NP-MRD: Showing NP-Card for 7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione (NP0043024)

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Record Information

Version

1.0

Created at

2021-06-21 00:32:29 UTC

Updated at

2021-06-30 00:18:28 UTC

NP-MRD ID

NP0043024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione

Provided By

JEOL Database JEOL Logo

Description

CHEMBL3092693 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. 7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione is found in Salvia cavaleriei. It was first documented in 2013 (Zheng, H., et al.). Based on a literature review very few articles have been published on CHEMBL3092693.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102323D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102323D          

 57 60  0  0  0  0            999 V2000
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    3.9212   -4.7039   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -4.9162    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005   -3.8376   -2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361   -0.3902   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -3.9279   -4.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0357   -3.3798   -3.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -4.9389   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776   -2.8077   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0202   -3.0557    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -1.3338   -3.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    0.1286   -3.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -1.0193   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775    1.3856   -3.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241    0.4656   -4.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0646    2.8787   -4.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    1.9751   -4.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    4.2698   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272    2.8968    0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    3.4968   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501    1.5793   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904    3.1013   -1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    1.6198   -2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1416    1.4049   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -0.3097   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.8199    0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -0.2938    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7241   -1.0148    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0  0  0  0
 19 21  1  0  0  0  0
 24 53  1  1  0  0  0
 15  8  1  0  0  0  0
  8 34  1  1  0  0  0
 24 25  1  0  0  0  0
 12  4  1  0  0  0  0
 25 26  1  0  0  0  0
  7  5  1  1  0  0  0
 26  7  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  1  0  0  0  0
  8  7  1  0  0  0  0
  4  3  1  0  0  0  0
 21 24  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 26 27  1  0  0  0  0
 15 24  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 18 19  1  0  0  0  0
  5  6  2  0  0  0  0
 18 17  1  0  0  0  0
  9 10  2  0  0  0  0
  8  9  1  0  0  0  0
 12 37  1  6  0  0  0
  7 13  1  0  0  0  0
 19 20  2  0  0  0  0
 13 12  1  0  0  0  0
  3  2  1  0  0  0  0
 12 11  1  0  0  0  0
  2  1  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 26 56  1  1  0  0  0
 13 38  1  6  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
  4 33  1  6  0  0  0
 14 39  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 27 57  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])C([H])([H])C(=O)[C@]3([H])[C@@]1(C(=O)[C@@]2([H])C([H])([H])OC([H])([H])[H])[C@]([H])(O[H])C([H])([H])[C@]1([H])C(C(=O)C([H])([H])C([H])([H])[C@@]31C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O6/c1-19(2)13-8-15(24)21-16(20(13,3)6-5-14(19)23)12(22)7-10(17(21)25)11(9-27-4)18(21)26/h10-11,13,15-17,24-25H,5-9H2,1-4H3/t10-,11-,13+,15+,16-,17+,20+,21-/m0/s1

> <INCHI_KEY>
LNXQFRXVRSEEBN-PQWDXQMVSA-N

> <FORMULA>
C21H30O6

> <MOLECULAR_WEIGHT>
378.465

> <EXACT_MASS>
378.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.18945822575503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,9R,10S,13S,14R,16R)-2,16-dihydroxy-14-(methoxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,11,15-trione

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
0.9406208353333328

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.667075488467614

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.801689660290663

> <JCHEM_PKA_STRONGEST_BASIC>
-3.053531190272495

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
97.42839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,9R,10S,13S,14R,16R)-2,16-dihydroxy-14-(methoxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,11,15-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
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    2.9256   -6.1593   -1.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5372   -1.9326   -0.3240 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1941   -1.7574   -0.9965 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2913   -0.9562   -2.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5264   -1.8883   -3.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.4607   -4.5759 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0617   -3.3318   -3.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335   -3.9057   -2.0515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3095   -3.0142   -1.1214 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0966   -3.7170    0.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.1242   -2.5716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1893   -0.5592   -2.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    1.0342   -3.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    2.2493   -3.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419    3.0744   -2.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    4.3025   -2.7649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    2.3454   -1.3790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3547    3.2991   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704    2.1359   -1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082    1.0364   -1.2909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1692    0.1905   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -0.8370    0.2079 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5654   -1.5876    1.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145   -7.0801    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -7.2806    0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2207   -8.1579   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212   -4.7039   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -4.9162    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005   -3.8376   -2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361   -0.3902   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -3.9279   -4.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0357   -3.3798   -3.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -4.9389   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776   -2.8077   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0202   -3.0557    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -1.3338   -3.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    0.1286   -3.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -1.0193   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775    1.3856   -3.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241    0.4656   -4.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0646    2.8787   -4.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    1.9751   -4.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    4.2698   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272    2.8968    0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    3.4968   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501    1.5793   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904    3.1013   -1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    1.6198   -2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1416    1.4049   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -0.3097   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.8199    0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -0.2938    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7241   -1.0148    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
 19 21  1  0
 24 53  1  1
 15  8  1  0
  8 34  1  1
 24 25  1  0
 12  4  1  0
 25 26  1  0
  7  5  1  1
 26  7  1  0
 13 14  1  0
  4  5  1  0
  8  7  1  0
  4  3  1  0
 21 24  1  0
 15 16  1  6
 15 17  1  0
 26 27  1  0
 15 24  1  0
 21 22  1  1
 21 23  1  0
 18 19  1  0
  5  6  2  0
 18 17  1  0
  9 10  2  0
  8  9  1  0
 12 37  1  6
  7 13  1  0
 19 20  2  0
 13 12  1  0
  3  2  1  0
 12 11  1  0
  2  1  1  0
 18 45  1  0
 18 46  1  0
 17 43  1  0
 17 44  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  1
 13 38  1  6
 11 35  1  0
 11 36  1  0
  4 33  1  6
 14 39  1  0
  3 31  1  0
  3 32  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 27 57  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.224  -7.220  -0.228  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.926  -6.159  -1.127  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.922  -4.894  -0.462  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.571  -3.822  -1.482  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.554  -2.451  -0.840  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.537  -1.933  -0.324  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.194  -1.757  -0.997  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.291  -0.956  -2.335  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.526  -1.888  -3.540  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.037  -1.461  -4.576  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.062  -3.332  -3.467  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.133  -3.906  -2.051  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.310  -3.014  -1.121  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.097  -3.717   0.093  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.156   0.124  -2.572  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.189  -0.559  -2.900  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.545   1.034  -3.772  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.353   2.249  -3.956  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.442   3.074  -2.697  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.361   4.303  -2.765  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.752   2.345  -1.379  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.355   3.299  -0.221  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.270   2.136  -1.285  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.108   1.036  -1.291  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.169   0.191  -0.035  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.937  -0.837   0.208  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.565  -1.588   1.367  0.00  0.00           O+0
HETATM   28  H   UNK     0       4.215  -7.080   0.215  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.464  -7.281   0.558  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.221  -8.158  -0.789  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.921  -4.704  -0.051  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.218  -4.916   0.377  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.301  -3.838  -2.300  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.236  -0.390  -2.269  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.693  -3.928  -4.136  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.036  -3.380  -3.846  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.769  -4.939  -2.055  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.678  -2.808  -1.534  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.020  -3.056   0.817  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.067  -1.334  -3.663  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.925   0.129  -3.318  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.658  -1.019  -2.030  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.577   1.386  -3.640  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.524   0.466  -4.708  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.065   2.879  -4.751  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.364   1.975  -4.268  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.858   4.270  -0.308  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.627   2.897   0.759  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.724   3.497  -0.222  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.550   1.579  -0.385  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.790   3.101  -1.242  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.686   1.620  -2.150  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.142   1.405  -1.174  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.142  -0.310  -0.086  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.229   0.820   0.859  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.856  -0.294   0.463  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.724  -1.015   2.143  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   31   32                                             
CONECT    4   12    5    3   33                                             
CONECT    5    7    4    6                                                  
CONECT    6    5                                                            
CONECT    7    5   26    8   13                                             
CONECT    8   15   34    7    9                                             
CONECT    9   11   10    8                                                  
CONECT   10    9                                                            
CONECT   11    9   12   35   36                                             
CONECT   12    4   37   13   11                                             
CONECT   13   14    7   12   38                                             
CONECT   14   13   39                                                       
CONECT   15    8   16   17   24                                             
CONECT   16   15   40   41   42                                             
CONECT   17   15   18   43   44                                             
CONECT   18   19   17   45   46                                             
CONECT   19   21   18   20                                                  
CONECT   20   19                                                            
CONECT   21   19   24   22   23                                             
CONECT   22   21   47   48   49                                             
CONECT   23   21   50   51   52                                             
CONECT   24   53   25   21   15                                             
CONECT   25   24   26   54   55                                             
CONECT   26   25    7   27   56                                             
CONECT   27   26   57                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    8                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
    3.2236   -7.2200   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256   -6.1593   -1.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217   -4.8941   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706   -3.8217   -1.4821 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5540   -2.4508   -0.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -1.9326   -0.3240 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1941   -1.7574   -0.9965 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2913   -0.9562   -2.3348 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5264   -1.8883   -3.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.4607   -4.5759 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0617   -3.3318   -3.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335   -3.9057   -2.0515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3095   -3.0142   -1.1214 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0966   -3.7170    0.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.1242   -2.5716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1893   -0.5592   -2.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    1.0342   -3.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527    2.2493   -3.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419    3.0744   -2.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    4.3025   -2.7649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    2.3454   -1.3790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3547    3.2991   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2704    2.1359   -1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082    1.0364   -1.2909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1692    0.1905   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -0.8370    0.2079 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5654   -1.5876    1.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145   -7.0801    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -7.2806    0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2207   -8.1579   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212   -4.7039   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -4.9162    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005   -3.8376   -2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361   -0.3902   -2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -3.9279   -4.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0357   -3.3798   -3.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -4.9389   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776   -2.8077   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0202   -3.0557    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -1.3338   -3.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    0.1286   -3.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -1.0193   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5775    1.3856   -3.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241    0.4656   -4.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0646    2.8787   -4.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    1.9751   -4.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    4.2698   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272    2.8968    0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    3.4968   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501    1.5793   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904    3.1013   -1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    1.6198   -2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1416    1.4049   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -0.3097   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294    0.8199    0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -0.2938    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7241   -1.0148    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
 19 21  1  0
 24 53  1  1
 15  8  1  0
  8 34  1  1
 24 25  1  0
 12  4  1  0
 25 26  1  0
  7  5  1  1
 26  7  1  0
 13 14  1  0
  4  5  1  0
  8  7  1  0
  4  3  1  0
 21 24  1  0
 15 16  1  6
 15 17  1  0
 26 27  1  0
 15 24  1  0
 21 22  1  1
 21 23  1  0
 18 19  1  0
  5  6  2  0
 18 17  1  0
  9 10  2  0
  8  9  1  0
 12 37  1  6
  7 13  1  0
 19 20  2  0
 13 12  1  0
  3  2  1  0
 12 11  1  0
  2  1  1  0
 18 45  1  0
 18 46  1  0
 17 43  1  0
 17 44  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  1
 13 38  1  6
 11 35  1  0
 11 36  1  0
  4 33  1  6
 14 39  1  0
  3 31  1  0
  3 32  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 27 57  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₆

Average Mass

378.4650 Da

Monoisotopic Mass

378.20424 Da

IUPAC Name

(1R,2R,4S,9R,10S,13S,14R,16R)-2,16-dihydroxy-14-(methoxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,11,15-trione

Traditional Name

(1R,2R,4S,9R,10S,13S,14R,16R)-2,16-dihydroxy-14-(methoxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-6,11,15-trione

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]2([H])C([H])([H])C(=O)[C@]3([H])[C@@]1(C(=O)[C@@]2([H])C([H])([H])OC([H])([H])[H])[C@]([H])(O[H])C([H])([H])[C@]1([H])C(C(=O)C([H])([H])C([H])([H])[C@@]31C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H30O6/c1-19(2)13-8-15(24)21-16(20(13,3)6-5-14(19)23)12(22)7-10(17(21)25)11(9-27-4)18(21)26/h10-11,13,15-17,24-25H,5-9H2,1-4H3/t10-,11-,13+,15+,16-,17+,20+,21-/m0/s1

InChI Key

LNXQFRXVRSEEBN-PQWDXQMVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia cavaleriei	JEOL database	Zheng, H., et al, J. Nat. Prod. 76, 2253 (2013)

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
Cyclic ketone
Secondary alcohol
Ketone
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.2	ALOGPS
logP	0.94	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.43 m³·mol⁻¹	ChemAxon
Polarizability	40.19 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31129903

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76328131

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zheng, H., et al. (2013). Zheng, H., et al, J. Nat. Prod. 76, 2253 (2013). J. Nat. Prod..

Showing NP-Card for 7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione (NP0043024)

MOL for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

3D MOL for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

3D SDF for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

3D-SDF for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

PDB for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

3D PDB for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

SMILES for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

INCHI for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

Structure for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)

3D Structure for NP0043024 (7alpha,14beta-dihydroxy-17alpha-methoxymethyl-ent-kaur-3,11,15-trione)