   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -2.6828   -0.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205   -1.1034   -0.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4766   -2.2433   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3095   -2.8028   -2.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4276   -3.3140    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1351    0.5971    0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    1.1282    0.4307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2051    5.2259    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199    4.3907   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    6.1530   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    6.5587   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683    6.3334   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447    5.2658   -1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7606    3.6470   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817    3.2477    1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    2.8046    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    2.1849    0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115   -0.5921   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641   -1.0430    2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2337   -0.4280    1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714   -3.1627    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331   -1.3907    2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0289   -2.1952    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8760   -0.8728    0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445   -4.1666   -0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -4.8038    0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2583   -4.4826    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7570   -0.7585    0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7359   -0.3473   -1.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5109   -1.7929   -0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343   -3.7756   -2.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3107   -3.0809   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8792   -2.0888   -2.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5399   -3.9340    0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3887   -3.8992    0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802   -2.7982    1.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208    1.5988   -0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 24  1  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 25  2  0
 25 26  1  0
 25  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 22 49  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 21 47  1  0
 21 48  1  0
 26 56  1  0
  5 34  1  0
  5 35  1  0
  4 33  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
  8 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
M  END


  Mrv1533004171512432D          

 26 26  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.8250    0.0000 C   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 C   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
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    4.0520    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
    1.4289    0.8250    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209997

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
VMSLCPKYRPDHLN-UHFFFAOYSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.466

> <EXACT_MASS>
362.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.272449689277124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
3.6006081660000016

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.243300276254771

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.129538359024711

> <JCHEM_PKA_STRONGEST_BASIC>
-4.243042789896745

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
106.30349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.787   6.117   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.260   7.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.303   5.849   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  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13    7   21                                                  
CONECT   21   20                                                            
CONECT   22   10   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
3,5,6-Trihydroxy-4-isovaleryl-2,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadiene-1-one	MeSH
alpha Bitter acid	MeSH
Humulon	MeSH
Humulone	MeSH

Chemical Formula

C₂₁H₃₀O₅

Average Mass

362.4660 Da

Monoisotopic Mass

362.20932 Da

IUPAC Name

3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one

Traditional Name

3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

VMSLCPKYRPDHLN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Humulus lupulus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Vinylogous acid
Tertiary alcohol
Cyclic ketone
Ketone
Polyol
Enol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.31	ALOGPS
logP	3.6	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.3 m³·mol⁻¹	ChemAxon
Polarizability	40.27 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Humulone

METLIN ID

Not Available

PubChem Compound

549481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one (NP0209997)

MOL for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D MOL for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D SDF for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D-SDF for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

PDB for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D PDB for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

SMILES for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

INCHI for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

Structure for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D Structure for NP0209997 (3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one)