NP-MRD: Showing NP-Card for 3-epipseurata B (NP0034429)

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Record Information

Version

2.0

Created at

2021-06-20 18:09:41 UTC

Updated at

2021-06-30 00:04:48 UTC

NP-MRD ID

NP0034429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-epipseurata B

Provided By

JEOL Database JEOL Logo

Description

3-Epi-Pseurata B 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. 3-epipseurata B is found in Isodon pharicus. 3-epipseurata B was first documented in 2009 (Zhao, Y., et al.). Based on a literature review very few articles have been published on 3-epi-Pseurata B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120093D          

 55 58  0  0  0  0            999 V2000
   -1.7652   -5.4744   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -4.2908   -1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138   -3.1246   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -3.1898   -0.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796   -1.9120   -0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2475   -1.9851    0.7829 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6022   -3.2907    0.9554 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1063   -3.9918   -0.3228 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4142   -3.5067   -0.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948   -3.8072   -1.5402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0396   -2.3078   -1.7723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5858   -2.1413   -3.0828 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8717   -0.7505    2.7444 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.2215    1.6513    3.2495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9082    1.2408    4.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222    1.9005    1.7791 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4836    2.8114    1.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851    0.5242    1.1037 C   0  0  1  0  0  0  0  0  0  0  0  0
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  5 11  1  0  0  0  0
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  8  7  1  0  0  0  0
 17 19  1  0  0  0  0
 17 18  1  0  0  0  0
 13  6  1  0  0  0  0
 19 20  1  6  0  0  0
 22 23  1  0  0  0  0
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 23 24  1  0  0  0  0
  6 28  1  1  0  0  0
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 10  2  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  1  0  0  0
 19 22  1  0  0  0  0
 11 12  1  0  0  0  0
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 13 14  1  6  0  0  0
  8  9  1  0  0  0  0
 16 17  1  0  0  0  0
 24 25  1  0  0  0  0
  2  3  1  0  0  0  0
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  2  1  2  3  0  0  0
  6  7  1  0  0  0  0
  3  4  2  0  0  0  0
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  8 31  1  1  0  0  0
  7 29  1  0  0  0  0
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  9 32  1  0  0  0  0
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  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
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    1.1063   -3.9918   -0.3228 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4142   -3.5067   -0.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948   -3.8072   -1.5402 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202120093D          

 55 58  0  0  0  0            999 V2000
   -1.7652   -5.4744   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -4.2908   -1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138   -3.1246   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -3.1898   -0.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796   -1.9120   -0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6131   -4.2803   -2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.7463   -1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044   -1.3778   -3.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -1.2928    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668   -0.1279   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    0.3775    0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -1.4560    2.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0308   -1.1600    3.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2413    0.9241    2.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    0.3876    4.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    2.5866    3.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162    1.1622    4.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299    2.7996   -0.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    3.7234    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584    2.2846    1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252    3.6768    2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658    2.2760    2.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247    3.2076    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4624    0.1766    1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    0.8659   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796    1.4728   -0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7327   -0.7072   -0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    0.1916   -2.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  8  1  0  0  0  0
  8  7  1  0  0  0  0
 17 19  1  0  0  0  0
 17 18  1  0  0  0  0
 13  6  1  0  0  0  0
 19 20  1  6  0  0  0
 22 23  1  0  0  0  0
 22 51  1  1  0  0  0
 23 24  1  0  0  0  0
  6 28  1  1  0  0  0
 24  5  1  0  0  0  0
 10  2  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  1  0  0  0
 19 22  1  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 19 21  1  0  0  0  0
 13 22  1  0  0  0  0
 13 14  1  6  0  0  0
  8  9  1  0  0  0  0
 16 17  1  0  0  0  0
 24 25  1  0  0  0  0
  2  3  1  0  0  0  0
 16 15  1  0  0  0  0
  2  1  2  3  0  0  0
  6  7  1  0  0  0  0
  3  4  2  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 17 43  1  1  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 24 54  1  1  0  0  0
 11 34  1  6  0  0  0
 10 33  1  6  0  0  0
  8 31  1  1  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
 18 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 12 35  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
  9 32  1  0  0  0  0
 25 55  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@]2([H])C(=C([H])[H])C(=O)[C@]11[C@]([H])(O[H])C([H])([H])[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1([H])C([H])([H])[C@]2([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-9-15-10(21)7-12-19(4)6-5-13(22)18(2,3)11(19)8-14(23)20(12,16(9)24)17(15)25/h10-15,17,21-23,25H,1,5-8H2,2-4H3/t10-,11+,12-,13-,14+,15+,17+,19+,20-/m0/s1

> <INCHI_KEY>
BRNLPJIEDLXFLS-WEMBNSTNSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.764638806250034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,6S,9R,10S,12S,13R,16R)-2,6,12,16-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.5011478970000005

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.500150230196425

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.840714415720377

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351402986626101

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
92.43159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,6S,9R,10S,12S,13R,16R)-2,6,12,16-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -1.7652   -5.4744   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -4.2908   -1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138   -3.1246   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -3.1898   -0.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796   -1.9120   -0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2475   -1.9851    0.7829 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6022   -3.2907    0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1063   -3.9918   -0.3228 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4142   -3.5067   -0.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948   -3.8072   -1.5402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0396   -2.3078   -1.7723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5858   -2.1413   -3.0828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696   -0.6381    1.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7584   -0.4041    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8717   -0.7505    2.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963    0.5758    3.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    1.6513    3.2495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9082    1.2408    4.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222    1.9005    1.7791 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8589    2.7050    1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836    2.8114    1.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851    0.5242    1.1037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0780    0.6396   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -0.6298   -0.7813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2109   -0.4414   -2.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104   -6.2784   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8066   -5.6581   -1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0572   -2.1062    1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524   -4.0117    1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423   -3.1369    1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -5.0605   -0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -4.0422   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131   -4.2803   -2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.7463   -1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044   -1.3778   -3.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -1.2928    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668   -0.1279   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    0.3775    0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -1.4560    2.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0308   -1.1600    3.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2413    0.9241    2.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    0.3876    4.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    2.5866    3.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162    1.1622    4.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299    2.7996   -0.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    3.7234    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584    2.2846    1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252    3.6768    2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658    2.2760    2.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247    3.2076    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4624    0.1766    1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    0.8659   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796    1.4728   -0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7327   -0.7072   -0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    0.1916   -2.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0
 11 10  1  0
 10  8  1  0
  8  7  1  0
 17 19  1  0
 17 18  1  0
 13  6  1  0
 19 20  1  6
 22 23  1  0
 22 51  1  1
 23 24  1  0
  6 28  1  1
 24  5  1  0
 10  2  1  0
  6  5  1  0
  5  3  1  1
 19 22  1  0
 11 12  1  0
 13 15  1  0
 19 21  1  0
 13 22  1  0
 13 14  1  6
  8  9  1  0
 16 17  1  0
 24 25  1  0
  2  3  1  0
 16 15  1  0
  2  1  2  3
  6  7  1  0
  3  4  2  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
 15 39  1  0
 15 40  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  1
 11 34  1  6
 10 33  1  6
  8 31  1  1
  7 29  1  0
  7 30  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 12 35  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
  9 32  1  0
 25 55  1  0
  1 26  1  0
  1 27  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.765  -5.474  -1.502  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.200  -4.291  -1.251  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.914  -3.125  -0.644  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.038  -3.190  -0.171  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.980  -1.912  -0.608  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.248  -1.985   0.783  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.602  -3.291   0.955  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.106  -3.992  -0.323  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.414  -3.507  -0.625  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.195  -3.807  -1.540  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.040  -2.308  -1.772  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.586  -2.141  -3.083  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.470  -0.638   1.242  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.758  -0.404   0.427  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.872  -0.751   2.744  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.296   0.576   3.382  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.222   1.651   3.249  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.908   1.241   4.027  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.222   1.901   1.779  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.859   2.705   1.030  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.484   2.811   1.808  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.585   0.524   1.104  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.078   0.640  -0.347  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.810  -0.630  -0.781  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.211  -0.441  -2.143  0.00  0.00           O+0
HETATM   26  H   UNK     0      -1.210  -6.278  -1.973  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.807  -5.658  -1.251  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.057  -2.106   1.523  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.052  -4.012   1.467  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.442  -3.137   1.638  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.222  -5.061  -0.102  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.769  -4.042  -1.358  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.613  -4.280  -2.436  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.895  -1.746  -1.768  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.204  -1.378  -3.046  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.392  -1.293   0.425  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.567  -0.128  -0.610  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.391   0.378   0.845  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.700  -1.456   2.874  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.031  -1.160   3.319  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.241   0.924   2.955  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.493   0.388   4.445  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.586   2.587   3.692  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.616   1.162   4.952  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.630   2.800  -0.036  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.927   3.723   1.433  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.858   2.285   1.127  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.325   3.677   2.463  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.366   2.276   2.176  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.725   3.208   0.816  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.462   0.177   1.675  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.265   0.866  -1.044  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.780   1.473  -0.461  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.733  -0.707  -0.192  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.955   0.192  -2.132  0.00  0.00           H+0
CONECT    1    2   26   27                                                  
CONECT    2   10    3    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   11   24    6    3                                             
CONECT    6   13   28    5    7                                             
CONECT    7    8    6   29   30                                             
CONECT    8   10    7    9   31                                             
CONECT    9    8   32                                                       
CONECT   10   11    8    2   33                                             
CONECT   11    5   10   12   34                                             
CONECT   12   11   35                                                       
CONECT   13    6   15   22   14                                             
CONECT   14   13   36   37   38                                             
CONECT   15   13   16   39   40                                             
CONECT   16   17   15   41   42                                             
CONECT   17   19   18   16   43                                             
CONECT   18   17   44                                                       
CONECT   19   17   20   22   21                                             
CONECT   20   19   45   46   47                                             
CONECT   21   19   48   49   50                                             
CONECT   22   23   51   19   13                                             
CONECT   23   22   24   52   53                                             
CONECT   24   23    5   25   54                                             
CONECT   25   24   55                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
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
   -1.7652   -5.4744   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -4.2908   -1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9138   -3.1246   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -3.1898   -0.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796   -1.9120   -0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2475   -1.9851    0.7829 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6022   -3.2907    0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1063   -3.9918   -0.3228 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4142   -3.5067   -0.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948   -3.8072   -1.5402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0396   -2.3078   -1.7723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5858   -2.1413   -3.0828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696   -0.6381    1.2425 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7584   -0.4041    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8717   -0.7505    2.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963    0.5758    3.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    1.6513    3.2495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9082    1.2408    4.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222    1.9005    1.7791 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8589    2.7050    1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836    2.8114    1.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851    0.5242    1.1037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0780    0.6396   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -0.6298   -0.7813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2109   -0.4414   -2.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104   -6.2784   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8066   -5.6581   -1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0572   -2.1062    1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524   -4.0117    1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423   -3.1369    1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -5.0605   -0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -4.0422   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131   -4.2803   -2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.7463   -1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044   -1.3778   -3.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -1.2928    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668   -0.1279   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    0.3775    0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -1.4560    2.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0308   -1.1600    3.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2413    0.9241    2.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    0.3876    4.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    2.5866    3.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162    1.1622    4.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299    2.7996   -0.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    3.7234    1.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584    2.2846    1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252    3.6768    2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658    2.2760    2.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247    3.2076    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4624    0.1766    1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    0.8659   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796    1.4728   -0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7327   -0.7072   -0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    0.1916   -2.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0
 11 10  1  0
 10  8  1  0
  8  7  1  0
 17 19  1  0
 17 18  1  0
 13  6  1  0
 19 20  1  6
 22 23  1  0
 22 51  1  1
 23 24  1  0
  6 28  1  1
 24  5  1  0
 10  2  1  0
  6  5  1  0
  5  3  1  1
 19 22  1  0
 11 12  1  0
 13 15  1  0
 19 21  1  0
 13 22  1  0
 13 14  1  6
  8  9  1  0
 16 17  1  0
 24 25  1  0
  2  3  1  0
 16 15  1  0
  2  1  2  3
  6  7  1  0
  3  4  2  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
 15 39  1  0
 15 40  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  1
 11 34  1  6
 10 33  1  6
  8 31  1  1
  7 29  1  0
  7 30  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 12 35  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
  9 32  1  0
 25 55  1  0
  1 26  1  0
  1 27  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(1R,2R,4S,6S,9R,10S,12S,13R,16R)-2,6,12,16-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

Traditional Name

(1R,2R,4S,6S,9R,10S,12S,13R,16R)-2,6,12,16-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@]2([H])C(=C([H])[H])C(=O)[C@]11[C@]([H])(O[H])C([H])([H])[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1([H])C([H])([H])[C@]2([H])O[H]

InChI Identifier

InChI=1S/C20H30O5/c1-9-15-10(21)7-12-19(4)6-5-13(22)18(2,3)11(19)8-14(23)20(12,16(9)24)17(15)25/h10-15,17,21-23,25H,1,5-8H2,2-4H3/t10-,11+,12-,13-,14+,15+,17+,19+,20-/m0/s1

InChI Key

BRNLPJIEDLXFLS-WEMBNSTNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Isodon pharicus	JEOL database	Zhao, Y., et al, J. Nat. Prod. 72, 988 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
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	0.93	ALOGPS
logP	0.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.43 m³·mol⁻¹	ChemAxon
Polarizability	37.76 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

24628859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44179017

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao, Y., et al. (2009). Zhao, Y., et al, J. Nat. Prod. 72, 988 (2009). J. Nat. Prod..

Showing NP-Card for 3-epipseurata B (NP0034429)

MOL for NP0034429 (3-epipseurata B)

3D MOL for NP0034429 (3-epipseurata B)

3D SDF for NP0034429 (3-epipseurata B)

3D-SDF for NP0034429 (3-epipseurata B)

PDB for NP0034429 (3-epipseurata B)

3D PDB for NP0034429 (3-epipseurata B)

SMILES for NP0034429 (3-epipseurata B)

INCHI for NP0034429 (3-epipseurata B)

Structure for NP0034429 (3-epipseurata B)

3D Structure for NP0034429 (3-epipseurata B)