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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:55:47 UTC

Update Date

2022-03-07 02:55:03 UTC

HMDB ID

HMDB0036756

Secondary Accession Numbers

HMDB36756

Metabolite Identification

Common Name

(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid

Description

(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 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. Based on a literature review a significant number of articles have been published on (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid.

Structure

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

  Mrv0541 05061309192D          

 25 28  0  0  0  0            999 V2000
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    3.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3971    3.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5085    2.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  6  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  2  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  2  0  0  0  0
 25 17  1  0  0  0  0
M  END

HMDB0036756
     RDKit          3D
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid
 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.0228    0.3280   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344    0.0981    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.7606    1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    1.8437    1.8799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7588    0.1912    2.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352   -1.3935    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829   -2.1601   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1914   -1.5025   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -0.0221   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    0.6464   -2.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6511    0.5297    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119   -0.0458    1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    0.0550    2.5676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    0.6771    1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0090    0.1668    2.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2495    0.3511    0.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -0.8357    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637   -0.5191   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6234   -0.7455    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7678   -0.4906   -0.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670    0.9530   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076    1.2093   -1.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0825    1.3966   -1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5975    0.2388   -0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296    1.4552    0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596    0.2872   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -0.5350   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0156    1.3171   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7749    0.2335    3.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7819   -1.5553    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274   -1.6959    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056   -2.7506   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7300   -3.0037    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -1.7400   -2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916   -2.0209   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599    1.7235   -2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    0.0910   -3.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221    0.4448   -2.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    1.6292    0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238   -1.1212    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026    0.6239    3.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2416    1.7565    1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7454   -0.7855    2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7495   -1.7662    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911   -0.8608    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322   -1.1448   -1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725   -0.0606    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6123   -1.7986    0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1643   -1.3683   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2757    1.4351   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    0.4138   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    2.1649   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8236    2.3808   -1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    1.3918   -2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -0.6588   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    2.4515    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7551    1.3360    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 11  2  1  0
 24 16  1  0
 24  9  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
M  END

  Mrv0541 05061309192D          

 25 28  0  0  0  0            999 V2000
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0046    3.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3971    3.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5085    2.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18  6  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  2  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 10  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  2  0  0  0  0
 25 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036756

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCCC(C)(C1C(O)C(O)C13CC(CO)C(C1)CCC23)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-18-6-3-7-19(2,17(24)25)15(18)14(22)16(23)20-8-11(4-5-13(18)20)12(9-20)10-21/h11-16,21-23H,3-10H2,1-2H3,(H,24,25)

> <INCHI_KEY>
FQXFNQBHZJYODR-UHFFFAOYSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.78467150187949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
1.568990744666666

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.522657935567175

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.456753812358466

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5278841983177789

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
92.23779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036756
     RDKit          3D
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid
 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.0228    0.3280   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344    0.0981    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.7606    1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    1.8437    1.8799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7588    0.1912    2.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352   -1.3935    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829   -2.1601   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1914   -1.5025   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -0.0221   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    0.6464   -2.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6511    0.5297    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119   -0.0458    1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    0.0550    2.5676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    0.6771    1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0090    0.1668    2.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2495    0.3511    0.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -0.8357    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637   -0.5191   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6234   -0.7455    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7678   -0.4906   -0.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670    0.9530   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076    1.2093   -1.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0825    1.3966   -1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5975    0.2388   -0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296    1.4552    0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596    0.2872   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -0.5350   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0156    1.3171   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7749    0.2335    3.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7819   -1.5553    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274   -1.6959    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056   -2.7506   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7300   -3.0037    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -1.7400   -2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916   -2.0209   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599    1.7235   -2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    0.0910   -3.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221    0.4448   -2.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    1.6292    0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238   -1.1212    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026    0.6239    3.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2416    1.7565    1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7454   -0.7855    2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7495   -1.7662    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911   -0.8608    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322   -1.1448   -1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725   -0.0606    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6123   -1.7986    0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1643   -1.3683   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2757    1.4351   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    0.4138   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    2.1649   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8236    2.3808   -1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    1.3918   -2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -0.6588   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    2.4515    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7551    1.3360    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 11  2  1  0
 24 16  1  0
 24  9  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  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       5.108   0.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.061   5.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.129   1.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.722   0.398   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.618   1.124   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.628   2.877   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.265   2.796   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.263   2.606   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.099   4.917   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.934   4.833   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.616   4.038   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.933   3.166   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.194   1.568   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.609   6.370   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.608   5.829   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.905   6.373   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.282   4.089   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    6    7                                                       
CONECT    4    5   11                                                       
CONECT    5    4   13                                                       
CONECT    6    3   18                                                       
CONECT    7    3   19                                                       
CONECT    8   11   20                                                       
CONECT    9   12   20                                                       
CONECT   10   12   21                                                       
CONECT   11    4    8   12                                                  
CONECT   12    9   10   11                                                  
CONECT   13    5   18   20                                                  
CONECT   14   15   16   22                                                  
CONECT   15   14   18   19                                                  
CONECT   16   14   20   23                                                  
CONECT   17   19   24   25                                                  
CONECT   18    1    6   13   15                                             
CONECT   19    2    7   15   17                                             
CONECT   20    8    9   13   16                                             
CONECT   21   10                                                            
CONECT   22   14                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   17                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0036756
HETATM    1  C1  UNL     1      -4.023   0.328  -0.818  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.034   0.098   0.287  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.650   0.761   1.471  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.161   1.844   1.880  1.00  0.00           O  
HETATM    5  O2  UNL     1      -4.759   0.191   2.119  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.035  -1.393   0.534  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.183  -2.160  -0.410  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.191  -1.503  -1.235  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.891  -0.022  -1.029  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.313   0.646  -2.325  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.651   0.530   0.160  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.912  -0.046   1.357  1.00  0.00           C  
HETATM   13  O3  UNL     1      -1.517   0.055   2.568  1.00  0.00           O  
HETATM   14  C11 UNL     1       0.397   0.677   1.516  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.009   0.167   2.664  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.249   0.351   0.346  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.188  -0.836   0.627  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.364  -0.519  -0.302  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.623  -0.746   0.507  1.00  0.00           C  
HETATM   20  O5  UNL     1       5.768  -0.491  -0.227  1.00  0.00           O  
HETATM   21  C16 UNL     1       3.267   0.953  -0.633  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.608   1.209  -1.954  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.083   1.397  -1.809  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.597   0.239  -0.963  1.00  0.00           C  
HETATM   25  C20 UNL     1       2.330   1.455   0.415  1.00  0.00           C  
HETATM   26  H1  UNL     1      -5.060   0.287  -0.341  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.114  -0.535  -1.520  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.016   1.317  -1.269  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.775   0.234   3.113  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.782  -1.555   1.593  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.127  -1.696   0.487  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.906  -2.751  -1.062  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.730  -3.004   0.203  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.375  -1.740  -2.330  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.192  -2.021  -1.088  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.160   1.724  -2.323  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.713   0.091  -3.117  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.322   0.445  -2.659  1.00  0.00           H  
HETATM   39  H14 UNL     1      -1.496   1.629   0.150  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.624  -1.121   1.180  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.103   0.624   3.235  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.242   1.756   1.690  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.745  -0.785   2.759  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.749  -1.766   0.280  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.491  -0.861   1.680  1.00  0.00           H  
HETATM   46  H21 UNL     1       3.332  -1.145  -1.206  1.00  0.00           H  
HETATM   47  H22 UNL     1       4.573  -0.061   1.388  1.00  0.00           H  
HETATM   48  H23 UNL     1       4.612  -1.799   0.888  1.00  0.00           H  
HETATM   49  H24 UNL     1       6.164  -1.368  -0.473  1.00  0.00           H  
HETATM   50  H25 UNL     1       4.276   1.435  -0.596  1.00  0.00           H  
HETATM   51  H26 UNL     1       2.816   0.414  -2.672  1.00  0.00           H  
HETATM   52  H27 UNL     1       3.000   2.165  -2.366  1.00  0.00           H  
HETATM   53  H28 UNL     1       0.824   2.381  -1.404  1.00  0.00           H  
HETATM   54  H29 UNL     1       0.764   1.392  -2.855  1.00  0.00           H  
HETATM   55  H30 UNL     1       1.053  -0.659  -1.493  1.00  0.00           H  
HETATM   56  H31 UNL     1       1.934   2.452   0.290  1.00  0.00           H  
HETATM   57  H32 UNL     1       2.755   1.336   1.455  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    6   11
CONECT    3    4    4    5
CONECT    5   29
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   11   24
CONECT   10   36   37   38
CONECT   11   12   39
CONECT   12   13   14   40
CONECT   13   41
CONECT   14   15   16   42
CONECT   15   43
CONECT   16   17   24   25
CONECT   17   18   44   45
CONECT   18   19   21   46
CONECT   19   20   47   48
CONECT   20   49
CONECT   21   22   25   50
CONECT   22   23   51   52
CONECT   23   24   53   54
CONECT   24   55
CONECT   25   56   57
END

HMDB0036756
     RDKit          3D
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid
 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.0228    0.3280   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344    0.0981    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.7606    1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    1.8437    1.8799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7588    0.1912    2.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352   -1.3935    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829   -2.1601   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1914   -1.5025   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -0.0221   -1.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    0.6464   -2.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6511    0.5297    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119   -0.0458    1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    0.0550    2.5676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    0.6771    1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0090    0.1668    2.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2495    0.3511    0.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -0.8357    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3637   -0.5191   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6234   -0.7455    0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7678   -0.4906   -0.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670    0.9530   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076    1.2093   -1.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0825    1.3966   -1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5975    0.2388   -0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296    1.4552    0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596    0.2872   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -0.5350   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0156    1.3171   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7749    0.2335    3.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7819   -1.5553    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274   -1.6959    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056   -2.7506   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7300   -3.0037    0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3752   -1.7400   -2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916   -2.0209   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599    1.7235   -2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    0.0910   -3.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221    0.4448   -2.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    1.6292    0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238   -1.1212    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026    0.6239    3.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2416    1.7565    1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7454   -0.7855    2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7495   -1.7662    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911   -0.8608    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3322   -1.1448   -1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725   -0.0606    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6123   -1.7986    0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1643   -1.3683   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2757    1.4351   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163    0.4138   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    2.1649   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8236    2.3808   -1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    1.3918   -2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -0.6588   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    2.4515    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7551    1.3360    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 11  2  1  0
 24 16  1  0
 24  9  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(ent-6a,7a,16AlphaH)-6,7,17-trihydroxy-19-kauranoate	Generator
(ent-6a,7a,16AlphaH)-6,7,17-trihydroxy-19-kauranoic acid	Generator
(ent-6alpha,7alpha,16AlphaH)-6,7,17-trihydroxy-19-kauranoate	Generator
(ent-6Α,7α,16alphah)-6,7,17-trihydroxy-19-kauranoate	Generator
(ent-6Α,7α,16alphah)-6,7,17-trihydroxy-19-kauranoic acid	Generator
2,3-Dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

56064-72-3

SMILES

CC12CCCC(C)(C1C(O)C(O)C13CC(CO)C(C1)CCC23)C(O)=O

InChI Identifier

InChI=1S/C20H32O5/c1-18-6-3-7-19(2,17(24)25)15(18)14(22)16(23)20-8-11(4-5-13(18)20)12(9-20)10-21/h11-16,21-23H,3-10H2,1-2H3,(H,24,25)

InChI Key

FQXFNQBHZJYODR-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
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036756)

Source

Endogenous

Endogenous (HMDB: HMDB0036756)

Plant

Fabaceae (HMDB: HMDB0036756)

Animal

Animal (HMDB: HMDB0036756)

Exogenous

Food

Food (HMDB: HMDB0036756)

Pulse

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0036756)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036756)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036756)

Lipid metabolism pathway (HMDB: HMDB0036756)

Cellular process

Cell signaling (HMDB: HMDB0036756)

Biochemical process

Lipid transport (HMDB: HMDB0036756)

Role

Biological role

Energy source (HMDB: HMDB0036756)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036756)

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
Water Solubility	1.37 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.57	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.24 m³·mol⁻¹	ChemAxon
Polarizability	38.78 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
DarkChem	[M+H]+	182.188	31661259
DarkChem	[M-H]-	177.788	31661259
DeepCCS	[M-2H]-	223.062	30932474
DeepCCS	[M+Na]+	198.703	30932474
AllCCS	[M+H]+	186.1	32859911
AllCCS	[M+H-H2O]+	183.5	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.1	32859911
AllCCS	[M-H]-	188.3	32859911
AllCCS	[M+Na-2H]-	188.7	32859911
AllCCS	[M+HCOO]-	189.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid	CC12CCCC(C)(C1C(O)C(O)C13CC(CO)C(C1)CCC23)C(O)=O	2772.5	Standard polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid	CC12CCCC(C)(C1C(O)C(O)C13CC(CO)C(C1)CCC23)C(O)=O	2831.6	Standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid	CC12CCCC(C)(C1C(O)C(O)C13CC(CO)C(C1)CCC23)C(O)=O	3107.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TMS,isomer #1	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C)C(O)C13CC(CO)C(CCC21)C3	3109.5	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TMS,isomer #2	CC1(C(=O)O)CCCC2(C)C1C(O)C(O[Si](C)(C)C)C13CC(CO)C(CCC21)C3	3103.2	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TMS,isomer #3	CC1(C(=O)O)CCCC2(C)C1C(O)C(O)C13CC(CCC21)C(CO[Si](C)(C)C)C3	3127.0	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TMS,isomer #4	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O)C(O)C13CC(CO)C(CCC21)C3	3048.7	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TMS,isomer #1	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C)C(O)C13CC(CO)C(CCC21)C3	2972.0	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TMS,isomer #2	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C)C(O[Si](C)(C)C)C13CC(CO)C(CCC21)C3	3041.4	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TMS,isomer #3	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C)C(O)C13CC(CCC21)C(CO[Si](C)(C)C)C3	3058.0	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TMS,isomer #4	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O)C(O[Si](C)(C)C)C13CC(CO)C(CCC21)C3	2955.5	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TMS,isomer #5	CC1(C(=O)O)CCCC2(C)C1C(O)C(O[Si](C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C)C3	3056.1	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TMS,isomer #6	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O)C(O)C13CC(CCC21)C(CO[Si](C)(C)C)C3	3033.9	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TMS,isomer #1	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C)C(O[Si](C)(C)C)C13CC(CO)C(CCC21)C3	2943.9	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TMS,isomer #2	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C)C(O)C13CC(CCC21)C(CO[Si](C)(C)C)C3	2936.4	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TMS,isomer #3	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C)C(O[Si](C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C)C3	2970.3	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TMS,isomer #4	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O)C(O[Si](C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C)C3	2920.9	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,4TMS,isomer #1	CC1(C(=O)O[Si](C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C)C(O[Si](C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C)C3	2920.7	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TBDMS,isomer #1	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O)C13CC(CO)C(CCC21)C3	3344.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TBDMS,isomer #2	CC1(C(=O)O)CCCC2(C)C1C(O)C(O[Si](C)(C)C(C)(C)C)C13CC(CO)C(CCC21)C3	3341.3	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TBDMS,isomer #3	CC1(C(=O)O)CCCC2(C)C1C(O)C(O)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3392.9	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,1TBDMS,isomer #4	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O)C(O)C13CC(CO)C(CCC21)C3	3320.9	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TBDMS,isomer #1	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O)C13CC(CO)C(CCC21)C3	3463.5	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TBDMS,isomer #2	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C13CC(CO)C(CCC21)C3	3514.0	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TBDMS,isomer #3	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3541.5	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TBDMS,isomer #4	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O)C(O[Si](C)(C)C(C)(C)C)C13CC(CO)C(CCC21)C3	3439.5	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TBDMS,isomer #5	CC1(C(=O)O)CCCC2(C)C1C(O)C(O[Si](C)(C)C(C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3537.8	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,2TBDMS,isomer #6	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O)C(O)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3548.7	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TBDMS,isomer #1	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C13CC(CO)C(CCC21)C3	3631.6	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TBDMS,isomer #2	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3633.9	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TBDMS,isomer #3	CC1(C(=O)O)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3668.1	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,3TBDMS,isomer #4	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O)C(O[Si](C)(C)C(C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3634.4	Semi standard non polar	33892256
(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid,4TBDMS,isomer #1	CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC2(C)C1C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C13CC(CCC21)C(CO[Si](C)(C)C(C)(C)C)C3	3818.6	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 - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-008i-2948000000-cfa61bd9c75f632da1c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid GC-MS (4 TMS) - 70eV, Positive	splash10-004i-1011249000-dce997746b7dc7b06d5c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 10V, Positive-QTOF	splash10-0f79-0019000000-228ac8907bad784f002c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 20V, Positive-QTOF	splash10-00kr-0149000000-d812897831c56df9e301	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 40V, Positive-QTOF	splash10-000i-3294000000-3b26920672c3e20dcb1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 10V, Negative-QTOF	splash10-0udi-0019000000-3700a0981b32106493cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 20V, Negative-QTOF	splash10-0zpr-0049000000-f14f451861e48bb96f0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 40V, Negative-QTOF	splash10-004i-2094000000-a9d9a89a82b5513f1fe1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 10V, Negative-QTOF	splash10-0udi-0009000000-380bcdac41775c30cac2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 20V, Negative-QTOF	splash10-0udi-0029000000-bd410a1d72124635fcd9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 40V, Negative-QTOF	splash10-0uk9-0049000000-faa268b52710d38766b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 10V, Positive-QTOF	splash10-0udi-0009000000-04fec15919a137f4a57e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 20V, Positive-QTOF	splash10-1009-1079000000-647b0af7d7410a8a5f16	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid 40V, Positive-QTOF	splash10-0pvr-8579000000-d98eb42e551b9f4c41e0	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

FDB015695

KNApSAcK ID

Not Available

Chemspider ID

35014236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752049

PDB ID

Not Available

ChEBI ID

175527

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid (HMDB0036756)

MOL for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D MOL for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D SDF for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D-SDF for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

PDB for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D PDB for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

SMILES for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

INCHI for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

Structure for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D Structure for HMDB0036756 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra