NP-MRD: Showing NP-Card for Humulone (NP0051545)

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Record Information

Version

2.0

Created at

2022-04-27 22:52:16 UTC

Updated at

2022-04-27 22:52:16 UTC

NP-MRD ID

NP0051545

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Humulone

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). Humulone is found in Humulus lupulus . Humulone was first documented in 1949 (PMID: 16695762). An optically active cyclic ketone consisting of 3,5,6-trihydroxycyclohexa-2,4-dien-1-one bearing two 3-methylbut-2-en-1-yl substituents at positions 4 and 6 as well as a 3-methylbutanoyl group at the 2-position (PMID: 10631313) (PMID: 14920156) (PMID: 14948476) (PMID: 17372274).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652301212022273D          

 26 26  0  0  0  0            999 V2000
   -3.4960    3.2569   -0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    4.8354   -1.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -2.9510    1.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6458   -2.5089    2.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327    0.9053   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.3500    0.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519    3.0921   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2132    1.9663    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7058   -2.9305    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2428   -2.7916    0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    0.3462   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127    3.6863   -1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966   -2.8024    1.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2996   -0.2395   -0.3661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5633    0.6942    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9504   -0.7626   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5096   -0.5860   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877    0.5279   -0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047   -0.3775   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802   -1.7503   -0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775   -1.6700   -0.6549 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3889   -1.9104   -0.8249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    1.6492    0.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6803   -0.2451   -0.1366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -2.8543   -0.9959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -2.0612   -1.9313 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  3  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  3  0  0  0
 10 21  1  0  0  0  0
 11 14  1  0  0  0  0
 11 16  1  0  0  0  0
 15 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 17  1  0  0  0  0
 16 22  2  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 18 23  1  0  0  0  0
 19 21  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 21 26  1  6  0  0  0
M  END

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
   -4.6295   -3.0861   -1.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5359   -2.6007   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753   -4.1253    0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4791   -2.1428    0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.5413   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286   -0.0515   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469    0.9638    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943    1.8407    1.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    1.3600    1.0135 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4375    1.4802    2.3246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    2.8152    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6244    3.6121    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963    4.2794    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890    5.0337    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086    4.4988   -1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    0.6026    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554    1.0979    0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322   -0.7403   -0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1574   -1.5837   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657   -2.4639   -1.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385   -1.4685    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6354   -1.9801   -0.5368 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8194   -1.2299   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8475   -1.5894    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959   -0.9410   -0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5374   -2.0330   -1.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8880   -2.4166   -2.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5188   -4.0927   -1.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5641   -3.1730   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6356   -3.7902    1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4564   -3.9283    0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3098   -4.7994   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -2.4352    0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819   -0.1973    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8411   -0.5621   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823    1.8200    2.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604    0.6012    2.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908    3.2011    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1648    2.7236   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835    3.5847    2.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1160    4.2442    1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704    5.8157    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107    5.4286    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    3.6417   -1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355    4.5635   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    5.4958   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3056   -2.3237    1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5532   -0.5641    0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778   -3.0574   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6242   -1.9161   -2.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1929   -0.3355   -1.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8894   -0.9201   -1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6714   -2.2053    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7955   -0.5250    0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7340   -1.9321   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1524   -2.9528   -1.1779 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  1
  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  6
 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


  Mrv1652301212022273D          

 26 26  0  0  0  0            999 V2000
   -3.4960    3.2569   -0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    4.8354   -1.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -2.9510    1.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6458   -2.5089    2.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327    0.9053   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.3500    0.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519    3.0921   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2132    1.9663    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7058   -2.9305    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2428   -2.7916    0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    0.3462   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127    3.6863   -1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966   -2.8024    1.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2996   -0.2395   -0.3661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5633    0.6942    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9504   -0.7626   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5096   -0.5860   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877    0.5279   -0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047   -0.3775   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802   -1.7503   -0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775   -1.6700   -0.6549 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3889   -1.9104   -0.8249 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    1.6492    0.2110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6803   -0.2451   -0.1366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -2.8543   -0.9959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -2.0612   -1.9313 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  3  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  3  0  0  0
 10 21  1  0  0  0  0
 11 14  1  0  0  0  0
 11 16  1  0  0  0  0
 15 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 17  1  0  0  0  0
 16 22  2  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 18 23  1  0  0  0  0
 19 21  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 21 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051545

> <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/t21-/m1/s1

> <INCHI_KEY>
VMSLCPKYRPDHLN-OAQYLSRUSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.466

> <EXACT_MASS>
362.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.35017828863901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-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>
94.83

> <JCHEM_REFRACTIVITY>
106.30349999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
humulone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0      -3.496   3.257  -0.714  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.902   4.835  -1.950  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.880  -2.951   1.450  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.646  -2.509   2.719  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.233   0.905  -0.071  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.395  -1.350   0.655  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.052   3.092  -0.492  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.213   1.966   0.422  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.706  -2.930   0.325  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.243  -2.792   0.284  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.866   0.346  -0.205  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.113   3.686  -1.016  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.397  -2.802   1.454  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.300  -0.240  -0.366  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.563   0.694   0.018  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.950  -0.763  -0.491  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.510  -0.586  -0.399  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.888   0.528  -0.074  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.305  -0.378  -0.251  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.680  -1.750  -0.696  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.778  -1.670  -0.655  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.389  -1.910  -0.825  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.656   1.649   0.211  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.680  -0.245  -0.137  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.227  -2.854  -0.996  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.246  -2.061  -1.931  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    8   12                                                       
CONECT    8    7   15                                                       
CONECT    9   10   13                                                       
CONECT   10    9   21                                                       
CONECT   11   14   16                                                       
CONECT   12    1    2    7                                                  
CONECT   13    3    4    9                                                  
CONECT   14    5    6   11                                                  
CONECT   15    8   18   19                                                  
CONECT   16   11   17   22                                                  
CONECT   17   16   18   20                                                  
CONECT   18   15   17   23                                                  
CONECT   19   15   21   24                                                  
CONECT   20   17   21   25                                                  
CONECT   21   10   19   20   26                                             
CONECT   22   16                                                            
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

View in JSmol

Synonyms

Value	Source
(6R)-3,5,6-Trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone	ChEBI
alpha-Humulon	ChEBI
Humulon	ChEBI
a-Humulon	Generator
Α-humulon	Generator
3,5,6-Trihydroxy-4-isovaleryl-2,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadiene-1-one	MeSH
alpha Bitter acid	MeSH
Humulone	MeSH

Chemical Formula

C₂₁H₃₀O₅

Average Mass

362.4660 Da

Monoisotopic Mass

362.20932 Da

IUPAC Name

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

Traditional Name

humulone

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/t21-/m1/s1

InChI Key

VMSLCPKYRPDHLN-OAQYLSRUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

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

cyclic ketone (CHEBI:5769 )
aromatic ketone (CHEBI:5769 )
triol (CHEBI:5769 )
diketone (CHEBI:5769 )
Phloroglucinols (C10695 )

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	40.35 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

C00002697

Chemspider ID

Not Available

KEGG Compound ID

C10695

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Humulone

METLIN ID

Not Available

PubChem Compound

442911

PDB ID

Not Available

ChEBI ID

5769

Good Scents ID

Not Available

References

General References

Yamamoto K, Wang J, Yamamoto S, Tobe H: Suppression of cyclooxygenase-2 gene transcription by humulon of beer hop extract studied with reference to glucocorticoid. FEBS Lett. 2000 Jan 14;465(2-3):103-6. doi: 10.1016/s0014-5793(99)01727-5. [PubMed:10631313 ]
ERDMANN WF: [Phytoncides. I. Lupulone and humulone; their antibacterial action and their use in tuberculous infections]. Pharmazie. 1951 Sep;6(9):442-51. [PubMed:14920156 ]
ERDMANN WF: [Lupulon and humulon, their antibacterial effects and therapeutic use in tuberculous infections]. Pharmazie. 1952 Feb;7(2):75-86. [PubMed:14948476 ]
Lewis JC, Alderton G, Carson JF, Reynolds DM, Maclay WD: LUPULON AND HUMULON-ANTIBIOTIC CONSTITUENTS OF HOPS. J Clin Invest. 1949 Sep;28(5 Pt 1):916-9. doi: 10.1172/JCI102178. [PubMed:16695762 ]
Lee JC, Kundu JK, Hwang DM, Na HK, Surh YJ: Humulone inhibits phorbol ester-induced COX-2 expression in mouse skin by blocking activation of NF-kappaB and AP-1: IkappaB kinase and c-Jun-N-terminal kinase as respective potential upstream targets. Carcinogenesis. 2007 Jul;28(7):1491-8. doi: 10.1093/carcin/bgm054. Epub 2007 Mar 19. [PubMed:17372274 ]

Showing NP-Card for Humulone (NP0051545)

MOL for NP0051545 (Humulone)

3D MOL for NP0051545 (Humulone)

3D SDF for NP0051545 (Humulone)

3D-SDF for NP0051545 (Humulone)

PDB for NP0051545 (Humulone)

3D PDB for NP0051545 (Humulone)

SMILES for NP0051545 (Humulone)

INCHI for NP0051545 (Humulone)

Structure for NP0051545 (Humulone)

3D Structure for NP0051545 (Humulone)