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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:47 UTC

Update Date

2022-03-07 02:52:25 UTC

HMDB ID

HMDB0030102

Secondary Accession Numbers

HMDB30102

Metabolite Identification

Common Name

Hulupinic acid

Description

Hulupinic acid, also known as hulupinate, 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. Hulupinic acid has been detected, but not quantified in, alcoholic beverages. This could make hulupinic acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Hulupinic acid.

Structure

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

HMDB0030102
     RDKit          3D
Hulupinic acid
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.1208   -1.7626    1.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -1.1464    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -1.8110   -0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0887   -0.0420   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.7781    0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    0.9189   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -0.3851   -0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2688   -1.0200    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -1.3549    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1163   -1.9804    1.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4503   -1.1181   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5374    1.6543   -1.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.2216   -2.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458    3.0660   -1.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    4.1289   -1.8128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5197    3.2164   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432    4.4050    0.2105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1135    1.9179   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.7639    0.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830   -2.3090    2.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -1.0525    2.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -2.5172    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891   -2.7849   -0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845   -1.2414   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5684   -2.0592    0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176    0.3487   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    0.3791    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    1.8166    0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -1.0474   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -0.3142   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530   -1.2154    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -3.0682    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482   -1.5361    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528   -1.6821    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1277   -1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -1.2524   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2515   -1.8724   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2154    4.1120   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695    4.9735    0.7865 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
 16 18  1  0
 18 19  2  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 15 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061305002D          

 19 19  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
    1.1619    3.9097    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
   -0.7912    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    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
   -1.3433    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    3.1251    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
   -0.3297   -0.8227    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
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  5  2  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030102

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9(2)5-7-15(8-6-10(3)4)13(18)11(16)12(17)14(15)19/h5-6,16-17H,7-8H2,1-4H3

> <INCHI_KEY>
KKNXLCGOZLVUHL-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.665253335352816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
3.2258873120000002

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.550137670039021

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.323060571417498

> <JCHEM_PKA_STRONGEST_BASIC>
-4.393482785958573

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
76.82309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030102
     RDKit          3D
Hulupinic acid
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.1208   -1.7626    1.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -1.1464    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -1.8110   -0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0887   -0.0420   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.7781    0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    0.9189   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -0.3851   -0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2688   -1.0200    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -1.3549    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1163   -1.9804    1.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4503   -1.1181   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5374    1.6543   -1.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.2216   -2.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458    3.0660   -1.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    4.1289   -1.8128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5197    3.2164   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432    4.4050    0.2105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1135    1.9179   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.7639    0.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830   -2.3090    2.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -1.0525    2.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -2.5172    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891   -2.7849   -0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845   -1.2414   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5684   -2.0592    0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176    0.3487   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    0.3791    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    1.8166    0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -1.0474   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -0.3142   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530   -1.2154    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -3.0682    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482   -1.5361    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528   -1.6821    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1277   -1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -1.2524   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2515   -1.8724   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2154    4.1120   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695    4.9735    0.7865 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
 16 18  1  0
 18 19  2  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 15 38  1  0
 17 39  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       2.169   7.298   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      -1.477   2.904   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.614   4.689   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.507   4.049   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.645   5.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5    7    9                                                       
CONECT    6    8   10                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9    1    2    5                                                  
CONECT   10    3    4    6                                                  
CONECT   11   12   13   16                                                  
CONECT   12   11   14   17                                                  
CONECT   13   11   15   18                                                  
CONECT   14   12   15   19                                                  
CONECT   15    7    8   13   14                                             
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0030102
HETATM    1  C1  UNL     1      -2.121  -1.763   1.659  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.601  -1.146   0.411  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.698  -1.811  -0.332  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.089  -0.042  -0.052  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.999   0.778   0.520  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.095   0.919  -0.513  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.670  -0.385  -0.911  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.269  -1.020   0.310  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.547  -1.355   0.370  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.116  -1.980   1.586  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.450  -1.118  -0.782  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.537   1.654  -1.662  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.044   1.222  -2.706  1.00  0.00           O  
HETATM   14  C13 UNL     1      -0.446   3.066  -1.313  1.00  0.00           C  
HETATM   15  O2  UNL     1      -1.208   4.129  -1.813  1.00  0.00           O  
HETATM   16  C14 UNL     1       0.520   3.216  -0.400  1.00  0.00           C  
HETATM   17  O3  UNL     1       0.943   4.405   0.211  1.00  0.00           O  
HETATM   18  C15 UNL     1       1.113   1.918  -0.098  1.00  0.00           C  
HETATM   19  O4  UNL     1       2.253   1.764   0.406  1.00  0.00           O  
HETATM   20  H1  UNL     1      -2.983  -2.309   2.151  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.662  -1.053   2.349  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.334  -2.517   1.371  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.289  -2.785  -0.710  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.985  -1.241  -1.246  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.568  -2.059   0.296  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.518   0.349  -1.003  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.577   0.379   1.450  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.411   1.817   0.675  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.161  -1.047  -1.230  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.400  -0.314  -1.718  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.653  -1.215   1.180  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.205  -3.068   1.492  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.148  -1.536   1.708  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.553  -1.682   2.513  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.368  -0.128  -1.233  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.521  -1.252  -0.503  1.00  0.00           H  
HETATM   37  H18 UNL     1       3.252  -1.872  -1.571  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.215   4.112  -1.649  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.370   4.973   0.786  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    4
CONECT    3   23   24   25
CONECT    4    5   26
CONECT    5    6   27   28
CONECT    6    7   12   18
CONECT    7    8   29   30
CONECT    8    9    9   31
CONECT    9   10   11
CONECT   10   32   33   34
CONECT   11   35   36   37
CONECT   12   13   13   14
CONECT   14   15   16   16
CONECT   15   38
CONECT   16   17   18
CONECT   17   39
CONECT   18   19   19
END

HMDB0030102
     RDKit          3D
Hulupinic acid
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.1208   -1.7626    1.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6008   -1.1464    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -1.8110   -0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0887   -0.0420   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.7781    0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    0.9189   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -0.3851   -0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2688   -1.0200    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -1.3549    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1163   -1.9804    1.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4503   -1.1181   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5374    1.6543   -1.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.2216   -2.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458    3.0660   -1.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    4.1289   -1.8128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5197    3.2164   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432    4.4050    0.2105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1135    1.9179   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.7639    0.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830   -2.3090    2.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -1.0525    2.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3343   -2.5172    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891   -2.7849   -0.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845   -1.2414   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5684   -2.0592    0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176    0.3487   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    0.3791    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    1.8166    0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -1.0474   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -0.3142   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530   -1.2154    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050   -3.0682    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482   -1.5361    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528   -1.6821    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -0.1277   -1.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -1.2524   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2515   -1.8724   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2154    4.1120   -1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695    4.9735    0.7865 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
 16 18  1  0
 18 19  2  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 15 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hulupinate	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O)C1=O

InChI Identifier

InChI=1S/C15H20O4/c1-9(2)5-7-15(8-6-10(3)4)13(18)11(16)12(17)14(15)19/h5-6,16-17H,7-8H2,1-4H3

InChI Key

KKNXLCGOZLVUHL-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
Enediol
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: HMDB0030102)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030102)

Source

Endogenous

Endogenous (HMDB: HMDB0030102)

Exogenous

Food

Food (HMDB: HMDB0030102)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0030102)

Role

Biological role

Energy source (HMDB: HMDB0030102)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030102)

Emulsifier (HMDB: HMDB0030102)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	167 - 168 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.6	ALOGPS
logP	3.23	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.82 m³·mol⁻¹	ChemAxon
Polarizability	28.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.057	31661259
DarkChem	[M-H]-	160.861	31661259
DeepCCS	[M+H]+	166.903	30932474
DeepCCS	[M-H]-	164.545	30932474
DeepCCS	[M-2H]-	197.431	30932474
DeepCCS	[M+Na]+	172.996	30932474
AllCCS	[M+H]+	161.4	32859911
AllCCS	[M+H-H2O]+	157.9	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.5	32859911
AllCCS	[M-H]-	165.5	32859911
AllCCS	[M+Na-2H]-	165.9	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hulupinic acid	CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O)C1=O	2827.2	Standard polar	33892256
Hulupinic acid	CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O)C1=O	1842.5	Standard non polar	33892256
Hulupinic acid	CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O)C1=O	1861.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hulupinic acid,1TMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O[Si](C)(C)C)C1=O	2077.2	Semi standard non polar	33892256
Hulupinic acid,2TMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C1=O	2174.4	Semi standard non polar	33892256
Hulupinic acid,1TBDMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O[Si](C)(C)C(C)(C)C)C1=O	2324.8	Semi standard non polar	33892256
Hulupinic acid,2TBDMS,isomer #1	CC(C)=CCC1(CC=C(C)C)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C1=O	2612.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hulupinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aos-9380000000-8eefbb79c7de7289c862	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hulupinic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0006-9014000000-4c45b97bcc9c92996244	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hulupinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hulupinic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 50V, Negative-QTOF	splash10-009i-0900000000-eee7522570c5cd4dd323	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 40V, Negative-QTOF	splash10-0fbl-0900000000-517039b712cdaebafe9c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 40V, Positive-QTOF	splash10-0002-0900000000-6e9146eae6450fa84128	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 30V, Positive-QTOF	splash10-0002-0900000000-c516c0da26f0401f9dcf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 10V, Positive-QTOF	splash10-0a4j-0690000000-14c836e8f713b4437b2f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 20V, Positive-QTOF	splash10-0002-0910000000-6838a81e511b95cfee7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 10V, Negative-QTOF	splash10-03di-0190000000-d49837fa6aff492db30b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 50V, Positive-QTOF	splash10-015d-0900000000-32309a0cb99d5dd8c1c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 20V, Negative-QTOF	splash10-0006-0910000000-1ab698583b5a61998a89	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hulupinic acid 30V, Negative-QTOF	splash10-004l-0900000000-471542cd5704e75cb911	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 10V, Positive-QTOF	splash10-014i-0190000000-cff3a8d39b8e92c1ea2e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 20V, Positive-QTOF	splash10-014j-4790000000-ce7e78655d417a4a1034	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 40V, Positive-QTOF	splash10-00kg-9700000000-fec87bb1d1944db037d9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 10V, Negative-QTOF	splash10-03di-0090000000-8db521826bb33f6e8eef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 20V, Negative-QTOF	splash10-03di-0390000000-b9e3f7a221e5f885434b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 40V, Negative-QTOF	splash10-052b-4930000000-aadf5c3f21f7ff21b38f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 10V, Positive-QTOF	splash10-00kb-0950000000-aa309d1e9289cebab783	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 20V, Positive-QTOF	splash10-02vs-3960000000-d727f59a4d846699b9d8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 40V, Positive-QTOF	splash10-052b-7910000000-ea6d4ce25d3972a72831	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 20V, Negative-QTOF	splash10-03di-0490000000-7a774ebe165f7fb59607	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hulupinic acid 40V, Negative-QTOF	splash10-006t-2910000000-3f7ec77c14aeb9f6278c	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB001900

KNApSAcK ID

C00053327

Chemspider ID

10182038

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12310637

PDB ID

Not Available

ChEBI ID

581942

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Hulupinic acid (HMDB0030102)

MOL for HMDB0030102 (Hulupinic acid)

3D MOL for HMDB0030102 (Hulupinic acid)

3D SDF for HMDB0030102 (Hulupinic acid)

3D-SDF for HMDB0030102 (Hulupinic acid)

PDB for HMDB0030102 (Hulupinic acid)

3D PDB for HMDB0030102 (Hulupinic acid)

SMILES for HMDB0030102 (Hulupinic acid)

INCHI for HMDB0030102 (Hulupinic acid)

Structure for HMDB0030102 (Hulupinic acid)

3D Structure for HMDB0030102 (Hulupinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra