NP-MRD: Showing NP-Card for beta-Bitter acid (NP0051548)

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Record Information

Version

2.0

Created at

2022-04-27 22:52:21 UTC

Updated at

2022-04-27 22:52:21 UTC

NP-MRD ID

NP0051548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Bitter acid

Description

3,5-Dihydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. beta-Bitter acid is found in hops, Humulus japonicus and Humulus lupulus . Based on a literature review very few articles have been published on 3,5-dihydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200522D          

 30 30  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847    2.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    3.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    2.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1381    2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764    3.4228    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
    0.7145   -1.2375    0.0000 O   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
    2.1434   -1.2375    0.0000 O   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  3 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END

     RDKit          3D

 68 68  0  0  0  0  0  0  0  0999 V2000
   -1.0962    5.6823    1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7861    5.2609   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0996    6.1224   -0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2738    4.1490   -0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    3.2507    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5242    1.8942    0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2147    0.8886   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5019    1.1443   -0.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425   -0.4766   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5035   -1.5182   -0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6524   -1.2328   -1.2287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0991   -2.9145   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -3.8182   -1.4277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4544   -3.7675   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -5.2216   -1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4298   -0.6942    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -2.0204    0.1284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094    0.3497    0.6419 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6119    0.6441   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344   -0.4996   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5313   -0.8453   -2.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.0844   -3.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3660   -2.0027   -2.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007    0.0889    2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -1.1330    2.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544   -1.0841    2.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290   -2.3362    3.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    0.2097    3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2147    1.6774    0.7454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132    2.5963    1.3125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150    5.6235    1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6660    4.9657    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631    6.7285    1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3613    7.1063   -1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772    5.6471   -1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    6.2577   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0071    3.8891   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748    3.5982    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949    3.2111   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2584    0.9397   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681   -3.2787    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2187   -3.0620   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -3.4777   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8663   -4.7944   -0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450   -3.2984    0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2493   -3.1864   -1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1635   -5.8516   -2.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015   -5.5986   -0.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5568   -5.1539   -1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7888   -2.3439   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951    1.1163   -1.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    1.4748    0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9584   -1.0495    0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.0405   -2.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062   -0.4519   -4.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    0.9635   -3.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596   -1.9285   -3.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8482   -2.9857   -2.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -2.0155   -1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1100    0.1483    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6560    0.9726    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3374   -2.1074    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308   -2.3558    2.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708   -3.2034    2.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422   -2.4005    4.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9320    0.8209    3.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5051    0.0176    3.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7965    0.7939    2.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  6
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 18 29  1  0
 29 30  2  0
 29  6  1  0
  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
 14 44  1  0
 14 45  1  0
 14 46  1  0
 13 43  1  6
 15 47  1  0
 15 48  1  0
 15 49  1  0
 12 41  1  0
 12 42  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
  5 38  1  0
  5 39  1  0
  4 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  8 40  1  0
M  END


  Mrv1652304282200522D          

 30 30  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847    2.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    3.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    2.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1381    2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764    3.4228    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
    0.7145   -1.2375    0.0000 O   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
    2.1434   -1.2375    0.0000 O   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  3 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O

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

> <INCHI_KEY>
WPVSVIXDXMNGGN-UHFFFAOYSA-N

> <FORMULA>
C26H38O4

> <MOLECULAR_WEIGHT>
414.586

> <EXACT_MASS>
414.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.08562074274104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
6.119193200999999

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.06582474964458

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.454855561621957

> <JCHEM_PKA_STRONGEST_BASIC>
-5.148134345312969

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
128.60609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
B'' -acid

> <JCHEM_VEBER_RULE>
0

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HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.928   3.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.651   5.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.190   5.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.835   6.389   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.596   3.723   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.319   5.083   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.858   5.137   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.503   6.389   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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    7   30                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1    8   13                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    4   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    3                                                            
CONECT   24    2   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    1                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₄

Average Mass

414.5860 Da

Monoisotopic Mass

414.27701 Da

IUPAC Name

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

Traditional Name

B'' -acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O

InChI Identifier

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

InChI Key

WPVSVIXDXMNGGN-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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	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	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	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	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	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	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	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	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	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	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	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	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	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	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	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	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	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	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
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
hops	-	KNApSAcK
Humulus japonicus	Plant	KNApSAcK
Humulus lupulus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous acids

Sub Class

Not Available

Direct Parent

Vinylogous acids

Alternative Parents

Substituents

Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

polyol (CHEBI:6574 )
Phloroglucinols (C10706 )

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	4.33	ALOGPS
logP	6.12	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.61 m³·mol⁻¹	ChemAxon
Polarizability	48.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002701

Chemspider ID

13433819

KEGG Compound ID

C10706

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

Good Scents ID

rw1039101

References

General References

Not Available

Showing NP-Card for beta-Bitter acid (NP0051548)

MOL for NP0051548 (beta-Bitter acid)

3D MOL for NP0051548 (beta-Bitter acid)

3D SDF for NP0051548 (beta-Bitter acid)

3D-SDF for NP0051548 (beta-Bitter acid)

PDB for NP0051548 (beta-Bitter acid)

3D PDB for NP0051548 (beta-Bitter acid)

SMILES for NP0051548 (beta-Bitter acid)

INCHI for NP0051548 (beta-Bitter acid)

Structure for NP0051548 (beta-Bitter acid)

3D Structure for NP0051548 (beta-Bitter acid)