NP-MRD: Showing NP-Card for 17-chloro-13,16beta-dihydroxy-ent-kauran-19-al (NP0027495)

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Record Information

Version

2.0

Created at

2021-06-19 19:38:13 UTC

Updated at

2021-06-29 23:53:39 UTC

NP-MRD ID

NP0027495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-chloro-13,16beta-dihydroxy-ent-kauran-19-al

Provided By

JEOL Database JEOL Logo

Description

17-chloro-13,16beta-dihydroxy-ent-kauran-19-al is found in Bruguiera gymnorrhiza. 17-chloro-13,16beta-dihydroxy-ent-kauran-19-al was first documented in 2004 (Han, L., et al.). Based on a literature review very few articles have been published on 17-chloro-13,16beta-dihydroxy-ent-kauran-19-al.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121383D          

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     RDKit          3D

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  Mrv1652306192121383D          

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    2.3404    0.2807    1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559    2.0303    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    1.2268   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    2.0941   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709    0.6951   -1.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7061    0.9314   -2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -0.8433   -3.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.1415   -4.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517   -0.9185   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -3.8325   -2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -3.2755   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -3.2908    0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1580   -1.9315    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590   -1.1501   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.5788    0.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.0711   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -1.8043    0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0  0  0  0
 13 24  1  0  0  0  0
 21 22  1  0  0  0  0
  4  5  1  0  0  0  0
  4  3  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2 23  1  0  0  0  0
 10 11  1  0  0  0  0
  6  8  1  1  0  0  0
 11 12  1  0  0  0  0
 17 18  1  0  0  0  0
 10 38  1  6  0  0  0
 21 19  1  0  0  0  0
 15 17  1  0  0  0  0
 13 12  1  1  0  0  0
  2  1  1  1  0  0  0
 23 13  1  0  0  0  0
 13 14  1  0  0  0  0
 19 15  1  0  0  0  0
  6 10  1  0  0  0  0
 19 20  1  6  0  0  0
 15 14  1  0  0  0  0
  2  3  1  0  0  0  0
  8 37  1  0  0  0  0
  2 10  1  0  0  0  0
  8  9  2  0  0  0  0
 19 24  1  0  0  0  0
 15 16  1  6  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 23 53  1  1  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 20 48  1  0  0  0  0
 16 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C([H])([H])Cl)C([H])([H])[C@]23C([H])([H])[C@@]1(O[H])C([H])([H])C([H])([H])[C@@]2([H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@](C([H])=O)(C([H])([H])[H])[C@@]1([H])C([H])([H])C3([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H31ClO3/c1-16(13-22)6-3-7-17(2)14(16)4-8-18-10-19(23,9-5-15(17)18)20(24,11-18)12-21/h13-15,23-24H,3-12H2,1-2H3/t14-,15+,16+,17-,18+,19+,20-/m1/s1

> <INCHI_KEY>
DTMIPKXLCMUODX-KOGWCRERSA-N

> <FORMULA>
C20H31ClO3

> <MOLECULAR_WEIGHT>
354.92

> <EXACT_MASS>
354.1961726

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.85727139925853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10R,13S,14S)-14-(chloromethyl)-13,14-dihydroxy-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.9079889523333327

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.459585429994242

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.870299524332935

> <JCHEM_PKA_STRONGEST_BASIC>
-3.400851235555997

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
94.38859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10R,13S,14S)-14-(chloromethyl)-13,14-dihydroxy-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    0.2645   -1.5118    2.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4355   -0.2293    2.0547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7976   -0.1062    2.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658    0.2023    4.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185    1.4401    4.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5655    1.4184    3.8752 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1906    2.8195    4.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5280    0.4670    4.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104   -0.0675    5.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3885    1.0765    2.3587 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6824    1.1263    1.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568    1.1632    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204   -0.0281   -0.4440 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0213    0.2302   -1.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0402   -1.1416   -2.6316 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2610   -1.4697   -3.1338 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0306   -1.1642   -3.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534    0.0076   -5.0908 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4477   -2.1400   -1.5088 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1434   -3.2732   -2.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -2.6307   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5378   -1.5088    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.2842    0.4882 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3720   -1.2897   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3051   -1.5805    2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -1.5854    3.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541   -2.4124    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -1.0271    2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981    0.6903    2.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -0.6586    4.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    0.3612    4.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7113    1.5676    5.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3812    2.3154    4.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    3.5786    3.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430    2.8488    3.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1659    3.1202    5.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980    0.3065    4.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298    1.9042    1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404    0.2807    1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559    2.0303    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    1.2268   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    2.0941   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709    0.6951   -1.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7061    0.9314   -2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -0.8433   -3.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.1415   -4.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517   -0.9185   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -3.8325   -2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -3.2755   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -3.2908    0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1580   -1.9315    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590   -1.1501   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.5788    0.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.0711   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -1.8043    0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 13 24  1  0
 21 22  1  0
  4  5  1  0
  4  3  1  0
  5  6  1  0
  6  7  1  0
  2 23  1  0
 10 11  1  0
  6  8  1  1
 11 12  1  0
 17 18  1  0
 10 38  1  6
 21 19  1  0
 15 17  1  0
 13 12  1  1
  2  1  1  1
 23 13  1  0
 13 14  1  0
 19 15  1  0
  6 10  1  0
 19 20  1  6
 15 14  1  0
  2  3  1  0
  8 37  1  0
  2 10  1  0
  8  9  2  0
 19 24  1  0
 15 16  1  6
 17 46  1  0
 17 47  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  3 28  1  0
  3 29  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 23 53  1  1
 22 51  1  0
 22 52  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
 24 54  1  0
 24 55  1  0
 21 49  1  0
 21 50  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 14 43  1  0
 14 44  1  0
 20 48  1  0
 16 45  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.265  -1.512   2.557  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.436  -0.229   2.055  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.798  -0.106   2.808  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.666   0.202   4.298  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.819   1.440   4.564  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.566   1.418   3.875  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.191   2.820   4.063  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.528   0.467   4.584  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.310  -0.068   5.667  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.389   1.077   2.359  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.682   1.126   1.526  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.357   1.163   0.037  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.520  -0.028  -0.444  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.021   0.230  -1.908  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.040  -1.142  -2.632  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.261  -1.470  -3.134  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.031  -1.164  -3.818  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       0.553   0.008  -5.091  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       0.448  -2.140  -1.509  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.143  -3.273  -2.012  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.721  -2.631  -0.635  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.538  -1.509   0.009  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.716  -0.284   0.488  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.372  -1.290  -0.645  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.305  -1.581   2.242  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.280  -1.585   3.646  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.254  -2.412   2.219  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.382  -1.027   2.709  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.398   0.690   2.348  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.255  -0.659   4.835  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.667   0.361   4.717  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.711   1.568   5.649  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.381   2.315   4.210  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.649   3.579   3.489  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.243   2.849   3.761  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.166   3.120   5.118  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.498   0.307   4.083  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.230   1.904   1.971  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.340   0.281   1.747  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.256   2.030   1.752  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.294   1.227  -0.531  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.813   2.094  -0.175  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.971   0.695  -1.927  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.706   0.931  -2.400  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.452  -0.843  -3.858  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.030  -2.142  -4.309  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.052  -0.919  -3.514  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.483  -3.833  -2.462  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.389  -3.276  -1.221  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.322  -3.291   0.146  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.158  -1.932   0.804  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.259  -1.150  -0.738  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.381   0.579   0.318  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.309  -1.071  -1.173  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.667  -1.804   0.268  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2   23    1    3   10                                             
CONECT    3    4    2   28   29                                             
CONECT    4    5    3   30   31                                             
CONECT    5    4    6   32   33                                             
CONECT    6    5    7    8   10                                             
CONECT    7    6   34   35   36                                             
CONECT    8    6   37    9                                                  
CONECT    9    8                                                            
CONECT   10   11   38    6    2                                             
CONECT   11   10   12   39   40                                             
CONECT   12   11   13   41   42                                             
CONECT   13   24   12   23   14                                             
CONECT   14   13   15   43   44                                             
CONECT   15   17   19   14   16                                             
CONECT   16   15   45                                                       
CONECT   17   18   15   46   47                                             
CONECT   18   17                                                            
CONECT   19   21   15   20   24                                             
CONECT   20   19   48                                                       
CONECT   21   22   19   49   50                                             
CONECT   22   23   21   51   52                                             
CONECT   23   22    2   13   53                                             
CONECT   24   13   19   54   55                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
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   -0.4355   -0.2293    2.0547 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.2541   -2.4124    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -1.0271    2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981    0.6903    2.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -0.6586    4.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6673    0.3612    4.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7113    1.5676    5.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6485    3.5786    3.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430    2.8488    3.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1659    3.1202    5.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980    0.3065    4.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298    1.9042    1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404    0.2807    1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559    2.0303    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    1.2268   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    2.0941   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7061    0.9314   -2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -0.8433   -3.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -2.1415   -4.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517   -0.9185   -3.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -3.8325   -2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -3.2755   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -3.2908    0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1580   -1.9315    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590   -1.1501   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.5788    0.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -1.0711   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -1.8043    0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2 23  1  0
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  6  8  1  1
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 15 17  1  0
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  2  1  1  1
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  2 10  1  0
  8  9  2  0
 19 24  1  0
 15 16  1  6
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  4 30  1  0
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 23 53  1  1
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  7 34  1  0
  7 35  1  0
  7 36  1  0
 24 54  1  0
 24 55  1  0
 21 49  1  0
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  1 25  1  0
  1 26  1  0
  1 27  1  0
 14 43  1  0
 14 44  1  0
 20 48  1  0
 16 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
17-Chloro-13,16b-dihydroxy-ent-kauran-19-al	Generator
17-Chloro-13,16β-dihydroxy-ent-kauran-19-al	Generator

Chemical Formula

C₂₀H₃₁ClO₃

Average Mass

354.9200 Da

Monoisotopic Mass

354.19617 Da

IUPAC Name

(1S,4S,5R,9S,10R,13S,14S)-14-(chloromethyl)-13,14-dihydroxy-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

Traditional Name

(1S,4S,5R,9S,10R,13S,14S)-14-(chloromethyl)-13,14-dihydroxy-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C([H])([H])Cl)C([H])([H])[C@]23C([H])([H])[C@@]1(O[H])C([H])([H])C([H])([H])[C@@]2([H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@](C([H])=O)(C([H])([H])[H])[C@@]1([H])C([H])([H])C3([H])[H]

InChI Identifier

InChI=1S/C20H31ClO3/c1-16(13-22)6-3-7-17(2)14(16)4-8-18-10-19(23,9-5-15(17)18)20(24,11-18)12-21/h13-15,23-24H,3-12H2,1-2H3/t14-,15+,16+,17-,18+,19+,20-/m1/s1

InChI Key

DTMIPKXLCMUODX-KOGWCRERSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Bruguiera gymnorhiza	JEOL database	Han, L., et al, J. Nat. Prod. 67, 1620 (2004)

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
Tertiary alcohol
1,2-diol
Chlorohydrin
Halohydrin
Organochloride
Organohalogen compound
Aldehyde
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Alkyl chloride
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	3.01	ALOGPS
logP	2.91	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.39 m³·mol⁻¹	ChemAxon
Polarizability	38.86 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

10208610

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21589750

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han, L., et al. (2004). Han, L., et al, J. Nat. Prod. 67, 1620 (2004). J. Nat. Prod..

Showing NP-Card for 17-chloro-13,16beta-dihydroxy-ent-kauran-19-al (NP0027495)

MOL for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

3D MOL for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

3D SDF for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

3D-SDF for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

PDB for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

3D PDB for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

SMILES for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

INCHI for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

Structure for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)

3D Structure for NP0027495 (17-chloro-13,16beta-dihydroxy-ent-kauran-19-al)