Hmdb loader

Showing metabocard for ent-16beta-Methoxy-19-kauranoic acid (HMDB0036302)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:25:52 UTC
Update Date2022-03-07 02:54:51 UTC
HMDB IDHMDB0036302
Secondary Accession Numbers
  • HMDB36302
Metabolite Identification
Common Nameent-16beta-Methoxy-19-kauranoic acid
Descriptionent-16beta-Methoxy-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-16beta-Methoxy-19-kauranoic acid.
Structure
Data?1563862853
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)


  Mrv0541 05061309032D          

 24 27  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
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    0.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    2.7993    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
    3.5456    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
    1.9121    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
    0.7383    2.0342    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
    2.1836    1.0613    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
    0.1409    1.3963    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
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    2.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993    2.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 16  7  1  0  0  0  0
 18  1  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  2  1  0  0  0  0
 19 10  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  3  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  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
 24  4  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
Download

3D MOL for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)

HMDB0036302
     RDKit          3D
ent-16beta-Methoxy-19-kauranoic acid
 58 61  0  0  0  0  0  0  0  0999 V2000
    4.8789    0.8562    1.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5371    0.5459    2.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1222   -0.1780    0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9175   -1.4763    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664   -0.5804    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -0.4780   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538   -1.6746   -0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291   -1.7770   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.5447    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444   -0.6866    0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358   -2.0187   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4673   -0.7762    1.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704   -0.7562    2.8882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8221   -0.8884    2.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.3711   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3661    0.9370   -1.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9117    0.8108   -1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093    0.7487   -0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    1.8837    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    0.7739   -0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    1.9163    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529    1.8965   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806    0.5534   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -0.4129   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710    1.4564    2.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    1.4242    0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5228   -0.0510    1.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916   -1.3244    0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737   -1.7823    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -2.3193    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720   -0.0033    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696   -1.6604    1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -1.6753   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771   -2.5792   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580   -2.1983   -1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0097   -2.5757    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1404   -0.5061    1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5933   -2.1166    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6667   -1.9450   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046   -2.8816    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4886   -0.1660    1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9080   -0.0725   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2016    1.1594    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701    0.4953   -2.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6639    2.0212   -1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6908   -0.0779   -2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    1.6824   -2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    1.5309    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8268    2.6131    0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    2.5429    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.9900   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6951    2.8532   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    1.9113    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    2.3581   -1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810    2.5497    0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    0.6439   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.0339   -2.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8777   -1.3765   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  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  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23  3  1  0
 20  6  1  0
 24  6  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
M  END
Download

3D SDF for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)


  Mrv0541 05061309032D          

 24 27  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
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    0.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    2.7993    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
    3.5456    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
    1.9121    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
    0.7383    2.0342    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
    2.1836    1.0613    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
    0.1409    1.3963    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
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    2.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993    2.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 16  7  1  0  0  0  0
 18  1  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  2  1  0  0  0  0
 19 10  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  3  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  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
 24  4  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036302

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1(C)CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O3/c1-18-9-5-10-19(2,17(22)23)15(18)8-11-21-12-14(6-7-16(18)21)20(3,13-21)24-4/h14-16H,5-13H2,1-4H3,(H,22,23)

> <INCHI_KEY>
VYVVNCBNYVCVGC-UHFFFAOYSA-N

> <FORMULA>
C21H34O3

> <MOLECULAR_WEIGHT>
334.4929

> <EXACT_MASS>
334.250794954

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.0880622077498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
4.483395854000002

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.622419248903006

> <JCHEM_PKA_STRONGEST_BASIC>
-4.144503773480418

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
94.01939999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.79e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)

HMDB0036302
     RDKit          3D
ent-16beta-Methoxy-19-kauranoic acid
 58 61  0  0  0  0  0  0  0  0999 V2000
    4.8789    0.8562    1.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5371    0.5459    2.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1222   -0.1780    0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9175   -1.4763    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664   -0.5804    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -0.4780   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538   -1.6746   -0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291   -1.7770   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.5447    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444   -0.6866    0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358   -2.0187   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4673   -0.7762    1.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704   -0.7562    2.8882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8221   -0.8884    2.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.3711   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3661    0.9370   -1.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9117    0.8108   -1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093    0.7487   -0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    1.8837    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    0.7739   -0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    1.9163    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529    1.8965   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806    0.5534   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -0.4129   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2710    1.4564    2.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    1.4242    0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5228   -0.0510    1.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916   -1.3244    0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737   -1.7823    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -2.3193    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720   -0.0033    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696   -1.6604    1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -1.6753   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771   -2.5792   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580   -2.1983   -1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0097   -2.5757    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1404   -0.5061    1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5933   -2.1166    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6667   -1.9450   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046   -2.8816    0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4886   -0.1660    1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9080   -0.0725   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2016    1.1594    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701    0.4953   -2.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6639    2.0212   -1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6908   -0.0779   -2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    1.6824   -2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    1.5309    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8268    2.6131    0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    2.5429    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740    0.9900   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6951    2.8532   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    1.9113    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    2.3581   -1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810    2.5497    0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    0.6439   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.0339   -2.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8777   -1.3765   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  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  2  0
 12 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23  3  1  0
 20  6  1  0
 24  6  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
M  END
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PDB for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)

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      -1.000   1.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.241   5.225   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.129   1.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.722   0.398   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.099   4.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.618   1.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.628   2.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.045   1.193   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       4.076   1.981   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       0.263   2.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.933   3.166   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.905   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
HETATM   24  O   UNK     0      -0.745   3.770   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   24                                                            
CONECT    5    9   10                                                       
CONECT    6    7   14                                                       
CONECT    7    6   16                                                       
CONECT    8   11   15                                                       
CONECT    9    5   18                                                       
CONECT   10    5   19                                                       
CONECT   11    8   21                                                       
CONECT   12   14   21                                                       
CONECT   13   20   21                                                       
CONECT   14    6   12   20                                                  
CONECT   15    8   18   19                                                  
CONECT   16    7   18   21                                                  
CONECT   17   19   22   23                                                  
CONECT   18    1    9   15   16                                             
CONECT   19    2   10   15   17                                             
CONECT   20    3   13   14   24                                             
CONECT   21   11   12   13   16                                             
CONECT   22   17                                                            
CONECT   23   17                                                            
CONECT   24    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END
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3D PDB for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)

COMPND    HMDB0036302
HETATM    1  C1  UNL     1       4.879   0.856   1.878  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.537   0.546   2.040  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.122  -0.178   0.958  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.917  -1.476   0.806  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.666  -0.580   1.014  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.099  -0.478  -0.352  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.354  -1.675  -0.818  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.029  -1.777  -0.290  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.583  -0.545   0.350  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.044  -0.687   0.488  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.536  -2.019  -0.115  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.467  -0.776   1.919  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.670  -0.756   2.888  1.00  0.00           O  
HETATM   14  O3  UNL     1      -4.822  -0.888   2.193  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.897   0.371  -0.140  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.366   0.937  -1.409  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.912   0.811  -1.612  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.109   0.749  -0.300  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.606   1.884   0.545  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.324   0.774  -0.629  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.096   1.916   0.031  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.553   1.897  -0.345  1.00  0.00           C  
HETATM   23  C20 UNL     1       3.181   0.553  -0.357  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.364  -0.413  -1.226  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.271   1.456   2.746  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.112   1.424   0.966  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.523  -0.051   1.853  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.692  -1.324   0.031  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.374  -1.782   1.776  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.267  -2.319   0.495  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.172  -0.003   1.793  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.570  -1.660   1.333  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.364  -1.675  -1.948  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.977  -2.579  -0.554  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.658  -2.198  -1.101  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.010  -2.576   0.511  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.140  -0.506   1.391  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.593  -2.117   0.278  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.667  -1.945  -1.206  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.005  -2.882   0.262  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.489  -0.166   1.928  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.908  -0.073  -0.408  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.202   1.159   0.610  1.00  0.00           H  
HETATM   44  H20 UNL     1      -3.870   0.495  -2.321  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.664   2.021  -1.457  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.691  -0.078  -2.244  1.00  0.00           H  
HETATM   47  H23 UNL     1      -1.500   1.682  -2.163  1.00  0.00           H  
HETATM   48  H24 UNL     1      -2.029   1.531   1.528  1.00  0.00           H  
HETATM   49  H25 UNL     1      -0.827   2.613   0.860  1.00  0.00           H  
HETATM   50  H26 UNL     1      -2.350   2.543   0.006  1.00  0.00           H  
HETATM   51  H27 UNL     1       0.474   0.990  -1.733  1.00  0.00           H  
HETATM   52  H28 UNL     1       0.695   2.853  -0.450  1.00  0.00           H  
HETATM   53  H29 UNL     1       1.049   1.911   1.117  1.00  0.00           H  
HETATM   54  H30 UNL     1       2.722   2.358  -1.344  1.00  0.00           H  
HETATM   55  H31 UNL     1       3.081   2.550   0.379  1.00  0.00           H  
HETATM   56  H32 UNL     1       4.208   0.644  -0.721  1.00  0.00           H  
HETATM   57  H33 UNL     1       2.124   0.034  -2.204  1.00  0.00           H  
HETATM   58  H34 UNL     1       2.878  -1.377  -1.272  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    5   23
CONECT    4   28   29   30
CONECT    5    6   31   32
CONECT    6    7   20   24
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   18   37
CONECT   10   11   12   15
CONECT   11   38   39   40
CONECT   12   13   13   14
CONECT   14   41
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   46   47
CONECT   18   19   20
CONECT   19   48   49   50
CONECT   20   21   51
CONECT   21   22   52   53
CONECT   22   23   54   55
CONECT   23   24   56
CONECT   24   57   58
END
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SMILES for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)

COC1(C)CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O
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INCHI for HMDB0036302 (ent-16beta-Methoxy-19-kauranoic acid)

InChI=1S/C21H34O3/c1-18-9-5-10-19(2,17(22)23)15(18)8-11-21-12-14(6-7-16(18)21)20(3,13-21)24-4/h14-16H,5-13H2,1-4H3,(H,22,23)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
ent-16b-Methoxy-19-kauranoateGenerator
ent-16b-Methoxy-19-kauranoic acidGenerator
ent-16beta-Methoxy-19-kauranoateGenerator
ent-16Β-methoxy-19-kauranoateGenerator
ent-16Β-methoxy-19-kauranoic acidGenerator
14-Methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylateGenerator
Chemical FormulaC21H34O3
Average Molecular Weight334.4929
Monoisotopic Molecular Weight334.250794954
IUPAC Name14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
Traditional Name14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid
CAS Registry Number38308-35-9
SMILES
COC1(C)CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O
InChI Identifier
InChI=1S/C21H34O3/c1-18-9-5-10-19(2,17(22)23)15(18)8-11-21-12-14(6-7-16(18)21)20(3,13-21)24-4/h14-16H,5-13H2,1-4H3,(H,22,23)
InChI KeyVYVVNCBNYVCVGC-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative Parents
Substituents
  • Kaurane diterpenoid
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point216 - 219 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00058 g/LALOGPS
logP4.33ALOGPS
logP4.48ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability39.09 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.7431661259
DarkChem[M-H]-175.40131661259
DeepCCS[M-2H]-217.53330932474
DeepCCS[M+Na]+193.09830932474
AllCCS[M+H]+184.732859911
AllCCS[M+H-H2O]+182.032859911
AllCCS[M+NH4]+187.132859911
AllCCS[M+Na]+187.832859911
AllCCS[M-H]-188.232859911
AllCCS[M+Na-2H]-188.732859911
AllCCS[M+HCOO]-189.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.8.45 minutes32390414
Predicted by Siyang on May 30, 202219.3691 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.56 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2766.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid497.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid236.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid216.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid556.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid820.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid907.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)116.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1550.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid522.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1625.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid600.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid468.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate431.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA522.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water9.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ent-16beta-Methoxy-19-kauranoic acidCOC1(C)CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O3120.8Standard polar33892256
ent-16beta-Methoxy-19-kauranoic acidCOC1(C)CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O2427.2Standard non polar33892256
ent-16beta-Methoxy-19-kauranoic acidCOC1(C)CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O2595.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
ent-16beta-Methoxy-19-kauranoic acid,1TMS,isomer #1COC1(C)CC23CCC4C(C)(C(=O)O[Si](C)(C)C)CCCC4(C)C2CCC1C32480.6Semi standard non polar33892256
ent-16beta-Methoxy-19-kauranoic acid,1TBDMS,isomer #1COC1(C)CC23CCC4C(C)(C(=O)O[Si](C)(C)C(C)(C)C)CCCC4(C)C2CCC1C32769.0Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015170
KNApSAcK IDNot Available
Chemspider ID433824
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound495571
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.