NP-MRD: Showing NP-Card for volvalerenal E (NP0035509)

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Record Information

Version

2.0

Created at

2021-06-20 18:56:06 UTC

Updated at

2021-06-30 00:06:31 UTC

NP-MRD ID

NP0035509

Secondary Accession Numbers

None

Natural Product Identification

Common Name

volvalerenal E

Provided By

JEOL Database JEOL Logo

Description

[(1R,4E,8E,10R)-8-formyl-11,11-dimethylbicyclo[8.1.0]Undeca-4,8-dien-4-yl]methyl acetate belongs to the class of organic compounds known as bicyclogermacrane and isolepidozane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the bicyclogermacrane (3,7,11,11-tetramethylbicyclo[8.1.0]Undecane, 9CI) skeleton or the isolepidozane skeleton. volvalerenal E is found in Valeriana officinalis var. latifolia. volvalerenal E was first documented in 2010 (Wang, P. -C., et al.). [(1R,4E,8E,10R)-8-formyl-11,11-dimethylbicyclo[8.1.0]Undeca-4,8-dien-4-yl]methyl acetate is possibly neutral.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120563D          

 44 45  0  0  0  0            999 V2000
   -0.4787   -3.3822    3.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -3.0391    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -3.8589    0.9968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -1.6942    1.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2740    0.3418 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2120    0.2325    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    1.0136    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    2.5173   -0.0055 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6149    3.3051   -1.0599 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7458    2.8387   -2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    3.1119   -3.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673    3.6896   -2.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326    2.2491   -3.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    1.8719   -2.6863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321    0.4918   -2.0717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1879    0.3124   -0.6887 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2055    0.7478    0.4178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4498    0.8094   -3.3126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9429    1.0055   -3.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1208   -4.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -2.9025    3.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -4.4654    3.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -3.0639    3.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -1.5706    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -1.7617   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    0.5195   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    2.7546   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    2.9073    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    3.3487   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    4.3537   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    2.7644   -4.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.0049   -4.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    2.6878   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.1878   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -0.7454   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193    0.8727   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.8386    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    0.4115    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.6563   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    1.4661   -4.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    0.0408   -3.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -0.1583   -4.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351    0.7748   -5.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6245   -0.7987   -4.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 18  1  0  0  0  0
 13 14  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  6  1  0  0  0  0
 14 33  1  1  0  0  0
  8  7  1  0  0  0  0
 15 34  1  6  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
  9 10  1  0  0  0  0
 18 19  1  1  0  0  0
 11 12  2  0  0  0  0
 18 20  1  0  0  0  0
 10 13  2  0  0  0  0
  5  4  1  0  0  0  0
 11 31  1  0  0  0  0
  4  2  1  0  0  0  0
 14 15  1  0  0  0  0
  2  3  2  0  0  0  0
 18 14  1  0  0  0  0
  2  1  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 13 32  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
  7 26  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  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
M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.4787   -3.3822    3.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -3.0391    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -3.8589    0.9968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -1.6942    1.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2740    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120    0.2325    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    1.0136    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    2.5173   -0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6149    3.3051   -1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    2.8387   -2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    3.1119   -3.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673    3.6896   -2.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326    2.2491   -3.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    1.8719   -2.6863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321    0.4918   -2.0717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1879    0.3124   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    0.7478    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498    0.8094   -3.3126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9429    1.0055   -3.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1208   -4.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -2.9025    3.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -4.4654    3.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -3.0639    3.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -1.5706    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -1.7617   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    0.5195   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    2.7546   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    2.9073    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    3.3487   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    4.3537   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    2.7644   -4.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.0049   -4.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    2.6878   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.1878   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -0.7454   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193    0.8727   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.8386    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    0.4115    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.6563   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    1.4661   -4.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    0.0408   -3.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -0.1583   -4.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351    0.7748   -5.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6245   -0.7987   -4.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 18  1  0
 13 14  1  0
  8  9  1  0
  6  7  2  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
 14 33  1  1
  8  7  1  0
 15 34  1  6
 10 11  1  0
  6  5  1  0
  9 10  1  0
 18 19  1  1
 11 12  2  0
 18 20  1  0
 10 13  2  0
  5  4  1  0
 11 31  1  0
  4  2  1  0
 14 15  1  0
  2  3  2  0
 18 14  1  0
  2  1  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 13 32  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
  7 26  1  0
  5 24  1  0
  5 25  1  0
 19 39  1  0
 19 40  1  0
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 20 42  1  0
 20 43  1  0
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  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652306202120563D          

 44 45  0  0  0  0            999 V2000
   -0.4787   -3.3822    3.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -3.0391    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -3.8589    0.9968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -1.6942    1.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2740    0.3418 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2120    0.2325    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    1.0136    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    2.5173   -0.0055 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6149    3.3051   -1.0599 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7458    2.8387   -2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    3.1119   -3.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673    3.6896   -2.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326    2.2491   -3.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    1.8719   -2.6863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321    0.4918   -2.0717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1879    0.3124   -0.6887 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2055    0.7478    0.4178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4498    0.8094   -3.3126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9429    1.0055   -3.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1208   -4.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -2.9025    3.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -4.4654    3.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -3.0639    3.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -1.5706    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -1.7617   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    0.5195   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    2.7546   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    2.9073    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    3.3487   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    4.3537   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    2.7644   -4.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.0049   -4.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    2.6878   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.1878   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -0.7454   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193    0.8727   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.8386    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    0.4115    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.6563   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    1.4661   -4.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    0.0408   -3.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -0.1583   -4.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351    0.7748   -5.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6245   -0.7987   -4.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 18  1  0  0  0  0
 13 14  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  6  1  0  0  0  0
 14 33  1  1  0  0  0
  8  7  1  0  0  0  0
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 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
  9 10  1  0  0  0  0
 18 19  1  1  0  0  0
 11 12  2  0  0  0  0
 18 20  1  0  0  0  0
 10 13  2  0  0  0  0
  5  4  1  0  0  0  0
 11 31  1  0  0  0  0
  4  2  1  0  0  0  0
 14 15  1  0  0  0  0
  2  3  2  0  0  0  0
 18 14  1  0  0  0  0
  2  1  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 13 32  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
  7 26  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  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
M  END
> <DATABASE_ID>
NP0035509

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)C1=C([H])/[C@]2([H])[C@@]([H])(C([H])([H])C([H])([H])\C(=C([H])/C([H])([H])C\1([H])[H])C([H])([H])OC(=O)C([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O3/c1-12(19)20-11-13-5-4-6-14(10-18)9-16-15(8-7-13)17(16,2)3/h5,9-10,15-16H,4,6-8,11H2,1-3H3/b13-5+,14-9+/t15-,16-/m1/s1

> <INCHI_KEY>
VGOHBZXHAWVRBT-ZLMMBQDDSA-N

> <FORMULA>
C17H24O3

> <MOLECULAR_WEIGHT>
276.376

> <EXACT_MASS>
276.172544633

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.47482007142493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4E,8E,10R)-8-formyl-11,11-dimethylbicyclo[8.1.0]undeca-4,8-dien-4-yl]methyl acetate

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
2.6548063216666673

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.479552627024638

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
80.24289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4E,8E,10R)-8-formyl-11,11-dimethylbicyclo[8.1.0]undeca-4,8-dien-4-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.4787   -3.3822    3.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -3.0391    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -3.8589    0.9968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -1.6942    1.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2740    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120    0.2325    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    1.0136    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    2.5173   -0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6149    3.3051   -1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    2.8387   -2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    3.1119   -3.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673    3.6896   -2.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326    2.2491   -3.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    1.8719   -2.6863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321    0.4918   -2.0717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1879    0.3124   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    0.7478    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498    0.8094   -3.3126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9429    1.0055   -3.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1208   -4.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -2.9025    3.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -4.4654    3.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -3.0639    3.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -1.5706    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -1.7617   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    0.5195   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    2.7546   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    2.9073    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    3.3487   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    4.3537   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    2.7644   -4.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.0049   -4.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    2.6878   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.1878   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -0.7454   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193    0.8727   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.8386    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    0.4115    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.6563   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    1.4661   -4.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    0.0408   -3.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -0.1583   -4.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351    0.7748   -5.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6245   -0.7987   -4.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 18  1  0
 13 14  1  0
  8  9  1  0
  6  7  2  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
 14 33  1  1
  8  7  1  0
 15 34  1  6
 10 11  1  0
  6  5  1  0
  9 10  1  0
 18 19  1  1
 11 12  2  0
 18 20  1  0
 10 13  2  0
  5  4  1  0
 11 31  1  0
  4  2  1  0
 14 15  1  0
  2  3  2  0
 18 14  1  0
  2  1  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 13 32  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
  7 26  1  0
  5 24  1  0
  5 25  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
  1 21  1  0
  1 22  1  0
  1 23  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      -0.479  -3.382   3.207  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.014  -3.039   1.825  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.355  -3.859   0.997  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.068  -1.694   1.638  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.371  -1.274   0.342  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.212   0.233   0.252  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.293   1.014   0.037  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.407   2.517  -0.006  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.615   3.305  -1.060  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.746   2.839  -2.486  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.034   3.112  -3.176  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.967   3.690  -2.632  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.233   2.249  -3.203  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.558   1.872  -2.686  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.632   0.492  -2.072  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.188   0.312  -0.689  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.206   0.748   0.418  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.450   0.809  -3.313  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.943   1.006  -3.199  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.045   0.121  -4.595  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.168  -2.902   3.946  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.426  -4.465   3.349  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.516  -3.064   3.339  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.418  -1.571   0.206  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.230  -1.762  -0.435  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.261   0.520  -0.067  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.472   2.755  -0.133  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.151   2.907   0.989  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.438   3.349  -0.766  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.940   4.354  -1.011  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.107   2.764  -4.220  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.046   2.005  -4.246  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.083   2.688  -2.195  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.798  -0.188  -2.231  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.445  -0.745  -0.555  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.119   0.873  -0.554  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.215   1.839   0.483  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.599   0.412   1.385  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.221   1.656  -2.364  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.335   1.466  -4.112  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.442   0.041  -3.060  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.986  -0.158  -4.608  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.235   0.775  -5.452  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.624  -0.799  -4.730  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   24   25                                             
CONECT    6    7   17    5                                                  
CONECT    7    6    8   26                                                  
CONECT    8    9    7   27   28                                             
CONECT    9    8   10   29   30                                             
CONECT   10   11    9   13                                                  
CONECT   11   10   12   31                                                  
CONECT   12   11                                                            
CONECT   13   14   10   32                                                  
CONECT   14   13   33   15   18                                             
CONECT   15   18   16   34   14                                             
CONECT   16   15   17   35   36                                             
CONECT   17   16    6   37   38                                             
CONECT   18   15   19   20   14                                             
CONECT   19   18   39   40   41                                             
CONECT   20   18   42   43   44                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31   11                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   19                                                            
CONECT   40   19                                                            
CONECT   41   19                                                            
CONECT   42   20                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

RDKit          3D

44 45  0  0  0  0  0  0  0  0999 V2000
   -0.4787   -3.3822    3.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135   -3.0391    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554   -3.8589    0.9968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682   -1.6942    1.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2740    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120    0.2325    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    1.0136    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    2.5173   -0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6149    3.3051   -1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    2.8387   -2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338    3.1119   -3.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673    3.6896   -2.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326    2.2491   -3.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    1.8719   -2.6863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321    0.4918   -2.0717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1879    0.3124   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    0.7478    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498    0.8094   -3.3126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9429    1.0055   -3.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1208   -4.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682   -2.9025    3.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -4.4654    3.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -3.0639    3.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -1.5706    0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -1.7617   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    0.5195   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    2.7546   -0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    2.9073    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    3.3487   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    4.3537   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    2.7644   -4.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    2.0049   -4.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    2.6878   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -0.1878   -2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -0.7454   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193    0.8727   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.8386    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    0.4115    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2205    1.6563   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3354    1.4661   -4.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    0.0408   -3.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -0.1583   -4.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351    0.7748   -5.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6245   -0.7987   -4.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 18  1  0
 13 14  1  0
  8  9  1  0
  6  7  2  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
 14 33  1  1
  8  7  1  0
 15 34  1  6
 10 11  1  0
  6  5  1  0
  9 10  1  0
 18 19  1  1
 11 12  2  0
 18 20  1  0
 10 13  2  0
  5  4  1  0
 11 31  1  0
  4  2  1  0
 14 15  1  0
  2  3  2  0
 18 14  1  0
  2  1  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 13 32  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
  7 26  1  0
  5 24  1  0
  5 25  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

View in JSmol

Synonyms

Value	Source
[(1R,4E,8E,10R)-8-Formyl-11,11-dimethylbicyclo[8.1.0]undeca-4,8-dien-4-yl]methyl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₃

Average Mass

276.3760 Da

Monoisotopic Mass

276.17254 Da

IUPAC Name

[(1R,4E,8E,10R)-8-formyl-11,11-dimethylbicyclo[8.1.0]undeca-4,8-dien-4-yl]methyl acetate

Traditional Name

[(1R,4E,8E,10R)-8-formyl-11,11-dimethylbicyclo[8.1.0]undeca-4,8-dien-4-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H]C(=O)C1=C([H])/[C@]2([H])[C@@]([H])(C([H])([H])C([H])([H])\C(=C([H])/C([H])([H])C\1([H])[H])C([H])([H])OC(=O)C([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C17H24O3/c1-12(19)20-11-13-5-4-6-14(10-18)9-16-15(8-7-13)17(16,2)3/h5,9-10,15-16H,4,6-8,11H2,1-3H3/b13-5+,14-9+/t15-,16-/m1/s1

InChI Key

VGOHBZXHAWVRBT-ZLMMBQDDSA-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
Valeriana officinalis var. latifolia	JEOL database	Wang, P. -C., et al, J. Nat. Prod. 73, 1563 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclogermacrane and isolepidozane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the bicyclogermacrane (3,7,11,11-tetramethylbicyclo[8.1.0]Undecane, 9CI) skeleton or the isolepidozane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Bicyclogermacrane and isolepidozane sesquiterpenoids

Alternative Parents

Substituents

Bicyclogermacrane sesquiterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	3.4	ALOGPS
logP	2.65	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.5	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	4	ChemAxon
Refractivity	80.24 m³·mol⁻¹	ChemAxon
Polarizability	31.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58139135

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, P. -C., et al. (2010). Wang, P. -C., et al, J. Nat. Prod. 73, 1563 (2010). J. Nat. Prod..

Showing NP-Card for volvalerenal E (NP0035509)

MOL for NP0035509 (volvalerenal E)

3D MOL for NP0035509 (volvalerenal E)

3D SDF for NP0035509 (volvalerenal E)

3D-SDF for NP0035509 (volvalerenal E)

PDB for NP0035509 (volvalerenal E)

3D PDB for NP0035509 (volvalerenal E)

SMILES for NP0035509 (volvalerenal E)

INCHI for NP0035509 (volvalerenal E)

Structure for NP0035509 (volvalerenal E)

3D Structure for NP0035509 (volvalerenal E)