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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:07:06 UTC

Update Date

2022-03-07 02:55:07 UTC

HMDB ID

HMDB0036930

Secondary Accession Numbers

HMDB36930

Metabolite Identification

Common Name

Grandiflorolic acid

Description

Grandiflorolic acid, also known as grandiflorolate, 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 Grandiflorolic acid.

Structure

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

HMDB0036930
     RDKit          3D
Grandiflorolic acid
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.1573    0.9155    1.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096    0.4028    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -0.9615    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439   -1.8764    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -1.4024    1.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475   -0.9948   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961   -0.8816   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768   -1.8024   -1.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6012   -1.5444    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0586   -1.3579    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    0.0534    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163    1.0187    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    1.9810   -0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717    1.8753    1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066    3.1385    1.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5888    1.3111    2.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    0.4424   -0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    1.4733   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9623    0.8353   -1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610    0.0773   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.6271   -1.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0999    1.0208    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2717    1.5111    1.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    0.3182    2.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    1.9176    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -1.4010    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -1.9077    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213   -2.8955    0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.3163    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.6747    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899   -1.9440   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210   -1.3476   -2.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3881   -2.7966   -1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205   -1.9192   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -1.2537    1.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -2.6571    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7097   -2.1052    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555   -1.5433   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.2394    0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5100    0.1131    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6710    1.3152   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312    2.6646   -1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    2.4610   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9292    1.6955    2.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9140    0.3174   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6589    2.1440   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    2.1739   -0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    1.6898   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8176    0.2604   -2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -1.5449   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996    0.0691   -1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711    1.9155   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411    2.4039    1.5938 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  2  1  0
 21  3  1  0
 20  6  1  0
 17  7  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
M  END


  Mrv0541 05061309252D          

 23 26  0  0  0  0            999 V2000
   -0.6778    1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7608    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
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    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
    1.9121    2.4782    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
    0.1409    1.3963    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
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    2.0342    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    2.1629    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
    0.5612    2.8399    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
    5.5084    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 12  1  2  0  0  0  0
 13  5  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 15  6  1  0  0  0  0
 16 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19  9  1  0  0  0  0
 19 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 10  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  2  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036930

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O

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

> <INCHI_KEY>
GVGJRXSJJHLPGZ-UHFFFAOYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.24451233428009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.7329271573333345

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.711390057630677

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7040066239125204

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7380396898317859

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
88.72509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036930
     RDKit          3D
Grandiflorolic acid
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.1573    0.9155    1.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096    0.4028    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -0.9615    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439   -1.8764    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -1.4024    1.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475   -0.9948   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961   -0.8816   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768   -1.8024   -1.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6012   -1.5444    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0586   -1.3579    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    0.0534    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163    1.0187    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    1.9810   -0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717    1.8753    1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066    3.1385    1.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5888    1.3111    2.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    0.4424   -0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    1.4733   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9623    0.8353   -1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610    0.0773   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.6271   -1.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0999    1.0208    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2717    1.5111    1.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    0.3182    2.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    1.9176    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -1.4010    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -1.9077    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213   -2.8955    0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.3163    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.6747    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899   -1.9440   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210   -1.3476   -2.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3881   -2.7966   -1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205   -1.9192   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -1.2537    1.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -2.6571    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7097   -2.1052    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555   -1.5433   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.2394    0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5100    0.1131    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6710    1.3152   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312    2.6646   -1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    2.4610   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9292    1.6955    2.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9140    0.3174   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6589    2.1440   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    2.1739   -0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    1.6898   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8176    0.2604   -2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -1.5449   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996    0.0691   -1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711    1.9155   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411    2.4039    1.5938 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  2  1  0
 21  3  1  0
 20  6  1  0
 17  7  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  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      -1.265   2.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.108   0.826   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.061   5.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.129   1.420   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.722   0.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.099   4.917   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.618   1.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.628   2.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.053   2.140   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       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.378   3.797   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   4.037   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       1.047   5.301   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.904   6.373   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.282   4.089   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    8    9                                                       
CONECT    5    6   13                                                       
CONECT    6    5   15                                                       
CONECT    7   10   14                                                       
CONECT    8    4   18                                                       
CONECT    9    4   19                                                       
CONECT   10    7   20                                                       
CONECT   11   13   20                                                       
CONECT   12    1   13   16                                                  
CONECT   13    5   11   12                                                  
CONECT   14    7   18   19                                                  
CONECT   15    6   18   20                                                  
CONECT   16   12   20   21                                                  
CONECT   17   19   22   23                                                  
CONECT   18    2    8   14   15                                             
CONECT   19    3    9   14   17                                             
CONECT   20   10   11   15   16                                             
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0036930
HETATM    1  C1  UNL     1       4.157   0.916   1.835  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.310   0.403   0.977  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.362  -0.961   0.396  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.444  -1.876   1.130  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.998  -1.402   1.192  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.647  -0.995  -0.224  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.796  -0.882  -0.543  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.077  -1.802  -1.772  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.601  -1.544   0.555  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.059  -1.358   0.179  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.432   0.053   0.489  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.416   1.019   0.006  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.215   1.981  -0.935  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.972   1.875   1.110  1.00  0.00           C  
HETATM   15  O1  UNL     1      -1.907   3.138   1.054  1.00  0.00           O  
HETATM   16  O2  UNL     1      -1.589   1.311   2.310  1.00  0.00           O  
HETATM   17  C15 UNL     1      -1.349   0.442  -0.877  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.308   1.473  -1.264  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.962   0.835  -1.780  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.561   0.077  -0.645  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.884  -0.627  -1.029  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.100   1.021   0.366  1.00  0.00           C  
HETATM   23  O3  UNL     1       1.272   1.511   1.315  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.990   0.318   2.178  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.067   1.918   2.224  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.356  -1.401   0.389  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.795  -1.908   2.183  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.521  -2.896   0.725  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.394  -2.316   1.417  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.791  -0.675   1.959  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.990  -1.944  -0.770  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.821  -1.348  -2.435  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.388  -2.797  -1.481  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.120  -1.919  -2.352  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.346  -1.254   1.566  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.377  -2.657   0.463  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.710  -2.105   0.674  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.155  -1.543  -0.910  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.464   0.239   0.092  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.510   0.113   1.612  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.671   1.315  -1.696  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.531   2.665  -1.438  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.027   2.461  -0.368  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.929   1.696   2.955  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.914   0.317  -1.870  1.00  0.00           H  
HETATM   46  H23 UNL     1      -0.659   2.144  -2.106  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.044   2.174  -0.465  1.00  0.00           H  
HETATM   48  H25 UNL     1       1.655   1.690  -2.009  1.00  0.00           H  
HETATM   49  H26 UNL     1       0.818   0.260  -2.703  1.00  0.00           H  
HETATM   50  H27 UNL     1       2.701  -1.545  -1.587  1.00  0.00           H  
HETATM   51  H28 UNL     1       3.600   0.069  -1.459  1.00  0.00           H  
HETATM   52  H29 UNL     1       2.471   1.915  -0.226  1.00  0.00           H  
HETATM   53  H30 UNL     1       1.541   2.404   1.594  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   22
CONECT    3    4   21   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   20   31
CONECT    7    8    9   17
CONECT    8   32   33   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   14   17
CONECT   13   41   42   43
CONECT   14   15   15   16
CONECT   16   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   22
CONECT   21   50   51
CONECT   22   23   52
CONECT   23   53
END

HMDB0036930
     RDKit          3D
Grandiflorolic acid
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.1573    0.9155    1.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096    0.4028    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -0.9615    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439   -1.8764    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -1.4024    1.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475   -0.9948   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961   -0.8816   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768   -1.8024   -1.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6012   -1.5444    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0586   -1.3579    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    0.0534    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163    1.0187    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152    1.9810   -0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717    1.8753    1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066    3.1385    1.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5888    1.3111    2.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    0.4424   -0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    1.4733   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9623    0.8353   -1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610    0.0773   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.6271   -1.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0999    1.0208    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2717    1.5111    1.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    0.3182    2.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    1.9176    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -1.4010    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -1.9077    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213   -2.8955    0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -2.3163    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.6747    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899   -1.9440   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210   -1.3476   -2.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3881   -2.7966   -1.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205   -1.9192   -2.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -1.2537    1.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -2.6571    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7097   -2.1052    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555   -1.5433   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.2394    0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5100    0.1131    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6710    1.3152   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312    2.6646   -1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0269    2.4610   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9292    1.6955    2.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9140    0.3174   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6589    2.1440   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    2.1739   -0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    1.6898   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8176    0.2604   -2.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006   -1.5449   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996    0.0691   -1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711    1.9155   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411    2.4039    1.5938 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  2  1  0
 21  3  1  0
 20  6  1  0
 17  7  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 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
Grandiflorolate	Generator
Gradifloric acid	HMDB
Grandifloric acid	HMDB
15-Hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

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

Traditional Name

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

CAS Registry Number

22338-69-8

SMILES

CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O

InChI Identifier

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

InChI Key

GVGJRXSJJHLPGZ-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

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036930)

Source

Endogenous

Endogenous (HMDB: HMDB0036930)

Plant

Plant (HMDB: HMDB0036930)

Animal

Animal (HMDB: HMDB0036930)

Exogenous

Food

Food (HMDB: HMDB0036930)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0036930)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036930)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036930)

Lipid metabolism pathway (HMDB: HMDB0036930)

Cellular process

Cell signaling (HMDB: HMDB0036930)

Biochemical process

Lipid transport (HMDB: HMDB0036930)

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036930)

Agriculture

Pesticide (HMDB: HMDB0036930)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	216 - 218 °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	0.022 g/L	ALOGPS
logP	3.29	ALOGPS
logP	3.73	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-0.74	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	88.73 m³·mol⁻¹	ChemAxon
Polarizability	36.24 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]+	176.293	31661259
DarkChem	[M-H]-	171.452	31661259
DeepCCS	[M-2H]-	212.686	30932474
DeepCCS	[M+Na]+	188.251	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.5	32859911
AllCCS	[M-H]-	183.6	32859911
AllCCS	[M+Na-2H]-	183.8	32859911
AllCCS	[M+HCOO]-	184.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.78 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4886 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2409.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	336.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	506.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	561.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	739.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1239.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1469.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	443.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	306.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	387.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	32.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Grandiflorolic acid	CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O	3270.5	Standard polar	33892256
Grandiflorolic acid	CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O	2471.8	Standard non polar	33892256
Grandiflorolic acid	CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O	2641.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Grandiflorolic acid,1TMS,isomer #1	C=C1C2CCC3C4(C)CCCC(C)(C(=O)O)C4CCC3(C2)C1O[Si](C)(C)C	2663.6	Semi standard non polar	33892256
Grandiflorolic acid,1TMS,isomer #2	C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C)C4CCC3(C2)C1O	2569.7	Semi standard non polar	33892256
Grandiflorolic acid,2TMS,isomer #1	C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C)C4CCC3(C2)C1O[Si](C)(C)C	2538.0	Semi standard non polar	33892256
Grandiflorolic acid,1TBDMS,isomer #1	C=C1C2CCC3C4(C)CCCC(C)(C(=O)O)C4CCC3(C2)C1O[Si](C)(C)C(C)(C)C	2897.5	Semi standard non polar	33892256
Grandiflorolic acid,1TBDMS,isomer #2	C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C4CCC3(C2)C1O	2839.1	Semi standard non polar	33892256
Grandiflorolic acid,2TBDMS,isomer #1	C=C1C2CCC3C4(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C4CCC3(C2)C1O[Si](C)(C)C(C)(C)C	3033.0	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 - Grandiflorolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0293000000-6d81233578562a5d26aa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grandiflorolic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0092-7057900000-207d915177a4f066ae38	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Grandiflorolic 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 - Grandiflorolic acid 10V, Positive-QTOF	splash10-0uxr-0049000000-4b652304c7d71bce7fda	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Positive-QTOF	splash10-0zfr-0295000000-15eccd134beb9a35a29c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Positive-QTOF	splash10-0pvi-6891000000-4421f81b0af8e634e443	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 10V, Negative-QTOF	splash10-014i-0069000000-718245f7e353ddb6470b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Negative-QTOF	splash10-0601-0093000000-1abaaf43e0d70f316624	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Negative-QTOF	splash10-0ab9-0091000000-e4fe010c6ed57c8ce4f1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 10V, Negative-QTOF	splash10-014i-0009000000-062ad2a35e11d303cf23	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Negative-QTOF	splash10-014i-0009000000-4f15395cbd12cf9308a0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Negative-QTOF	splash10-014i-3059000000-ecaac400571ca670ba51	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 10V, Positive-QTOF	splash10-00xr-0095000000-f5b39e03f542c252d9d4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 20V, Positive-QTOF	splash10-0ar3-0192000000-43f487add55056118e00	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Grandiflorolic acid 40V, Positive-QTOF	splash10-0670-2930000000-eb189dd440146f16ff22	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015899

KNApSAcK ID

C00022936

Chemspider ID

383411

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

433554

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1858221

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 Grandiflorolic acid (HMDB0036930)

MOL for HMDB0036930 (Grandiflorolic acid)

3D MOL for HMDB0036930 (Grandiflorolic acid)

3D SDF for HMDB0036930 (Grandiflorolic acid)

3D-SDF for HMDB0036930 (Grandiflorolic acid)

PDB for HMDB0036930 (Grandiflorolic acid)

3D PDB for HMDB0036930 (Grandiflorolic acid)

SMILES for HMDB0036930 (Grandiflorolic acid)

INCHI for HMDB0036930 (Grandiflorolic acid)

Structure for HMDB0036930 (Grandiflorolic acid)

3D Structure for HMDB0036930 (Grandiflorolic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra