NP-MRD: Showing NP-Card for (+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide (NP0036339)

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Record Information

Version

1.0

Created at

2021-06-20 19:32:17 UTC

Updated at

2021-06-30 00:07:56 UTC

NP-MRD ID

NP0036339

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide

Provided By

JEOL Database JEOL Logo

Description

Rel-(+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide is found in Croton gratissimus. It was first documented in 2011 (PMID: 22032651). Based on a literature review very few articles have been published on rel-(+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121323D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202121323D          

 55 56  0  0  0  0            999 V2000
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    0.4150    0.2507    0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5066   -0.5836    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016   -1.8190    2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4644   -3.5013    2.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7876   -2.3772    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.9641   -0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -3.2877    0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505   -4.1558   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6503   -3.0491   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -1.8871   -0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0516   -2.0862   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2842   -3.2721   -3.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9182   -1.7330   -4.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6247    0.1915   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767   -2.6962   -4.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762   -1.5894   -5.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247   -0.9677   -5.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3194   -1.2940   -3.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8484    2.0539   -3.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9094    0.6718   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    2.7061   -0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252    3.2156   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 13  2  0  0  0  0
 21 22  1  0  0  0  0
 13 14  1  0  0  0  0
  2  3  1  0  0  0  0
 14 17  1  0  0  0  0
  4  6  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7  8  1  0  0  0  0
 20 23  1  0  0  0  0
  6  7  2  0  0  0  0
 18 25  1  0  0  0  0
 25 23  1  0  0  0  0
  8 11  1  0  0  0  0
 23 24  2  0  0  0  0
  8 10  1  6  0  0  0
 21 20  1  0  0  0  0
  8  9  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  6  0  0  0
 20 19  2  0  0  0  0
 14 15  1  0  0  0  0
 22  4  1  0  0  0  0
 14 16  1  1  0  0  0
  7 35  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 22 54  1  0  0  0  0
 22 55  1  0  0  0  0
  6 34  1  0  0  0  0
  2 29  1  1  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 19 51  1  0  0  0  0
 12 42  1  0  0  0  0
 13 43  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 18 50  1  6  0  0  0
 10 39  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
  5 33  1  0  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 15 46  1  0  0  0  0
 16 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036339

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(\C([H])=C([H])\[C@](O[H])(C([H])([H])C([H])([H])C2=C([H])[C@]([H])(OC2=O)C([H])([H])[C@](O[H])(\C([H])=C([H])\C1([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-14(2)20(24)9-6-15-12-16(25-17(15)21)13-19(4,23)8-5-7-18(3,22)10-11-20/h5,8,10-12,14,16,22-24H,6-7,9,13H2,1-4H3/b8-5+,11-10+/t16-,18+,19+,20+/m0/s1

> <INCHI_KEY>
PZFBVODTZGEVTO-MCERNNHQSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.702355513605866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5E,7R,9E,11S,13R)-4,7,11-trihydroxy-7,11-dimethyl-4-(propan-2-yl)-14-oxabicyclo[11.2.1]hexadeca-1(16),5,9-trien-15-one

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.204241620999999

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.997866535327805

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.574217979294232

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9664364706125133

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
99.1994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5E,7R,9E,11S,13R)-4,7,11-trihydroxy-4-isopropyl-7,11-dimethyl-14-oxabicyclo[11.2.1]hexadeca-1(16),5,9-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
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   -1.3724    2.6596    0.8858 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3602    2.1145    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9255   -3.1676   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3360   -2.7831   -1.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4714   -2.1052   -1.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -1.5298   -3.0880 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3907   -2.2023   -3.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3032   -0.1549   -2.8271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818   -1.6775   -4.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667   -0.6707   -4.6900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9693   -0.4965   -3.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166    0.7879   -3.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    1.4367   -2.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    2.3375   -1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    1.5245   -4.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    2.7238   -4.0246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777    0.6526   -4.8745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7907    4.0687   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457    4.6972    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943    4.5822   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3960    2.7573    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773    2.8221    2.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3509    1.9427    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5066   -0.5836    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016   -1.8190    2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4644   -3.5013    2.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7876   -2.3772    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.9641   -0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -3.2877    0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505   -4.1558   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6503   -3.0491   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -1.8871   -0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0516   -2.0862   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2842   -3.2721   -3.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9182   -1.7330   -4.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6247    0.1915   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767   -2.6962   -4.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762   -1.5894   -5.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247   -0.9677   -5.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3194   -1.2940   -3.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8484    2.0539   -3.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9094    0.6718   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    2.7061   -0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252    3.2156   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  1  1  0
 12 13  2  0
 21 22  1  0
 13 14  1  0
  2  3  1  0
 14 17  1  0
  4  6  1  0
 17 18  1  0
 18 19  1  0
  7  8  1  0
 20 23  1  0
  6  7  2  0
 18 25  1  0
 25 23  1  0
  8 11  1  0
 23 24  2  0
  8 10  1  6
 21 20  1  0
  8  9  1  0
  4  2  1  0
  4  5  1  6
 20 19  2  0
 14 15  1  0
 22  4  1  0
 14 16  1  1
  7 35  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
  6 34  1  0
  2 29  1  1
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
 11 40  1  0
 11 41  1  0
 19 51  1  0
 12 42  1  0
 13 43  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  6
 10 39  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
  5 33  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  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      -1.829   4.078   0.508  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.372   2.660   0.886  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.360   2.115   1.931  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.202   1.712  -0.351  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.479   1.503  -0.975  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.668   0.353   0.075  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.427  -0.725   0.341  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.960  -2.153   0.529  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.831  -2.478   2.017  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.340  -2.307  -0.051  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.926  -3.168  -0.156  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.336  -2.783  -1.566  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.471  -2.105  -1.806  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.026  -1.530  -3.088  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.391  -2.202  -3.325  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.303  -0.155  -2.827  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.182  -1.678  -4.378  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.067  -0.671  -4.690  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.969  -0.497  -3.717  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.817   0.788  -3.396  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.228   1.437  -2.562  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.246   2.337  -1.405  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.867   1.525  -4.110  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.063   2.724  -4.025  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.578   0.653  -4.875  0.00  0.00           O+0
HETATM   26  H   UNK     0      -2.791   4.069  -0.015  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.946   4.697   1.404  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.094   4.582  -0.126  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.396   2.757   1.381  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.477   2.822   2.760  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.351   1.943   1.498  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.007   1.177   2.369  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.741   2.344  -1.396  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.415   0.251   0.121  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.507  -0.584   0.372  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.102  -1.819   2.503  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.464  -3.501   2.160  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.788  -2.377   2.542  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.273  -1.964  -0.957  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.828  -3.288   0.460  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.450  -4.156  -0.207  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.650  -3.049  -2.363  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.108  -1.887  -0.945  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.052  -2.086  -2.457  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.284  -3.272  -3.537  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.918  -1.733  -4.164  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.625   0.192  -2.212  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.777  -2.696  -4.436  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.876  -1.589  -5.226  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.625  -0.968  -5.650  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.319  -1.294  -3.392  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.848   2.054  -3.226  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.909   0.672  -2.169  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.655   2.706  -0.896  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.725   3.216  -1.855  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3    4   29                                             
CONECT    3    2   30   31   32                                             
CONECT    4    6    2    5   22                                             
CONECT    5    4   33                                                       
CONECT    6    4    7   34                                                  
CONECT    7    8    6   35                                                  
CONECT    8    7   11   10    9                                             
CONECT    9    8   36   37   38                                             
CONECT   10    8   39                                                       
CONECT   11   12    8   40   41                                             
CONECT   12   11   13   42                                                  
CONECT   13   12   14   43                                                  
CONECT   14   13   17   15   16                                             
CONECT   15   14   44   45   46                                             
CONECT   16   14   47                                                       
CONECT   17   14   18   48   49                                             
CONECT   18   17   19   25   50                                             
CONECT   19   18   20   51                                                  
CONECT   20   23   21   19                                                  
CONECT   21   22   20   52   53                                             
CONECT   22   21    4   54   55                                             
CONECT   23   20   25   24                                                  
CONECT   24   23                                                            
CONECT   25   18   23                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  112    0
END

RDKit          3D

55 56  0  0  0  0  0  0  0  0999 V2000
   -1.8291    4.0779    0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724    2.6596    0.8858 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3602    2.1145    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015    1.7119   -0.3508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4788    1.5032   -0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677    0.3534    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -0.7253    0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9600   -2.1527    0.5292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8311   -2.4782    2.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3400   -2.3072   -0.0509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9255   -3.1676   -0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3360   -2.7831   -1.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4714   -2.1052   -1.8062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -1.5298   -3.0880 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3907   -2.2023   -3.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3032   -0.1549   -2.8271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818   -1.6775   -4.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667   -0.6707   -4.6900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9693   -0.4965   -3.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166    0.7879   -3.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    1.4367   -2.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    2.3375   -1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    1.5245   -4.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    2.7238   -4.0246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777    0.6526   -4.8745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7907    4.0687   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457    4.6972    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943    4.5822   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3960    2.7573    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773    2.8221    2.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3509    1.9427    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0067    1.1767    2.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408    2.3443   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150    0.2507    0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5066   -0.5836    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016   -1.8190    2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4644   -3.5013    2.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7876   -2.3772    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.9641   -0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -3.2877    0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505   -4.1558   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6503   -3.0491   -2.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -1.8871   -0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0516   -2.0862   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2842   -3.2721   -3.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9182   -1.7330   -4.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6247    0.1915   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767   -2.6962   -4.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762   -1.5894   -5.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247   -0.9677   -5.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3194   -1.2940   -3.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8484    2.0539   -3.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9094    0.6718   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    2.7061   -0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252    3.2156   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  1  1  0
 12 13  2  0
 21 22  1  0
 13 14  1  0
  2  3  1  0
 14 17  1  0
  4  6  1  0
 17 18  1  0
 18 19  1  0
  7  8  1  0
 20 23  1  0
  6  7  2  0
 18 25  1  0
 25 23  1  0
  8 11  1  0
 23 24  2  0
  8 10  1  6
 21 20  1  0
  8  9  1  0
  4  2  1  0
  4  5  1  6
 20 19  2  0
 14 15  1  0
 22  4  1  0
 14 16  1  1
  7 35  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
  6 34  1  0
  2 29  1  1
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
 11 40  1  0
 11 41  1  0
 19 51  1  0
 12 42  1  0
 13 43  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  6
 10 39  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
  5 33  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(4S,5E,7R,9E,11S,13R)-4,7,11-trihydroxy-7,11-dimethyl-4-(propan-2-yl)-14-oxabicyclo[11.2.1]hexadeca-1(16),5,9-trien-15-one

Traditional Name

(4S,5E,7R,9E,11S,13R)-4,7,11-trihydroxy-4-isopropyl-7,11-dimethyl-14-oxabicyclo[11.2.1]hexadeca-1(16),5,9-trien-15-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(\C([H])=C([H])\[C@](O[H])(C([H])([H])C([H])([H])C2=C([H])[C@]([H])(OC2=O)C([H])([H])[C@](O[H])(\C([H])=C([H])\C1([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H30O5/c1-14(2)20(24)9-6-15-12-16(25-17(15)21)13-19(4,23)8-5-7-18(3,22)10-11-20/h5,8,10-12,14,16,22-24H,6-7,9,13H2,1-4H3/b8-5+,11-10+/t16-,18+,19+,20+/m0/s1

InChI Key

PZFBVODTZGEVTO-MCERNNHQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Croton gratissimus	JEOL database	Langat, M. K., et al, J. Nat. Prod. 74, 2349 (2011)

Chemical Taxonomy

Classification

Not classified

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	1.86	ALOGPS
logP	2.2	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.2 m³·mol⁻¹	ChemAxon
Polarizability	37.7 Å³	ChemAxon
Number of Rings	2	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

29368035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

68873

Good Scents ID

Not Available

References

General References

Langat MK, Crouch NR, Smith PJ, Mulholland DA: Cembranolides from the leaves of Croton gratissimus. J Nat Prod. 2011 Nov 28;74(11):2349-55. doi: 10.1021/np2002012. Epub 2011 Oct 27. [PubMed:22032651 ]
Langat, M. K., et al. (2011). Langat, M. K., et al, J. Nat. Prod. 74, 2349 (2011). J. Nat. Prod..

Showing NP-Card for (+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide (NP0036339)

MOL for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D MOL for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D SDF for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D-SDF for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

PDB for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D PDB for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

SMILES for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

INCHI for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

Structure for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D Structure for NP0036339 ((+)-(1S*,4R*,8S*,10R*)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

Showing NP-Card for (+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide (NP0036339)

MOL for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D MOL for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D SDF for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D-SDF for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

PDB for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D PDB for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

SMILES for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

INCHI for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

Structure for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)

3D Structure for NP0036339 ((+)-(1S,4R,8S,10R)-1,4,8-trihydroxycembra-2E,6E,11Z-trien-20,10-olide)