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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:48 UTC

Update Date

2022-03-07 02:52:25 UTC

HMDB ID

HMDB0030103

Secondary Accession Numbers

HMDB30103

Metabolite Identification

Common Name

Hulupone

Description

Hulupone 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. Hulupone has been detected, but not quantified in, alcoholic beverages. This could make hulupone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Hulupone.

Structure

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

HMDB0030103
     RDKit          3D
Hulupone
 52 52  0  0  0  0  0  0  0  0999 V2000
   -2.5301   -3.8245    1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.5891    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874   -2.6184   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -1.4706    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -0.1875    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820    0.3616   -0.7343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163    1.6608   -1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711    2.6603   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5877    3.8209   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    4.0846   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    4.8089    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9503   -0.5537   -1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -0.9662   -2.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949   -0.9130   -1.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2023   -1.8788   -1.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -0.2158   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -0.3146    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3205    0.4311    1.3709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.2484   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3620   -1.0993    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4522   -2.0754    0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9662    0.2656    0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.6761    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911    1.5802    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3640   -4.5756    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -3.6370    2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -4.3174    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -2.2101   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8861   -1.9104   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4476   -3.6266   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361   -1.4921    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5225   -0.2775   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059    0.5448    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690    2.0013   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    1.4908   -2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713    2.4653    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    3.4007   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084    4.0349   -2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    5.1167   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207    4.6734    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    4.5944    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9156    5.8531    0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1263   -2.8364   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8435   -2.3100    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4285   -1.0853   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305   -1.3717    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2505   -2.1066    1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916   -3.0729    0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -1.6508   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9426    0.2929    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    1.0410    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.5761    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 16 23  1  0
 23 24  2  0
 23  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 15 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
M  END


  Mrv0541 05061305002D          

 24 24  0  0  0  0            999 V2000
   -2.1503    1.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2858    1.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  7  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 15  2  0  0  0  0
 22 17  1  0  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030103

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-12(2)7-9-20(10-8-13(3)4)18(23)16(17(22)19(20)24)15(21)11-14(5)6/h7-8,14,22H,9-11H2,1-6H3

> <INCHI_KEY>
YDAFVJGIRJZGKB-UHFFFAOYSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.4339

> <EXACT_MASS>
332.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.486969867116215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-2,2-bis(3-methylbut-2-en-1-yl)-5-(3-methylbutanoyl)cyclopent-4-ene-1,3-dione

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
5.093537212666668

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.289422850466303

> <JCHEM_PKA_STRONGEST_BASIC>
-6.289466445206039

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
98.25759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2,2-bis(3-methylbut-2-en-1-yl)-5-(3-methylbutanoyl)cyclopent-4-ene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030103
     RDKit          3D
Hulupone
 52 52  0  0  0  0  0  0  0  0999 V2000
   -2.5301   -3.8245    1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.5891    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874   -2.6184   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -1.4706    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -0.1875    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820    0.3616   -0.7343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163    1.6608   -1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711    2.6603   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5877    3.8209   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    4.0846   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    4.8089    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9503   -0.5537   -1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -0.9662   -2.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949   -0.9130   -1.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2023   -1.8788   -1.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -0.2158   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -0.3146    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3205    0.4311    1.3709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.2484   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3620   -1.0993    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4522   -2.0754    0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9662    0.2656    0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.6761    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911    1.5802    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3640   -4.5756    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -3.6370    2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -4.3174    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -2.2101   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8861   -1.9104   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4476   -3.6266   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361   -1.4921    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5225   -0.2775   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059    0.5448    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690    2.0013   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    1.4908   -2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713    2.4653    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    3.4007   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084    4.0349   -2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    5.1167   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207    4.6734    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    4.5944    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9156    5.8531    0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1263   -2.8364   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8435   -2.3100    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4285   -1.0853   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305   -1.3717    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2505   -2.1066    1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916   -3.0729    0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -1.6508   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9426    0.2929    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    1.0410    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.5761    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 16 23  1  0
 23 24  2  0
 23  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 15 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.014   3.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.031   5.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.133   3.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.151   5.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -5.595   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.426  -4.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.477   2.904   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.597   2.904   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.507   4.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.627   4.049   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   14                                                            
CONECT    7    9   12                                                       
CONECT    8   10   13                                                       
CONECT    9    7   20                                                       
CONECT   10    8   20                                                       
CONECT   11   14   15                                                       
CONECT   12    1    2    7                                                  
CONECT   13    3    4    8                                                  
CONECT   14    5    6   11                                                  
CONECT   15   11   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   19   22                                                  
CONECT   18   16   20   23                                                  
CONECT   19   17   20   24                                                  
CONECT   20    9   10   18   19                                             
CONECT   21   15                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0030103
HETATM    1  C1  UNL     1      -2.530  -3.824   1.257  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.930  -2.589   0.557  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.087  -2.618  -0.378  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.269  -1.471   0.758  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.601  -0.188   0.098  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.482   0.362  -0.734  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.916   1.661  -1.365  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.271   2.660  -0.328  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.588   3.821  -0.259  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.488   4.085  -1.221  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.959   4.809   0.788  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.950  -0.554  -1.729  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.540  -0.966  -2.753  1.00  0.00           O  
HETATM   14  C13 UNL     1       0.395  -0.913  -1.330  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.202  -1.879  -1.951  1.00  0.00           O  
HETATM   16  C14 UNL     1       0.814  -0.216  -0.278  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.113  -0.315   0.391  1.00  0.00           C  
HETATM   18  O3  UNL     1       2.320   0.431   1.371  1.00  0.00           O  
HETATM   19  C16 UNL     1       3.173  -1.248  -0.041  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.362  -1.099   0.846  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.452  -2.075   0.384  1.00  0.00           C  
HETATM   22  C19 UNL     1       4.966   0.266   0.834  1.00  0.00           C  
HETATM   23  C20 UNL     1      -0.277   0.676   0.085  1.00  0.00           C  
HETATM   24  O4  UNL     1      -0.191   1.580   0.971  1.00  0.00           O  
HETATM   25  H1  UNL     1      -3.364  -4.576   1.297  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.276  -3.637   2.335  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.648  -4.317   0.789  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.697  -2.210  -1.354  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.886  -1.910  -0.069  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.448  -3.627  -0.584  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.436  -1.492   1.443  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.523  -0.277  -0.494  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.806   0.545   0.910  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.069   2.001  -2.001  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.817   1.491  -2.018  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.071   2.465   0.365  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.370   3.401  -1.018  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.808   4.035  -2.272  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.123   5.117  -1.047  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.221   4.673   1.626  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.969   4.594   1.190  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.916   5.853   0.401  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.126  -2.836  -1.632  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.843  -2.310   0.019  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.428  -1.085  -1.113  1.00  0.00           H  
HETATM   46  H22 UNL     1       4.030  -1.372   1.888  1.00  0.00           H  
HETATM   47  H23 UNL     1       6.250  -2.107   1.148  1.00  0.00           H  
HETATM   48  H24 UNL     1       4.992  -3.073   0.220  1.00  0.00           H  
HETATM   49  H25 UNL     1       5.876  -1.651  -0.557  1.00  0.00           H  
HETATM   50  H26 UNL     1       5.943   0.293   0.308  1.00  0.00           H  
HETATM   51  H27 UNL     1       4.338   1.041   0.360  1.00  0.00           H  
HETATM   52  H28 UNL     1       5.163   0.576   1.874  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4    4
CONECT    3   28   29   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7   12   23
CONECT    7    8   34   35
CONECT    8    9    9   36
CONECT    9   10   11
CONECT   10   37   38   39
CONECT   11   40   41   42
CONECT   12   13   13   14
CONECT   14   15   16   16
CONECT   15   43
CONECT   16   17   23
CONECT   17   18   18   19
CONECT   19   20   44   45
CONECT   20   21   22   46
CONECT   21   47   48   49
CONECT   22   50   51   52
CONECT   23   24   24
END

HMDB0030103
     RDKit          3D
Hulupone
 52 52  0  0  0  0  0  0  0  0999 V2000
   -2.5301   -3.8245    1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -2.5891    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874   -2.6184   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -1.4706    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -0.1875    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820    0.3616   -0.7343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163    1.6608   -1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711    2.6603   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5877    3.8209   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    4.0846   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    4.8089    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9503   -0.5537   -1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -0.9662   -2.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949   -0.9130   -1.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2023   -1.8788   -1.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -0.2158   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -0.3146    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3205    0.4311    1.3709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.2484   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3620   -1.0993    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4522   -2.0754    0.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9662    0.2656    0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.6761    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911    1.5802    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3640   -4.5756    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -3.6370    2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -4.3174    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -2.2101   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8861   -1.9104   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4476   -3.6266   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4361   -1.4921    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5225   -0.2775   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059    0.5448    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690    2.0013   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    1.4908   -2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713    2.4653    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    3.4007   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084    4.0349   -2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    5.1167   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207    4.6734    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    4.5944    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9156    5.8531    0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1263   -2.8364   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8435   -2.3100    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4285   -1.0853   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305   -1.3717    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2505   -2.1066    1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916   -3.0729    0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -1.6508   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9426    0.2929    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    1.0410    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.5761    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 16 23  1  0
 23 24  2  0
 23  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 15 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Molecular Weight

332.4339

Monoisotopic Molecular Weight

332.198759384

IUPAC Name

4-hydroxy-2,2-bis(3-methylbut-2-en-1-yl)-5-(3-methylbutanoyl)cyclopent-4-ene-1,3-dione

Traditional Name

4-hydroxy-2,2-bis(3-methylbut-2-en-1-yl)-5-(3-methylbutanoyl)cyclopent-4-ene-1,3-dione

CAS Registry Number

468-62-2

SMILES

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

InChI Identifier

InChI=1S/C20H28O4/c1-12(2)7-9-20(10-8-13(3)4)18(23)16(17(22)19(20)24)15(21)11-14(5)6/h7-8,14,22H,9-11H2,1-6H3

InChI Key

YDAFVJGIRJZGKB-UHFFFAOYSA-N

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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030103)

Cellular substructure

Extracellular (HMDB: HMDB0030103)
Membrane (HMDB: HMDB0030103)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030103)

Source

Endogenous

Endogenous (HMDB: HMDB0030103)

Exogenous

Food

Food (HMDB: HMDB0030103)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0030103)

Role

Biological role

Energy source (HMDB: HMDB0030103)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030103)

Emulsifier (HMDB: HMDB0030103)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18.19 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.18	ALOGPS
logP	5.09	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	98.26 m³·mol⁻¹	ChemAxon
Polarizability	37.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	196.13	30932474
DeepCCS	[M-H]-	193.772	30932474
DeepCCS	[M-2H]-	227.711	30932474
DeepCCS	[M+Na]+	202.938	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	178.0	32859911
AllCCS	[M+NH4]+	183.5	32859911
AllCCS	[M+Na]+	184.2	32859911
AllCCS	[M-H]-	188.4	32859911
AllCCS	[M+Na-2H]-	189.1	32859911
AllCCS	[M+HCOO]-	190.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hulupone	CC(C)CC(=O)C1=C(O)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O	2960.5	Standard polar	33892256
Hulupone	CC(C)CC(=O)C1=C(O)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O	2073.3	Standard non polar	33892256
Hulupone	CC(C)CC(=O)C1=C(O)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O	2151.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hulupone,1TMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C1=O	2347.6	Semi standard non polar	33892256
Hulupone,1TMS,isomer #2	CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C1=O	2399.3	Semi standard non polar	33892256
Hulupone,2TMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C1=O	2409.9	Semi standard non polar	33892256
Hulupone,2TMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C1=O	2389.4	Standard non polar	33892256
Hulupone,1TBDMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C1=O	2579.5	Semi standard non polar	33892256
Hulupone,1TBDMS,isomer #2	CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C1=O	2625.9	Semi standard non polar	33892256
Hulupone,2TBDMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C1=O	2855.9	Semi standard non polar	33892256
Hulupone,2TBDMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C(C)(C)C)C1=O	2785.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hulupone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9175000000-c15a8aa6f2377d559277	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hulupone GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9118000000-e4b7d2c5771a2ab0413d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hulupone 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 - Hulupone 10V, Positive-QTOF	splash10-001i-0279000000-59ab67d920b92120703f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 20V, Positive-QTOF	splash10-05r1-2391000000-8e9fdd59dce46f4d919a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 40V, Positive-QTOF	splash10-0002-7930000000-a6352426373070f6a192	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 10V, Negative-QTOF	splash10-001i-0039000000-4d72af23fe6d4c21ce69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 20V, Negative-QTOF	splash10-000t-4193000000-c0ada589facefaa9dbdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 40V, Negative-QTOF	splash10-0002-9551000000-f58f6296e150e4e21854	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 10V, Positive-QTOF	splash10-001i-0089000000-06062b31343bd8bf21ae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 20V, Positive-QTOF	splash10-0a4l-5392000000-bdeefa0bb68daba0190a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 40V, Positive-QTOF	splash10-0a4u-6930000000-3b52edb8ea51817165f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 10V, Negative-QTOF	splash10-001i-0009000000-bd69facddc36af19b908	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 20V, Negative-QTOF	splash10-003s-0395000000-6202dc236255f0018266	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupone 40V, Negative-QTOF	splash10-004l-2940000000-22e027887af09063f678	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB001901

KNApSAcK ID

C00055780

Chemspider ID

547440

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

630403

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817051

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 Hulupone (HMDB0030103)

MOL for HMDB0030103 (Hulupone)

3D MOL for HMDB0030103 (Hulupone)

3D SDF for HMDB0030103 (Hulupone)

3D-SDF for HMDB0030103 (Hulupone)

PDB for HMDB0030103 (Hulupone)

3D PDB for HMDB0030103 (Hulupone)

SMILES for HMDB0030103 (Hulupone)

INCHI for HMDB0030103 (Hulupone)

Structure for HMDB0030103 (Hulupone)

3D Structure for HMDB0030103 (Hulupone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra