NP-MRD: Showing NP-Card for 5alpha-hydroxymatricarin (NP0031975)

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Record Information

Version

2.0

Created at

2021-06-19 22:54:27 UTC

Updated at

2021-06-30 00:00:54 UTC

NP-MRD ID

NP0031975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-hydroxymatricarin

Provided By

JEOL Database JEOL Logo

Description

(3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 5alpha-hydroxymatricarin is found in Achillea collina, Achillea collina J. and Achillea collina J.Becker ex Reichenb . 5alpha-hydroxymatricarin was first documented in 2006 (Trendaflova, A., et al.). Based on a literature review very few articles have been published on (3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100543D          

 43 45  0  0  0  0            999 V2000
   -4.7762    0.2251   -1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.0105   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.6531    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.5957   -0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    0.4546    0.0211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5944   -0.8814   -0.3975 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5027   -1.3787    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -2.7072    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -0.6744    0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7837   -1.0467    1.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -2.0328    2.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -0.0083    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840    0.9499    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    2.1454    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.6755    0.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1287    0.5527   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7328    0.4921 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3752    3.0785    0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    3.8767    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    5.0924   -0.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    3.0338   -0.0585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8726    3.5599   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    1.6543   -0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9922    1.2952   -1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046   -0.1800   -2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6381   -0.2857   -0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    0.4665    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -1.6476   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -0.8149   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176   -3.4629    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -3.0951    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -2.6202    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.0740    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    2.2901   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    2.0314    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    3.0498    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -0.0758   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    1.6685    1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    3.0613    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    3.5341   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    4.6022   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001    2.9867   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161    1.6176   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
 23 17  1  0  0  0  0
  7  6  1  0  0  0  0
  9  7  2  0  0  0  0
  6  5  1  0  0  0  0
 15 17  1  0  0  0  0
  9 10  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 21 23  1  0  0  0  0
 10 12  1  0  0  0  0
 19 20  2  0  0  0  0
 12 13  2  0  0  0  0
  5  4  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
  5 23  1  0  0  0  0
  4  2  1  0  0  0  0
  7  8  1  0  0  0  0
  2  1  1  0  0  0  0
 15  9  1  0  0  0  0
  2  3  2  0  0  0  0
 10 11  2  0  0  0  0
 21 22  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  5 27  1  1  0  0  0
 12 33  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 23 43  1  6  0  0  0
 17 38  1  1  0  0  0
 21 39  1  1  0  0  0
 16 37  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 22 42  1  0  0  0  0
M  END

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -4.7762    0.2251   -1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.0105   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.6531    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.5957   -0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    0.4546    0.0211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5944   -0.8814   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -1.3787    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -2.7072    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -0.6744    0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7837   -1.0467    1.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -2.0328    2.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -0.0083    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840    0.9499    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    2.1454    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.6755    0.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1287    0.5527   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7328    0.4921 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3752    3.0785    0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    3.8767    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    5.0924   -0.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    3.0338   -0.0585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8726    3.5599   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    1.6543   -0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9922    1.2952   -1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046   -0.1800   -2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6381   -0.2857   -0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    0.4665    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -1.6476   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -0.8149   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176   -3.4629    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -3.0951    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -2.6202    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.0740    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    2.2901   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    2.0314    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    3.0498    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -0.0758   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    1.6685    1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    3.0613    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    3.5341   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    4.6022   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001    2.9867   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161    1.6176   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 23 17  1  0
  7  6  1  0
  9  7  2  0
  6  5  1  0
 15 17  1  0
  9 10  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 21 23  1  0
 10 12  1  0
 19 20  2  0
 12 13  2  0
  5  4  1  0
 13 15  1  0
 15 16  1  6
  5 23  1  0
  4  2  1  0
  7  8  1  0
  2  1  1  0
 15  9  1  0
  2  3  2  0
 10 11  2  0
 21 22  1  0
  6 28  1  0
  6 29  1  0
  5 27  1  1
 12 33  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 23 43  1  6
 17 38  1  1
 21 39  1  1
 16 37  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END


  Mrv1652306202100543D          

 43 45  0  0  0  0            999 V2000
   -4.7762    0.2251   -1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.0105   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.6531    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.5957   -0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    0.4546    0.0211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5944   -0.8814   -0.3975 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5027   -1.3787    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -2.7072    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -0.6744    0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7837   -1.0467    1.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -2.0328    2.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -0.0083    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840    0.9499    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    2.1454    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.6755    0.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1287    0.5527   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7328    0.4921 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3752    3.0785    0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    3.8767    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    5.0924   -0.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    3.0338   -0.0585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8726    3.5599   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    1.6543   -0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9922    1.2952   -1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046   -0.1800   -2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6381   -0.2857   -0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    0.4665    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -1.6476   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -0.8149   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176   -3.4629    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -3.0951    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -2.6202    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.0740    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    2.2901   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    2.0314    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    3.0498    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -0.0758   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    1.6685    1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    3.0613    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    3.5341   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    4.6022   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001    2.9867   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161    1.6176   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
 23 17  1  0  0  0  0
  7  6  1  0  0  0  0
  9  7  2  0  0  0  0
  6  5  1  0  0  0  0
 15 17  1  0  0  0  0
  9 10  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 21 23  1  0  0  0  0
 10 12  1  0  0  0  0
 19 20  2  0  0  0  0
 12 13  2  0  0  0  0
  5  4  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
  5 23  1  0  0  0  0
  4  2  1  0  0  0  0
  7  8  1  0  0  0  0
  2  1  1  0  0  0  0
 15  9  1  0  0  0  0
  2  3  2  0  0  0  0
 10 11  2  0  0  0  0
 21 22  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  5 27  1  1  0  0  0
 12 33  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 23 43  1  6  0  0  0
 17 38  1  1  0  0  0
 21 39  1  1  0  0  0
 16 37  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 22 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=C([H])C(=O)C1=C(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]1([H])[C@]2([H])OC(=O)[C@@]1([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O6/c1-7-5-12(22-10(4)18)13-9(3)16(20)23-15(13)17(21)8(2)6-11(19)14(7)17/h6,9,12-13,15,21H,5H2,1-4H3/t9-,12-,13+,15-,17+/m0/s1

> <INCHI_KEY>
QFIKHFIONONHSR-OTHHFONVSA-N

> <FORMULA>
C17H20O6

> <MOLECULAR_WEIGHT>
320.341

> <EXACT_MASS>
320.125988364

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.77736007114038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.7929696280000003

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.459520285017657

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9100058273332765

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
80.5816

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -4.7762    0.2251   -1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.0105   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.6531    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.5957   -0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    0.4546    0.0211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5944   -0.8814   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -1.3787    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -2.7072    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -0.6744    0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7837   -1.0467    1.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -2.0328    2.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -0.0083    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840    0.9499    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    2.1454    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.6755    0.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1287    0.5527   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7328    0.4921 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3752    3.0785    0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    3.8767    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    5.0924   -0.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    3.0338   -0.0585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8726    3.5599   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    1.6543   -0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9922    1.2952   -1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046   -0.1800   -2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6381   -0.2857   -0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    0.4665    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -1.6476   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -0.8149   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176   -3.4629    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -3.0951    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -2.6202    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.0740    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    2.2901   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    2.0314    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    3.0498    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -0.0758   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    1.6685    1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    3.0613    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    3.5341   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    4.6022   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001    2.9867   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161    1.6176   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 23 17  1  0
  7  6  1  0
  9  7  2  0
  6  5  1  0
 15 17  1  0
  9 10  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 21 23  1  0
 10 12  1  0
 19 20  2  0
 12 13  2  0
  5  4  1  0
 13 15  1  0
 15 16  1  6
  5 23  1  0
  4  2  1  0
  7  8  1  0
  2  1  1  0
 15  9  1  0
  2  3  2  0
 10 11  2  0
 21 22  1  0
  6 28  1  0
  6 29  1  0
  5 27  1  1
 12 33  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 23 43  1  6
 17 38  1  1
 21 39  1  1
 16 37  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 22 40  1  0
 22 41  1  0
 22 42  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      -4.776   0.225  -1.014  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.571  -0.011  -0.157  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.572  -0.653   0.883  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.481   0.596  -0.706  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.241   0.455   0.021  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.594  -0.881  -0.398  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.503  -1.379   0.523  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.179  -2.707   1.161  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.639  -0.674   0.713  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.784  -1.047   1.601  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.898  -2.033   2.302  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.817  -0.008   1.513  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.384   0.950   0.686  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.189   2.145   0.298  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.008   0.676   0.123  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.129   0.553  -1.292  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.931   1.733   0.492  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.375   3.079   0.255  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.290   3.877   0.040  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.348   5.092  -0.036  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.958   3.034  -0.059  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.873   3.560  -1.155  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.354   1.654  -0.332  0.00  0.00           C+0
HETATM   24  H   UNK     0      -4.992   1.295  -1.063  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.605  -0.180  -2.014  0.00  0.00           H+0
HETATM   26  H   UNK     0      -5.638  -0.286  -0.575  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.444   0.467   1.100  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.378  -1.648  -0.465  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.214  -0.815  -1.425  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.018  -3.463   0.385  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.950  -3.095   1.825  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.739  -2.620   1.752  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.755  -0.074   2.038  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.174   2.290  -0.787  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.237   2.031   0.596  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.811   3.050   0.781  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.849  -0.076  -1.474  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.716   1.669   1.569  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.463   3.061   0.914  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.381   3.534  -2.134  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.149   4.602  -0.960  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.800   2.987  -1.222  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.116   1.618  -1.406  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   23   27                                             
CONECT    6    7    5   28   29                                             
CONECT    7    6    9    8                                                  
CONECT    8    7   30   31   32                                             
CONECT    9    7   10   15                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   13   33                                                  
CONECT   13   14   12   15                                                  
CONECT   14   13   34   35   36                                             
CONECT   15   17   13   16    9                                             
CONECT   16   15   37                                                       
CONECT   17   23   15   18   38                                             
CONECT   18   17   19                                                       
CONECT   19   18   21   20                                                  
CONECT   20   19                                                            
CONECT   21   19   23   22   39                                             
CONECT   22   21   40   41   42                                             
CONECT   23   17   21    5   43                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    5                                                            
CONECT   28    6                                                            
CONECT   29    6                                                            
CONECT   30    8                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33   12                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   16                                                            
CONECT   38   17                                                            
CONECT   39   21                                                            
CONECT   40   22                                                            
CONECT   41   22                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
   -4.7762    0.2251   -1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.0105   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.6531    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    0.5957   -0.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    0.4546    0.0211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5944   -0.8814   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027   -1.3787    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -2.7072    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388   -0.6744    0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7837   -1.0467    1.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -2.0328    2.3020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -0.0083    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840    0.9499    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    2.1454    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.6755    0.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1287    0.5527   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9313    1.7328    0.4921 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3752    3.0785    0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    3.8767    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    5.0924   -0.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    3.0338   -0.0585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8726    3.5599   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535    1.6543   -0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9922    1.2952   -1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046   -0.1800   -2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6381   -0.2857   -0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    0.4665    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -1.6476   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -0.8149   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176   -3.4629    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -3.0951    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -2.6202    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.0740    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741    2.2901   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    2.0314    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    3.0498    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492   -0.0758   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    1.6685    1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    3.0613    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811    3.5341   -2.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    4.6022   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001    2.9867   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161    1.6176   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 23 17  1  0
  7  6  1  0
  9  7  2  0
  6  5  1  0
 15 17  1  0
  9 10  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 21 23  1  0
 10 12  1  0
 19 20  2  0
 12 13  2  0
  5  4  1  0
 13 15  1  0
 15 16  1  6
  5 23  1  0
  4  2  1  0
  7  8  1  0
  2  1  1  0
 15  9  1  0
  2  3  2  0
 10 11  2  0
 21 22  1  0
  6 28  1  0
  6 29  1  0
  5 27  1  1
 12 33  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 23 43  1  6
 17 38  1  1
 21 39  1  1
 16 37  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3S,3AR,4S,9ar,9BS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₆

Average Mass

320.3410 Da

Monoisotopic Mass

320.12599 Da

IUPAC Name

(3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

(3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C(=C([H])C(=O)C1=C(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]1([H])[C@]2([H])OC(=O)[C@@]1([H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C17H20O6/c1-7-5-12(22-10(4)18)13-9(3)16(20)23-15(13)17(21)8(2)6-11(19)14(7)17/h6,9,12-13,15,21H,5H2,1-4H3/t9-,12-,13+,15-,17+/m0/s1

InChI Key

QFIKHFIONONHSR-OTHHFONVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 250 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, 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, 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
Achillea collina	LOTUS Database	35616633
Achillea collina J.	JEOL database	Trendaflova, A., et al, Phytochemistry 67, 764 (2006)
Achillea collina J.Becker ex Reichenb	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.9	ALOGPS
logP	0.79	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.58 m³·mol⁻¹	ChemAxon
Polarizability	32.78 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

32679301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76764466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Trendaflova, A., et al. (2006). Trendaflova, A., et al, Phytochemistry 67, 764 (2006). Phytochem..

Showing NP-Card for 5alpha-hydroxymatricarin (NP0031975)

MOL for NP0031975 (5alpha-hydroxymatricarin)

3D MOL for NP0031975 (5alpha-hydroxymatricarin)

3D SDF for NP0031975 (5alpha-hydroxymatricarin)

3D-SDF for NP0031975 (5alpha-hydroxymatricarin)

PDB for NP0031975 (5alpha-hydroxymatricarin)

3D PDB for NP0031975 (5alpha-hydroxymatricarin)

SMILES for NP0031975 (5alpha-hydroxymatricarin)

INCHI for NP0031975 (5alpha-hydroxymatricarin)

Structure for NP0031975 (5alpha-hydroxymatricarin)

3D Structure for NP0031975 (5alpha-hydroxymatricarin)