NP-MRD: Showing NP-Card for (1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione (NP0164882)

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Record Information

Version

2.0

Created at

2022-09-02 23:50:58 UTC

Updated at

2022-09-02 23:50:58 UTC

NP-MRD ID

NP0164882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione

Description

Transtaganolide D belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. (1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione is found in Thapsia transtagana. (1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione was first documented in 2009 (PMID: 19117487). Based on a literature review a small amount of articles have been published on transtaganolide D (PMID: 23681694) (PMID: 21442697).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201512D          

 25 28  0  0  1  0            999 V2000
    4.0574   -1.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.2456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9003   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657   -0.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008   -0.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820    0.5723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9317    0.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1137    0.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425   -0.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578    1.4632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8867    1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140    2.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    2.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2453    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    2.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6573    2.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4988    1.1235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2078   -0.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0615    0.6214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3836    1.2511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8960    2.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    2.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    2.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  1  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    3.0316   -1.2558    2.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387   -0.8938    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437   -1.0802   -0.0788 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8177   -1.4583   -1.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -2.3011    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564   -2.1183    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8210   -1.2035   -0.0893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2789   -1.1810    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0567   -1.3080   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6743   -2.3029    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.1645    0.8665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2746    1.1535   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9703    1.2289   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995    2.4003   -1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909    3.0236   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321    4.1045   -2.1441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824    5.4033   -1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7144    2.6919   -0.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9226    1.4171    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789    1.4530    0.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2572    0.1372   -0.3496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1402    0.1574    0.1328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2771    0.3617    1.5522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    0.3999    1.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9545    0.6171    3.1349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8442   -1.1043    2.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493   -1.7200    2.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0977   -0.4364    0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736   -2.5329   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6885   -0.7936   -1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859   -1.3031   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8824   -2.9324    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1526   -3.0015   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985   -1.6365    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462   -3.1118    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5801   -1.4944   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6570   -0.5846   -1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1242   -1.1213   -0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9377   -2.3230   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704   -3.2530    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7214   -2.1622    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571   -2.2637    2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6560    0.2455    1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0110    1.7191   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3767    2.7656   -1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265    5.5232   -1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3475    5.4880   -0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442    6.2013   -2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    0.2211   -1.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 24  1  0
 24 25  2  0
 24 23  1  0
 22 23  1  1
 22  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  1
  2  1  2  3
  3 21  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 18 15  1  0
 22 13  1  0
 21 22  1  0
  8 11  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 14 45  1  0
 12 44  1  0
 11 43  1  1
  7 36  1  6
  6 34  1  0
  6 35  1  0
  5 32  1  0
  5 33  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  2 28  1  0
  1 26  1  0
  1 27  1  0
 21 49  1  6
  9 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
M  END


  Mrv1652309032201512D          

 25 28  0  0  1  0            999 V2000
    4.0574   -1.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936   -0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -0.2456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9003   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657   -0.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008   -0.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820    0.5723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9317    0.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1137    0.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425   -0.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578    1.4632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8867    1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7140    2.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    2.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2453    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    2.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6573    2.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4988    1.1235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2078   -0.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0615    0.6214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3836    1.2511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8960    2.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    2.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    2.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  1  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0164882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C[C@@H]3C(=O)O[C@@]22[C@@H](CC[C@](C)(C=C)[C@@H]2C(=O)O1)C3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-6-19(4)8-7-13-18(2,3)12-9-11-10-14(23-5)24-17(22)15(19)20(11,13)25-16(12)21/h6,9-10,12-13,15H,1,7-8H2,2-5H3/t12-,13+,15+,19+,20-/m1/s1

> <INCHI_KEY>
WEROHVUUBZUWOZ-RTPXSMORSA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.407

> <EXACT_MASS>
344.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.148251704846665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,6R,7S,13R)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0^{3,13}.0^{7,13}]hexadeca-10,12(16)-diene-8,15-dione

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
3.122785087333333

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.0349540797608086

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
101.63909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,6R,7S,13R)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0^{3,13}.0^{7,13}]hexadeca-10,12(16)-diene-8,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       7.574  -3.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.388  -1.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.663  -0.459   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.147  -0.047   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.469  -1.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.228  -0.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.193   1.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.606   1.205   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.079   1.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.439  -0.326   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.841   2.731   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.389   3.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.933   3.738   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.416   4.393   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.791   3.610   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.991   4.576   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.427   4.020   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.264   2.097   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.200   0.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.721  -0.519   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.582   1.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.316   2.335   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.406   4.028   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.789   4.286   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.770   5.441   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   21                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21   13    7   23                                             
CONECT   23   22   24                                                       
CONECT   24   23   11   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₅

Average Mass

344.4070 Da

Monoisotopic Mass

344.16237 Da

IUPAC Name

(1S,3S,6R,7S,13R)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0^{3,13}.0^{7,13}]hexadeca-10,12(16)-diene-8,15-dione

Traditional Name

(1S,3S,6R,7S,13R)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0^{3,13}.0^{7,13}]hexadeca-10,12(16)-diene-8,15-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C[C@@H]3C(=O)O[C@@]22[C@@H](CC[C@](C)(C=C)[C@@H]2C(=O)O1)C3(C)C

InChI Identifier

InChI=1S/C20H24O5/c1-6-19(4)8-7-13-18(2,3)12-9-11-10-14(23-5)24-17(22)15(19)20(11,13)25-16(12)21/h6,9-10,12-13,15H,1,7-8H2,2-5H3/t12-,13+,15+,19+,20-/m1/s1

InChI Key

WEROHVUUBZUWOZ-RTPXSMORSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Thapsia transtagana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Delta valerolactone
Dihydropyranone
Delta_valerolactone
Oxane
Dicarboxylic acid or derivatives
Lactone
Ketene acetal or derivatives
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.01	ALOGPS
logP	3.12	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.64 m³·mol⁻¹	ChemAxon
Polarizability	36.15 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68112493

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nelson HM, Gordon JR, Virgil SC, Stoltz BM: Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications. Angew Chem Int Ed Engl. 2013 Jun 24;52(26):6699-703. doi: 10.1002/anie.201301212. Epub 2013 May 16. [PubMed:23681694 ]
Nelson HM, Murakami K, Virgil SC, Stoltz BM: A general approach to the basiliolide/transtaganolide natural products: total syntheses of basiliolide B, epi-8-basiliolide B, transtaganolide C, and transtaganolide D. Angew Chem Int Ed Engl. 2011 Apr 11;50(16):3688-91. doi: 10.1002/anie.201008003. Epub 2011 Mar 25. [PubMed:21442697 ]
Oguri H, Yamagishi Y, Hiruma T, Oikawa H: Skeletal and stereochemical diversification of tricyclic frameworks inspired by Ca(2+)-ATPase inhibitors, artemisinin and transtaganolide D. Org Lett. 2009 Feb 5;11(3):601-4. doi: 10.1021/ol802621u. [PubMed:19117487 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione (NP0164882)

MOL for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

3D MOL for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

3D SDF for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

3D-SDF for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

PDB for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

3D PDB for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

SMILES for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

INCHI for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

Structure for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)

3D Structure for NP0164882 ((1s,3s,6r,7s,13r)-6-ethenyl-10-methoxy-2,2,6-trimethyl-9,14-dioxatetracyclo[10.3.1.0³,¹³.0⁷,¹³]hexadeca-10,12(16)-diene-8,15-dione)