NP-MRD: Showing NP-Card for (+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide (NP0034050)

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Record Information

Version

1.0

Created at

2021-06-20 17:53:33 UTC

Updated at

2021-06-30 00:04:11 UTC

NP-MRD ID

NP0034050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide

Provided By

JEOL Database JEOL Logo

Description

CHEMBL506745 belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide is found in Eupatorium adenophorum. It was first documented in 2008 (He, L., et al.). Based on a literature review very few articles have been published on CHEMBL506745.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119533D          

 36 38  0  0  0  0            999 V2000
   -1.8522    2.8998   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.5495    0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    1.3498    1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -0.0035    2.5521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5809    0.0370    3.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.0289    5.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742   -0.1024    5.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -0.0651    5.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791   -0.1178    6.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.0509    4.7317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    0.0695    3.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2718   -1.0912    2.5456 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4475   -1.0886    1.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8865   -2.2715    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869   -1.1118    1.5529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9552   -1.0072    0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8668    0.3663   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.5190   -1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    3.7041    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    3.0428   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    3.0105   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    2.2162    2.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2568    2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    0.7339    6.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.0606    5.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -1.0360    6.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.0263    3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -1.0221    2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -2.0451    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -0.1696    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9757   -2.2832    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -2.2118   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -3.2252    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3049   -2.0834    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -1.7580   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -1.1865    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
 15 16  1  0  0  0  0
 15  4  1  0  0  0  0
 17  2  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  8 10  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  2  0  0  0  0
  2  3  2  0  0  0  0
  2  1  1  0  0  0  0
 15 13  1  0  0  0  0
  8  9  2  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 15 34  1  1  0  0  0
 13 14  1  0  0  0  0
 12 13  1  0  0  0  0
  4 23  1  1  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
  3 22  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 12 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  6  0  0  0
 11 27  1  6  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 14 33  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.8522    2.8998   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.5495    0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    1.3498    1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -0.0035    2.5521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5809    0.0370    3.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.0289    5.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742   -0.1024    5.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -0.0651    5.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791   -0.1178    6.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.0509    4.7317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    0.0695    3.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2718   -1.0912    2.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -1.0886    1.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8865   -2.2715    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869   -1.1118    1.5529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9552   -1.0072    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    0.3663   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.5190   -1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    3.7041    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    3.0428   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    3.0105   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    2.2162    2.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2568    2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    0.7339    6.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.0606    5.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -1.0360    6.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.0263    3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -1.0221    2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -2.0451    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -0.1696    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9757   -2.2832    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -2.2118   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -3.2252    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3049   -2.0834    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -1.7580   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -1.1865    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 15 16  1  0
 15  4  1  0
 17  2  1  0
  5  6  2  0
  6  8  1  0
  8 10  1  0
 17 16  1  0
 17 18  2  0
  2  3  2  0
  2  1  1  0
 15 13  1  0
  8  9  2  0
  4  5  1  0
  6  7  1  0
 11 12  1  0
 15 34  1  1
 13 14  1  0
 12 13  1  0
  4 23  1  1
 11  5  1  0
 11 10  1  0
  3 22  1  0
 16 35  1  0
 16 36  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  6
 11 27  1  6
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END


  Mrv1652306202119533D          

 36 38  0  0  0  0            999 V2000
   -1.8522    2.8998   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.5495    0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    1.3498    1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -0.0035    2.5521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5809    0.0370    3.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.0289    5.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742   -0.1024    5.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -0.0651    5.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791   -0.1178    6.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.0509    4.7317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    0.0695    3.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2718   -1.0912    2.5456 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4475   -1.0886    1.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8865   -2.2715    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869   -1.1118    1.5529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9552   -1.0072    0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8668    0.3663   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.5190   -1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    3.7041    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    3.0428   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    3.0105   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    2.2162    2.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2568    2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    0.7339    6.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.0606    5.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -1.0360    6.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.0263    3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -1.0221    2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -2.0451    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -0.1696    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9757   -2.2832    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -2.2118   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -3.2252    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3049   -2.0834    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -1.7580   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -1.1865    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
 15 16  1  0  0  0  0
 15  4  1  0  0  0  0
 17  2  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  8 10  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  2  0  0  0  0
  2  3  2  0  0  0  0
  2  1  1  0  0  0  0
 15 13  1  0  0  0  0
  8  9  2  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 15 34  1  1  0  0  0
 13 14  1  0  0  0  0
 12 13  1  0  0  0  0
  4 23  1  1  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
  3 22  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 12 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  6  0  0  0
 11 27  1  6  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 14 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C(=O)C([H])([H])[C@]2([H])[C@@]1([H])C1=C(C(=O)O[C@@]1([H])C([H])([H])[C@@]2([H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-7-5-13-14(9(3)15(17)18-13)11-4-8(2)12(16)6-10(7)11/h4,7,10-11,13H,5-6H2,1-3H3/t7-,10+,11+,13+/m1/s1

> <INCHI_KEY>
JCTYUEGJVULBEI-ROBVANNZSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.804458025457777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5R,5aS,9aR)-1,5,8-trimethyl-2H,3aH,4H,5H,5aH,6H,7H,9aH-naphtho[2,1-b]furan-2,7-dione

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.596092501666667

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.285827055763445

> <JCHEM_PKA_STRONGEST_BASIC>
-4.939877613052164

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
68.7655

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5R,5aS,9aR)-1,5,8-trimethyl-3aH,4H,5H,5aH,6H,9aH-naphtho[2,1-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.8522    2.8998   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.5495    0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    1.3498    1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -0.0035    2.5521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5809    0.0370    3.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.0289    5.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742   -0.1024    5.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -0.0651    5.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791   -0.1178    6.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.0509    4.7317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    0.0695    3.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2718   -1.0912    2.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -1.0886    1.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8865   -2.2715    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869   -1.1118    1.5529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9552   -1.0072    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    0.3663   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.5190   -1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    3.7041    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    3.0428   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    3.0105   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    2.2162    2.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2568    2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    0.7339    6.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.0606    5.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -1.0360    6.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.0263    3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -1.0221    2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -2.0451    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -0.1696    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9757   -2.2832    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -2.2118   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -3.2252    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3049   -2.0834    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -1.7580   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -1.1865    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 15 16  1  0
 15  4  1  0
 17  2  1  0
  5  6  2  0
  6  8  1  0
  8 10  1  0
 17 16  1  0
 17 18  2  0
  2  3  2  0
  2  1  1  0
 15 13  1  0
  8  9  2  0
  4  5  1  0
  6  7  1  0
 11 12  1  0
 15 34  1  1
 13 14  1  0
 12 13  1  0
  4 23  1  1
 11  5  1  0
 11 10  1  0
  3 22  1  0
 16 35  1  0
 16 36  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  6
 11 27  1  6
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 14 31  1  0
 14 32  1  0
 14 33  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      -1.852   2.900  -0.067  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.767   1.550   0.571  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.639   1.350   1.894  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.525  -0.004   2.552  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.581   0.037   3.711  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.820  -0.029   5.022  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.074  -0.102   5.803  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.496  -0.065   5.680  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.679  -0.118   6.882  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.474  -0.051   4.732  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.874   0.070   3.446  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.272  -1.091   2.546  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.448  -1.089   1.243  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.887  -2.272   0.373  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.087  -1.112   1.553  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.955  -1.007   0.292  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.867   0.366  -0.338  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.935   0.519  -1.556  0.00  0.00           O+0
HETATM   19  H   UNK     0      -1.798   3.704   0.674  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.027   3.043  -0.773  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.798   3.010  -0.608  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.632   2.216   2.555  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.530  -0.257   2.916  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.136   0.734   6.506  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.959  -0.061   5.162  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.117  -1.036   6.373  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.180   1.026   3.007  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.344  -1.022   2.323  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.143  -2.045   3.076  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.694  -0.170   0.695  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.976  -2.283   0.256  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.459  -2.212  -0.631  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.586  -3.225   0.820  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.305  -2.083   2.021  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.671  -1.758  -0.450  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.008  -1.187   0.541  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2   17    3    1                                                  
CONECT    3    4    2   22                                                  
CONECT    4    3   15    5   23                                             
CONECT    5    6    4   11                                                  
CONECT    6    5    8    7                                                  
CONECT    7    6   24   25   26                                             
CONECT    8    6   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   12    5   10   27                                             
CONECT   12   11   13   28   29                                             
CONECT   13   15   14   12   30                                             
CONECT   14   13   31   32   33                                             
CONECT   15   16    4   13   34                                             
CONECT   16   15   17   35   36                                             
CONECT   17    2   16   18                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    7                                                            
CONECT   25    7                                                            
CONECT   26    7                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   14                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -1.8522    2.8998   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.5495    0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    1.3498    1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5254   -0.0035    2.5521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5809    0.0370    3.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -0.0289    5.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742   -0.1024    5.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -0.0651    5.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6791   -0.1178    6.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.0509    4.7317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8744    0.0695    3.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2718   -1.0912    2.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -1.0886    1.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8865   -2.2715    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869   -1.1118    1.5529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9552   -1.0072    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    0.3663   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.5190   -1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    3.7041    0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    3.0428   -0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    3.0105   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    2.2162    2.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -0.2568    2.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    0.7339    6.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.0606    5.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172   -1.0360    6.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.0263    3.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3441   -1.0221    2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -2.0451    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -0.1696    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9757   -2.2832    0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -2.2118   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -3.2252    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3049   -2.0834    2.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -1.7580   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -1.1865    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 15 16  1  0
 15  4  1  0
 17  2  1  0
  5  6  2  0
  6  8  1  0
  8 10  1  0
 17 16  1  0
 17 18  2  0
  2  3  2  0
  2  1  1  0
 15 13  1  0
  8  9  2  0
  4  5  1  0
  6  7  1  0
 11 12  1  0
 15 34  1  1
 13 14  1  0
 12 13  1  0
  4 23  1  1
 11  5  1  0
 11 10  1  0
  3 22  1  0
 16 35  1  0
 16 36  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  6
 11 27  1  6
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3060 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(3aS,5R,5aS,9aR)-1,5,8-trimethyl-2H,3aH,4H,5H,5aH,6H,7H,9aH-naphtho[2,1-b]furan-2,7-dione

Traditional Name

(3aS,5R,5aS,9aR)-1,5,8-trimethyl-3aH,4H,5H,5aH,6H,9aH-naphtho[2,1-b]furan-2,7-dione

CAS Registry Number

Not Available

SMILES

[H]C1=C(C(=O)C([H])([H])[C@]2([H])[C@@]1([H])C1=C(C(=O)O[C@@]1([H])C([H])([H])[C@@]2([H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H18O3/c1-7-5-13-14(9(3)15(17)18-13)11-4-8(2)12(16)6-10(7)11/h4,7,10-11,13H,5-6H2,1-3H3/t7-,10+,11+,13+/m1/s1

InChI Key

JCTYUEGJVULBEI-ROBVANNZSA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ageratina adenophora	JEOL database	He, L., et al, J. Nat. Prod. 71, 1485 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Cadinane sesquiterpenoid
Sesquiterpenoid
Naphthofuran
Cyclohexenone
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.07	ALOGPS
logP	2.6	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.77 m³·mol⁻¹	ChemAxon
Polarizability	26.8 Å³	ChemAxon
Number of Rings	3	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

24713056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25016668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

He, L., et al. (2008). He, L., et al, J. Nat. Prod. 71, 1485 (2008). J. Nat. Prod..

Showing NP-Card for (+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide (NP0034050)

MOL for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

3D MOL for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

3D SDF for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

3D-SDF for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

PDB for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

3D PDB for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

SMILES for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

INCHI for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

Structure for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)

3D Structure for NP0034050 ((+)-(5R,7S,9R,10S)-2-oxocadinan-3,6(11)-dien-12,7-olide)