NP-MRD: Showing NP-Card for (3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one (NP0006850)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 03:46:14 UTC

Updated at

2021-07-15 16:55:58 UTC

NP-MRD ID

NP0006850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one

Provided By

NPAtlas

Description

(1R,2S,8aR)-1,8a-dimethyl-6-oxo-7-(propan-2-ylidene)-1,2,6,7,8,8a-hexahydronaphthalen-2-yl acetate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. (3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one is found in Penicillium and Penicillium roqueforti. (3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one was first documented in 2007 (PMID: 17253863). Based on a literature review very few articles have been published on (1R,2S,8aR)-1,8a-dimethyl-6-oxo-7-(propan-2-ylidene)-1,2,6,7,8,8a-hexahydronaphthalen-2-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118353D          

 42 43  0  0  0  0            999 V2000
    4.3390   -0.6482   -2.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -1.0887   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -2.1095   -0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545   -0.3768   -0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.7828    0.6538 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5852    0.2661    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    1.0248    2.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242    0.8911    1.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625    1.5094    2.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.4110    1.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090    1.9931    2.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    0.5725    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414    0.6965   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.6994    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.1429   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.4473    0.1532 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0406    0.0399    0.3444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4770    0.8561   -0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -1.1694    0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7020   -2.2451   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772    0.0157   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148   -1.5002   -3.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -0.0028   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -1.7150    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885    0.4346    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    1.8066    2.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    2.1325    3.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608    2.7177    0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0232    1.4425    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2588    1.7420   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.2579   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.0537   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177   -1.2151   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -0.6486   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -1.4006    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427    1.6247   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.4358   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640    0.2676   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341   -1.5832    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -2.8587   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -2.9622   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.8866   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  3  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19  5  1  0  0  0  0
 17  8  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 24  1  1  0  0  0
  6 25  1  0  0  0  0
  7 26  1  0  0  0  0
  9 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  1  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
M  END

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    4.3390   -0.6482   -2.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -1.0887   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -2.1095   -0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545   -0.3768   -0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.7828    0.6538 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5852    0.2661    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    1.0248    2.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242    0.8911    1.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625    1.5094    2.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.4110    1.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090    1.9931    2.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    0.5725    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414    0.6965   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.6994    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.1429   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.4473    0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406    0.0399    0.3444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4770    0.8561   -0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -1.1694    0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7020   -2.2451   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772    0.0157   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148   -1.5002   -3.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -0.0028   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -1.7150    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885    0.4346    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    1.8066    2.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    2.1325    3.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608    2.7177    0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0232    1.4425    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2588    1.7420   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.2579   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.0537   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177   -1.2151   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -0.6486   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -1.4006    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427    1.6247   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.4358   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640    0.2676   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341   -1.5832    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -2.8587   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -2.9622   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.8866   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19  5  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  1
  6 25  1  0
  7 26  1  0
  9 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  1
 20 40  1  0
 20 41  1  0
 20 42  1  0
M  END


  Mrv1652306242118353D          

 42 43  0  0  0  0            999 V2000
    4.3390   -0.6482   -2.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -1.0887   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -2.1095   -0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545   -0.3768   -0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.7828    0.6538 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5852    0.2661    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    1.0248    2.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242    0.8911    1.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625    1.5094    2.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.4110    1.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090    1.9931    2.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    0.5725    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414    0.6965   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.6994    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.1429   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.4473    0.1532 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0406    0.0399    0.3444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4770    0.8561   -0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -1.1694    0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7020   -2.2451   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772    0.0157   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148   -1.5002   -3.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -0.0028   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -1.7150    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885    0.4346    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    1.8066    2.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    2.1325    3.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608    2.7177    0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0232    1.4425    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2588    1.7420   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.2579   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.0537   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177   -1.2151   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -0.6486   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -1.4006    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427    1.6247   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.4358   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640    0.2676   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341   -1.5832    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -2.8587   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -2.9622   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.8866   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  3  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19  5  1  0  0  0  0
 17  8  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 24  1  1  0  0  0
  6 25  1  0  0  0  0
  7 26  1  0  0  0  0
  9 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  1  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(C([H])([H])[H])[C@@]2(C1=C([H])C(=O)C(=C(C([H])([H])[H])C([H])([H])[H])C2([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O3/c1-10(2)14-9-17(5)11(3)16(20-12(4)18)7-6-13(17)8-15(14)19/h6-8,11,16H,9H2,1-5H3/t11-,16-,17+/m0/s1

> <INCHI_KEY>
FJZBAGIMAUDSAO-MZPVMMEZSA-N

> <FORMULA>
C17H22O3

> <MOLECULAR_WEIGHT>
274.36

> <EXACT_MASS>
274.156894568

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.934716638748387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,8aR)-1,8a-dimethyl-6-oxo-7-(propan-2-ylidene)-1,2,6,7,8,8a-hexahydronaphthalen-2-yl acetate

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.0365260983333333

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.399777288640735

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
80.6348

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,8aR)-1,8a-dimethyl-6-oxo-7-(propan-2-ylidene)-2,8-dihydro-1H-naphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    4.3390   -0.6482   -2.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -1.0887   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -2.1095   -0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545   -0.3768   -0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.7828    0.6538 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5852    0.2661    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    1.0248    2.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242    0.8911    1.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625    1.5094    2.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.4110    1.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090    1.9931    2.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    0.5725    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414    0.6965   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.6994    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.1429   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.4473    0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406    0.0399    0.3444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4770    0.8561   -0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -1.1694    0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7020   -2.2451   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772    0.0157   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148   -1.5002   -3.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -0.0028   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -1.7150    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885    0.4346    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    1.8066    2.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    2.1325    3.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608    2.7177    0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0232    1.4425    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2588    1.7420   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.2579   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.0537   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177   -1.2151   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -0.6486   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -1.4006    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427    1.6247   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.4358   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640    0.2676   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341   -1.5832    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -2.8587   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -2.9622   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.8866   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19  5  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  1
  6 25  1  0
  7 26  1  0
  9 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  1
 20 40  1  0
 20 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.339  -0.648  -2.642  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.846  -1.089  -1.297  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.303  -2.110  -0.724  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.854  -0.377  -0.629  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.373  -0.783   0.654  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.585   0.266   1.664  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.595   1.025   2.075  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.224   0.891   1.570  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.763   1.509   2.186  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.154   1.411   1.732  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.109   1.993   2.302  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.362   0.573   0.548  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.441   0.697  -0.194  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.475   1.699   0.162  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.675  -0.143  -1.397  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.349  -0.447   0.153  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.041   0.040   0.344  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.477   0.856  -0.830  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.938  -1.169   0.583  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.702  -2.245  -0.444  0.00  0.00           C+0
HETATM   21  H   UNK     0       3.577   0.016  -3.110  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.615  -1.500  -3.280  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.237  -0.003  -2.447  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.931  -1.715   0.954  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.588   0.435   2.099  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.779   1.807   2.834  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.600   2.132   3.071  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.061   2.718   0.309  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.023   1.442   1.098  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.259   1.742  -0.647  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.978   0.258  -2.190  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.717  -0.054  -1.712  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.418  -1.215  -1.194  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.481  -0.649  -0.929  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.570  -1.401   0.682  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.243   1.625  -0.562  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.400   1.436  -1.214  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.864   0.268  -1.677  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.634  -1.583   1.569  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.194  -2.859  -0.196  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.569  -2.962  -0.347  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.714  -1.887  -1.478  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19   24                                             
CONECT    6    5    7   25                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   28   29   30                                             
CONECT   15   13   31   32   33                                             
CONECT   16   12   17   34   35                                             
CONECT   17   16   18   19    8                                             
CONECT   18   17   36   37   38                                             
CONECT   19   17   20    5   39                                             
CONECT   20   19   40   41   42                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27    9                                                            
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30   14                                                            
CONECT   31   15                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   18                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

RDKit          3D

42 43  0  0  0  0  0  0  0  0999 V2000
    4.3390   -0.6482   -2.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -1.0887   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035   -2.1095   -0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545   -0.3768   -0.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.7828    0.6538 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5852    0.2661    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    1.0248    2.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242    0.8911    1.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625    1.5094    2.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538    1.4110    1.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090    1.9931    2.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    0.5725    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414    0.6965   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.6994    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.1429   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.4473    0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406    0.0399    0.3444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4770    0.8561   -0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -1.1694    0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7020   -2.2451   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772    0.0157   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148   -1.5002   -3.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2366   -0.0028   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -1.7150    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885    0.4346    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    1.8066    2.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    2.1325    3.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0608    2.7177    0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0232    1.4425    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2588    1.7420   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.2579   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7168   -0.0537   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177   -1.2151   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -0.6486   -0.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -1.4006    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427    1.6247   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.4358   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640    0.2676   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6341   -1.5832    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943   -2.8587   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -2.9622   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -1.8866   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19  5  1  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  1
  6 25  1  0
  7 26  1  0
  9 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  1
 20 40  1  0
 20 41  1  0
 20 42  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1R,2S,8AR)-1,8a-dimethyl-6-oxo-7-(propan-2-ylidene)-1,2,6,7,8,8a-hexahydronaphthalen-2-yl acetic acid	Generator
(3S)-3-Acetoxyeremophil-1(2),7(11),9(10)-trien-8-one	MeSH
3-AET CPD	MeSH

Chemical Formula

C₁₇H₂₂O₃

Average Mass

274.3600 Da

Monoisotopic Mass

274.15689 Da

IUPAC Name

(1R,2S,8aR)-1,8a-dimethyl-6-oxo-7-(propan-2-ylidene)-1,2,6,7,8,8a-hexahydronaphthalen-2-yl acetate

Traditional Name

(1R,2S,8aR)-1,8a-dimethyl-6-oxo-7-(propan-2-ylidene)-2,8-dihydro-1H-naphthalen-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H](OC(C)=O)C=CC2=CC(=O)C(C[C@]12C)=C(C)C

InChI Identifier

InChI=1S/C17H22O3/c1-10(2)14-9-17(5)11(3)16(20-12(4)18)7-6-13(17)8-15(14)19/h6-8,11,16H,9H2,1-5H3/t11-,16-,17+/m0/s1

InChI Key

FJZBAGIMAUDSAO-MZPVMMEZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Penicillium	NPAtlas	17253863
Penicillium roqueforti	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Quinomethane
O-quinomethane
Cyclohexenone
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.57	ALOGPS
logP	3.04	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4.4	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	2	ChemAxon
Refractivity	80.63 m³·mol⁻¹	ChemAxon
Polarizability	30.93 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

NPAtlas ID

NPA007034

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17262762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16104919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sorensen D, Raditsis A, Trimble LA, Blackwell BA, Sumarah MW, Miller JD: Isolation and structure elucidation by LC-MS-SPE/NMR: PR toxin- and cuspidatol-related eremophilane sesquiterpenes from Penicillium roqueforti. J Nat Prod. 2007 Jan;70(1):121-3. doi: 10.1021/np060454v. [PubMed:17253863 ]

Showing NP-Card for (3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one (NP0006850)

MOL for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

3D MOL for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

3D SDF for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

3D-SDF for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

PDB for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

3D PDB for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

SMILES for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

INCHI for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

Structure for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)

3D Structure for NP0006850 ((3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one)