NP-MRD: Showing NP-Card for 6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide (NP0039004)

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Record Information

Version

2.0

Created at

2021-06-20 21:33:18 UTC

Updated at

2021-06-30 00:12:06 UTC

NP-MRD ID

NP0039004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide

Provided By

JEOL Database JEOL Logo

Description

3,4Abeta,5beta-Trimethyl-4beta,9aalpha-dihydroxy-4,4a,5,6,7,9a-hexahydronaphtho[2,3-b]furan-2,8-dione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide is found in Ligularia virgaurea and Ligularia virgaurea spp. oligocephala. 6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide was first documented in 2004 (Wu, Q.-X., et al.). Based on a literature review very few articles have been published on 3,4abeta,5beta-Trimethyl-4beta,9aalpha-dihydroxy-4,4a,5,6,7,9a-hexahydronaphtho[2,3-b]furan-2,8-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123333D          

 38 40  0  0  0  0            999 V2000
   -0.2865   -3.4300    3.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -3.1238    2.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -2.4549    1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -1.6894    0.5541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3789   -1.8990    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213   -0.1527    0.5427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1248    0.4981    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0132    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -0.9824    0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238   -2.3818    0.9474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4693   -3.1680   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0768   -2.9366    1.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139   -3.4713    2.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -4.1098    3.8881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885    1.3549    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    1.7466    0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.1418   -0.9561 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1380    2.0214   -0.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3300    0.5586   -0.6985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8630    0.5285   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -2.8780    3.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -4.4989    3.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166   -3.1671    4.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -2.0788   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -2.8335    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    1.5547    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415    0.0032    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077    0.4392    2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -0.7921    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918   -3.0489   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.1963   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844    1.7828   -1.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    2.6129    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    2.4765   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.0305   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2331    1.0552   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.4930   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059    1.0142    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 10  3  1  0  0  0  0
  8 15  1  0  0  0  0
 19 20  1  0  0  0  0
  8  6  1  0  0  0  0
 17 18  1  0  0  0  0
  3  2  2  0  0  0  0
  2 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 10  1  0  0  0  0
 17 15  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
 15 16  2  0  0  0  0
 19  6  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  2  0  0  0  0
  6  7  1  1  0  0  0
  6  4  1  0  0  0  0
 10 11  1  6  0  0  0
  4  3  1  0  0  0  0
 13 14  2  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 20 38  1  0  0  0  0
  4 24  1  6  0  0  0
  9 29  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  5 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
 11 30  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.2865   -3.4300    3.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -3.1238    2.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -2.4549    1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -1.6894    0.5541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3789   -1.8990    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213   -0.1527    0.5427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1248    0.4981    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0132    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -0.9824    0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238   -2.3818    0.9474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4693   -3.1680   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0768   -2.9366    1.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139   -3.4713    2.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -4.1098    3.8881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885    1.3549    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    1.7466    0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.1418   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    2.0214   -0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300    0.5586   -0.6985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8630    0.5285   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -2.8780    3.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -4.4989    3.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166   -3.1671    4.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -2.0788   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -2.8335    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    1.5547    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415    0.0032    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077    0.4392    2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -0.7921    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918   -3.0489   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.1963   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844    1.7828   -1.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    2.6129    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    2.4765   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.0305   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2331    1.0552   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.4930   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059    1.0142    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 10  3  1  0
  8 15  1  0
 19 20  1  0
  8  6  1  0
 17 18  1  0
  3  2  2  0
  2 13  1  0
 13 12  1  0
 12 10  1  0
 17 15  1  0
  2  1  1  0
 18 19  1  0
 15 16  2  0
 19  6  1  0
  4  5  1  0
  8  9  2  0
  6  7  1  1
  6  4  1  0
 10 11  1  6
  4  3  1  0
 13 14  2  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 20 37  1  0
 20 38  1  0
  4 24  1  6
  9 29  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 11 30  1  0
M  END


  Mrv1652306202123333D          

 38 40  0  0  0  0            999 V2000
   -0.2865   -3.4300    3.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -3.1238    2.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -2.4549    1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -1.6894    0.5541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3789   -1.8990    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213   -0.1527    0.5427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1248    0.4981    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0132    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -0.9824    0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238   -2.3818    0.9474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4693   -3.1680   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0768   -2.9366    1.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139   -3.4713    2.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -4.1098    3.8881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885    1.3549    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    1.7466    0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.1418   -0.9561 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1380    2.0214   -0.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3300    0.5586   -0.6985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8630    0.5285   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -2.8780    3.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -4.4989    3.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166   -3.1671    4.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -2.0788   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -2.8335    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    1.5547    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415    0.0032    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077    0.4392    2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -0.7921    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918   -3.0489   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.1963   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844    1.7828   -1.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    2.6129    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    2.4765   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.0305   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2331    1.0552   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.4930   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059    1.0142    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 10  3  1  0  0  0  0
  8 15  1  0  0  0  0
 19 20  1  0  0  0  0
  8  6  1  0  0  0  0
 17 18  1  0  0  0  0
  3  2  2  0  0  0  0
  2 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 10  1  0  0  0  0
 17 15  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
 15 16  2  0  0  0  0
 19  6  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  2  0  0  0  0
  6  7  1  1  0  0  0
  6  4  1  0  0  0  0
 10 11  1  6  0  0  0
  4  3  1  0  0  0  0
 13 14  2  0  0  0  0
 17 31  1  0  0  0  0
 17 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 20 38  1  0  0  0  0
  4 24  1  6  0  0  0
  9 29  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  5 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
 11 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C2=C(C(=O)O[C@]2(O[H])C([H])=C2C(=O)C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-7-4-5-10(16)9-6-15(19)11(8(2)13(18)20-15)12(17)14(7,9)3/h6-7,12,17,19H,4-5H2,1-3H3/t7-,12+,14+,15+/m0/s1

> <INCHI_KEY>
KSIHDKSKQWRYLV-YQKRUCBRSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.21209452736153

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.5004403366666672

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.922009629137701

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.755618683512022

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3121569478313333

> <JCHEM_POLAR_SURFACE_AREA>
83.82999999999998

> <JCHEM_REFRACTIVITY>
71.3668

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,9aR)-4,9a-dihydroxy-3,4a,5-trimethyl-4H,5H,6H,7H-naphtho[2,3-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.2865   -3.4300    3.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -3.1238    2.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -2.4549    1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -1.6894    0.5541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3789   -1.8990    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213   -0.1527    0.5427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1248    0.4981    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0132    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -0.9824    0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238   -2.3818    0.9474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4693   -3.1680   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0768   -2.9366    1.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139   -3.4713    2.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -4.1098    3.8881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885    1.3549    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    1.7466    0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.1418   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    2.0214   -0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300    0.5586   -0.6985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8630    0.5285   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -2.8780    3.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -4.4989    3.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166   -3.1671    4.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -2.0788   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -2.8335    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    1.5547    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415    0.0032    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077    0.4392    2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -0.7921    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918   -3.0489   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.1963   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844    1.7828   -1.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    2.6129    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    2.4765   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.0305   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2331    1.0552   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.4930   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059    1.0142    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 10  3  1  0
  8 15  1  0
 19 20  1  0
  8  6  1  0
 17 18  1  0
  3  2  2  0
  2 13  1  0
 13 12  1  0
 12 10  1  0
 17 15  1  0
  2  1  1  0
 18 19  1  0
 15 16  2  0
 19  6  1  0
  4  5  1  0
  8  9  2  0
  6  7  1  1
  6  4  1  0
 10 11  1  6
  4  3  1  0
 13 14  2  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 20 37  1  0
 20 38  1  0
  4 24  1  6
  9 29  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 11 30  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      -0.287  -3.430   3.472  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.828  -3.124   2.548  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.917  -2.455   1.396  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.053  -1.689   0.554  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.379  -1.899   1.020  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.321  -0.153   0.543  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.125   0.498   1.879  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.843   0.013   0.449  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.734  -0.982   0.635  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.324  -2.382   0.947  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.469  -3.168  -0.218  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.077  -2.937   2.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.214  -3.471   2.904  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.542  -4.110   3.888  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.389   1.355   0.097  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.451   1.747   0.572  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.649   2.142  -0.956  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.138   2.021  -0.834  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.330   0.559  -0.699  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.863   0.529  -0.737  0.00  0.00           C+0
HETATM   21  H   UNK     0      -1.198  -2.878   3.234  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.519  -4.499   3.443  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.017  -3.167   4.501  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.014  -2.079  -0.472  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.594  -2.833   0.852  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.156   1.555   1.941  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.342   0.003   2.739  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.208   0.439   2.024  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.802  -0.792   0.546  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.392  -3.049  -0.498  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.934   3.196  -0.870  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.984   1.783  -1.936  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.212   2.613   0.020  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.316   2.477  -1.724  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.012   0.031  -1.601  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.233   1.055  -1.624  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.245  -0.493  -0.803  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.306   1.014   0.138  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3   13    1                                                  
CONECT    3   10    2    4                                                  
CONECT    4    5    6    3   24                                             
CONECT    5    4   25                                                       
CONECT    6    8   19    7    4                                             
CONECT    7    6   26   27   28                                             
CONECT    8   15    6    9                                                  
CONECT    9   10    8   29                                                  
CONECT   10    9    3   12   11                                             
CONECT   11   10   30                                                       
CONECT   12   13   10                                                       
CONECT   13    2   12   14                                                  
CONECT   14   13                                                            
CONECT   15    8   17   16                                                  
CONECT   16   15                                                            
CONECT   17   18   15   31   32                                             
CONECT   18   17   19   33   34                                             
CONECT   19   20   18    6   35                                             
CONECT   20   19   36   37   38                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   11                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   20                                                            
CONECT   38   20                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
   -0.2865   -3.4300    3.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -3.1238    2.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174   -2.4549    1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -1.6894    0.5541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3789   -1.8990    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213   -0.1527    0.5427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1248    0.4981    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0132    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -0.9824    0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3238   -2.3818    0.9474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4693   -3.1680   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0768   -2.9366    1.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2139   -3.4713    2.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -4.1098    3.8881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885    1.3549    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    1.7466    0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    2.1418   -0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    2.0214   -0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300    0.5586   -0.6985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8630    0.5285   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -2.8780    3.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -4.4989    3.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166   -3.1671    4.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -2.0788   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -2.8335    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    1.5547    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415    0.0032    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077    0.4392    2.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -0.7921    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918   -3.0489   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    3.1963   -0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844    1.7828   -1.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    2.6129    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    2.4765   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.0305   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2331    1.0552   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.4930   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059    1.0142    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 10  3  1  0
  8 15  1  0
 19 20  1  0
  8  6  1  0
 17 18  1  0
  3  2  2  0
  2 13  1  0
 13 12  1  0
 12 10  1  0
 17 15  1  0
  2  1  1  0
 18 19  1  0
 15 16  2  0
 19  6  1  0
  4  5  1  0
  8  9  2  0
  6  7  1  1
  6  4  1  0
 10 11  1  6
  4  3  1  0
 13 14  2  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 20 37  1  0
 20 38  1  0
  4 24  1  6
  9 29  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 11 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
3,4Abeta,5b-trimethyl-4b,9aalpha-dihydroxy-4,4a,5,6,7,9a-hexahydronaphtho[2,3-b]furan-2,8-dione	Generator
3,4Abeta,5β-trimethyl-4β,9aalpha-dihydroxy-4,4a,5,6,7,9a-hexahydronaphtho[2,3-b]furan-2,8-dione	Generator

Chemical Formula

C₁₅H₁₈O₅

Average Mass

278.3040 Da

Monoisotopic Mass

278.11542 Da

IUPAC Name

(4S,4aR,5S,9aR)-4,9a-dihydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,9aH-naphtho[2,3-b]furan-2,8-dione

Traditional Name

(4S,4aR,5S,9aR)-4,9a-dihydroxy-3,4a,5-trimethyl-4H,5H,6H,7H-naphtho[2,3-b]furan-2,8-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C2=C(C(=O)O[C@]2(O[H])C([H])=C2C(=O)C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H18O5/c1-7-4-5-10(16)9-6-15(19)11(8(2)13(18)20-15)12(17)14(7,9)3/h6-7,12,17,19H,4-5H2,1-3H3/t7-,12+,14+,15+/m0/s1

InChI Key

KSIHDKSKQWRYLV-YQKRUCBRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Ligularia virgaurea	LOTUS Database	35616633
Ligularia virgaurea spp. oligocephala	JEOL database	Wu, Q.-X., et al, Org. Lett. 6, 2313 (2004)

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
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen 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	0.84	ALOGPS
logP	1.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.76	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.37 m³·mol⁻¹	ChemAxon
Polarizability	28.21 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

9336851

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11161751

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu, Q.-X., et al. (2004). Wu, Q.-X., et al, Org. Lett. 6, 2313 (2004). Org. Lett..

Showing NP-Card for 6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide (NP0039004)

MOL for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

3D MOL for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

3D SDF for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

3D-SDF for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

PDB for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

3D PDB for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

SMILES for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

INCHI for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

Structure for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)

3D Structure for NP0039004 (6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide)