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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 09:04:45 UTC

Update Date

2021-09-24 09:04:45 UTC

HMDB ID

HMDB0304345

Secondary Accession Numbers

None

Metabolite Identification

Common Name

ent-7alpha-hydroxykaur-16-en-19-oate

Description

Ent-7alpha-hydroxykaur-16-en-19-oate is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ent-7alpha-hydroxykaur-16-en-19-oate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ent-7alpha-hydroxykaur-16-en-19-oate can be found in a number of food items such as greenthread tea, cardamom, agave, and hickory nut, which makes ent-7alpha-hydroxykaur-16-en-19-oate a potential biomarker for the consumption of these food products.

Structure

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

HMDB0304345
     RDKit          3D
ent-7alpha-hydroxykaur-16-en-19-oate
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.3173    1.2784    1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.9815    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140    0.9152    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    0.9915   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852    1.4957   -0.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884    0.6286   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.8302   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -1.3122   -0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965   -0.2850   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -0.7893   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9120   -1.4520   -1.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -1.8957    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -2.4826    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757   -1.6128   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -0.1751    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9450    0.6117   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    0.0721    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311   -0.8829    2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8779    1.3333    2.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623    0.3161   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662    1.4719    0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    2.0749   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393    2.6151   -1.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3480    1.2783    1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
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 19 48  1  0
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 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
M  END

  Mrv1533004171506552D          

 23 26  0  0  0  0            999 V2000
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1637   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9836   -1.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
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  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304345

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCCC(C)(C1CC(O)C13CC(CCC21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-12-10-20-11-13(12)5-6-14(20)18(2)7-4-8-19(3,17(22)23)15(18)9-16(20)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)

> <INCHI_KEY>
KMLXVEXJZSTMBV-UHFFFAOYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.29285507336874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
3.5770196973333337

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.703987792818853

> <JCHEM_PKA_STRONGEST_BASIC>
-0.34940698104018775

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
88.87909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304345
     RDKit          3D
ent-7alpha-hydroxykaur-16-en-19-oate
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.3173    1.2784    1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.9815    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140    0.9152    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    0.9915   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852    1.4957   -0.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884    0.6286   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.8302   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3727    2.1008   -2.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
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 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.408   1.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.778  -3.515   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.984  -0.707   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.230  -3.248   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.166  -4.471   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.703  -3.447   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   21                                             
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17   20                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   12                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12                                                       
CONECT   21    6   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0304345
HETATM    1  C1  UNL     1       4.317   1.278   1.919  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.388   0.982   1.034  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.914   0.915   1.196  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.309   0.992  -0.168  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.485   1.496  -0.990  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.588   0.629  -0.390  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.344  -0.830  -0.564  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.962  -1.312  -0.444  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.896  -0.285  -0.774  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.481  -0.789  -0.593  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.912  -1.452  -1.920  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.616  -1.896   0.429  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.001  -2.483   0.456  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.076  -1.613  -0.066  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.792  -0.175   0.167  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.945   0.612  -0.477  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.903   0.072   1.620  1.00  0.00           C  
HETATM   18  O1  UNL     1      -3.031  -0.883   2.462  1.00  0.00           O  
HETATM   19  O2  UNL     1      -2.878   1.333   2.185  1.00  0.00           O  
HETATM   20  C18 UNL     1      -1.462   0.316  -0.353  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.966   1.472   0.443  1.00  0.00           C  
HETATM   22  C20 UNL     1       0.264   2.075  -0.208  1.00  0.00           C  
HETATM   23  O3  UNL     1       0.039   2.615  -1.441  1.00  0.00           O  
HETATM   24  H1  UNL     1       5.348   1.278   1.625  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.099   1.528   2.946  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.571   1.793   1.820  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.717   0.010   1.759  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.379   1.296  -2.057  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.723   2.545  -0.738  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.579   0.924  -0.732  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.973  -1.363   0.212  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.797  -1.134  -1.535  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.745  -1.662   0.599  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.777  -2.198  -1.086  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.021  -0.140  -1.897  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.685  -0.895  -2.437  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.036  -1.470  -2.639  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.198  -2.492  -1.813  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.083  -2.727   0.165  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.368  -1.594   1.445  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.998  -3.444  -0.153  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.216  -2.838   1.489  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.374  -1.885  -1.098  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.998  -1.855   0.556  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.665   0.929  -1.506  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.143   1.544   0.094  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.885   0.023  -0.453  1.00  0.00           H  
HETATM   48  H25 UNL     1      -2.534   1.539   3.104  1.00  0.00           H  
HETATM   49  H26 UNL     1      -1.707   0.739  -1.378  1.00  0.00           H  
HETATM   50  H27 UNL     1      -1.726   2.259   0.438  1.00  0.00           H  
HETATM   51  H28 UNL     1      -0.707   1.236   1.490  1.00  0.00           H  
HETATM   52  H29 UNL     1       0.610   2.886   0.465  1.00  0.00           H  
HETATM   53  H30 UNL     1       0.373   2.101  -2.203  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3    6
CONECT    3    4   26   27
CONECT    4    5    9   22
CONECT    5    6   28   29
CONECT    6    7   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   35
CONECT   10   11   12   20
CONECT   11   36   37   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   17   20
CONECT   16   45   46   47
CONECT   17   18   18   19
CONECT   19   48
CONECT   20   21   49
CONECT   21   22   50   51
CONECT   22   23   52
CONECT   23   53
END

HMDB0304345
     RDKit          3D
ent-7alpha-hydroxykaur-16-en-19-oate
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.3173    1.2784    1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.9815    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9140    0.9152    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    0.9915   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852    1.4957   -0.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884    0.6286   -0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.8302   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -1.3122   -0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965   -0.2850   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -0.7893   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9120   -1.4520   -1.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -1.8957    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -2.4826    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757   -1.6128   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -0.1751    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9450    0.6117   -0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9028    0.0721    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0311   -0.8829    2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8779    1.3333    2.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623    0.3161   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662    1.4719    0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    2.0749   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393    2.6151   -1.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3480    1.2783    1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0989    1.5276    2.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713    1.7933    1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7171    0.0097    1.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3794    1.2962   -2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    2.5450   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5795    0.9240   -0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -1.3629    0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7970   -1.1343   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445   -1.6625    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7769   -2.1982   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207   -0.1400   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854   -0.8951   -2.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -1.4700   -2.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -2.4923   -1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -2.7270    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3679   -1.5943    1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -3.4438   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159   -2.8382    1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3740   -1.8849   -1.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981   -1.8549    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6652    0.9292   -1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434    1.5436    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8854    0.0232   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339    1.5389    3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7072    0.7394   -1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7255    2.2591    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068    1.2359    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105    2.8861    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3727    2.1008   -2.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  6  2  1  0
 20 10  1  0
  9  4  1  0
 22  4  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
ent-7a-Hydroxykaur-16-en-19-Oate	Generator
ent-7a-Hydroxykaur-16-en-19-Oic acid	Generator
ent-7alpha-Hydroxykaur-16-en-19-Oic acid	Generator
ent-7Α-hydroxykaur-16-en-19-Oate	Generator
ent-7Α-hydroxykaur-16-en-19-Oic acid	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.457

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C1CC(O)C13CC(CCC21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-12-10-20-11-13(12)5-6-14(20)18(2)7-4-8-19(3,17(22)23)15(18)9-16(20)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)

InChI Key

KMLXVEXJZSTMBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Not Available

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Gibberellin A12 Biosynthesis (PathBank: SMP0012068)

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.94	ALOGPS
logP	3.58	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.88 m³·mol⁻¹	ChemAxon
Polarizability	36.29 Å³	ChemAxon
Number of Rings	4	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
AllCCS	[M+H]+	180.11	32859911
AllCCS	[M+H-H2O]+	177.236	32859911
AllCCS	[M+Na]+	183.529	32859911
AllCCS	[M+NH4]+	182.767	32859911
AllCCS	[M-H]-	183.809	32859911
AllCCS	[M+Na-2H]-	183.996	32859911
AllCCS	[M+HCOO]-	184.339	32859911
DeepCCS	[M-2H]-	212.696	30932474
DeepCCS	[M+Na]+	188.261	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 10V, Positive-QTOF	splash10-0uxr-0049000000-398a7bb43ad218bc6267	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 20V, Positive-QTOF	splash10-0zmi-0295000000-138f465835e3f0c23bf7	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 40V, Positive-QTOF	splash10-014i-4891000000-2e0ebeb9b87a4c5f58be	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 10V, Negative-QTOF	splash10-014i-0069000000-489d02266ce8a1960780	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 20V, Negative-QTOF	splash10-0601-0093000000-79f715fdec769df35e45	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 40V, Negative-QTOF	splash10-0pi0-1091000000-bb3dc53f447ac65af09d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 10V, Positive-QTOF	splash10-01b9-0098000000-210144b2576f009ea64d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 20V, Positive-QTOF	splash10-0100-0292000000-82048a84fa7b268332b3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 40V, Positive-QTOF	splash10-0ab9-2940000000-dc27ad62fa88dffc8708	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 10V, Negative-QTOF	splash10-014i-0009000000-062ad2a35e11d303cf23	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 20V, Negative-QTOF	splash10-014i-0019000000-b12eb29b9d3669f54e5e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-7alpha-hydroxykaur-16-en-19-oate 40V, Negative-QTOF	splash10-014i-2029000000-0d372a4aab6a82512436	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB030845

KNApSAcK ID

Not Available

Chemspider ID

24808059

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14487041

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for ent-7alpha-hydroxykaur-16-en-19-oate (HMDB0304345)

MOL for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D MOL for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D SDF for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D-SDF for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

PDB for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D PDB for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

SMILES for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

INCHI for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

Structure for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D Structure for HMDB0304345 (ent-7alpha-hydroxykaur-16-en-19-oate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra