NP-MRD: Showing NP-Card for (2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione (NP0296476)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 06:04:27 UTC

Updated at

2022-09-10 06:04:27 UTC

NP-MRD ID

NP0296476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

Description

15-Deoxyoxalicine B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione is found in Penicillium thiersii. (2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione was first documented in 2003 (PMID: 12605512). Based on a literature review a small amount of articles have been published on 15-Deoxyoxalicine B (PMID: 30123464) (PMID: 30090271).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208042D          

 37 42  0  0  1  0            999 V2000
    1.2235   -6.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714   -6.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923   -6.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829   -5.2216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1415   -5.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685   -5.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0794   -4.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9046   -4.1126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5740   -4.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -3.8609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9442   -3.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407   -2.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515   -2.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -3.5581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7736   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5986   -4.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8503   -3.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -3.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2111   -3.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0174   -3.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2692   -3.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0754   -2.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6299   -3.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3782   -4.2501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5719   -4.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9593   -4.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -4.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -5.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809   -3.0705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081   -4.4154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1028   -4.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884   -4.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -3.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488   -3.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -3.3573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3333   -3.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
 18 30  1  0  0  0  0
 15 30  1  6  0  0  0
 10 31  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 31 37  1  0  0  0  0
M  END

     RDKit          3D

 70 75  0  0  0  0  0  0  0  0999 V2000
   -4.8285   -1.2373    0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3155   -1.1058   -0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0711   -1.9657   -1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -0.3171   -1.3199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5834    0.1379   -2.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974   -1.3299   -1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -1.6099   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377   -0.6133    0.4322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6164   -1.1181    1.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886    0.7174   -0.0976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7850    1.9006    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    1.5614    1.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    0.4109    2.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    0.0642    3.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5462   -0.4699    0.8439 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1873   -1.7827    1.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -1.5057    0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -0.3712    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    0.0851   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0194   -0.5744   -0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3435   -0.1344   -0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5564    0.9764   -1.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8525    1.3301   -1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9454    0.5959   -1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7124   -0.4826   -0.4559 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4748   -0.8316   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9198   -1.6466    0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7893   -2.1376    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628   -3.1739    1.8478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    0.0772   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    0.8841   -0.6276 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5051    2.0350   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7545    2.8075   -1.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0090    2.1495   -1.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0639    2.1609   -2.2119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9602    1.4732   -0.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6476    1.5548    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7002   -1.9055    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4655   -0.7598    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -2.9467   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960   -1.4482   -2.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1368   -2.0276   -1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830   -0.4621   -3.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5582   -0.9790   -2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630   -2.2813   -2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2479   -2.6450   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0508   -1.7408   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9100   -1.5968    2.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2648   -1.9723    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2887   -0.4020    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    0.7472   -1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0024    2.4989    0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5595    2.6938    0.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    2.2782    2.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1245    0.8949    4.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810   -0.8421    3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3556   -0.0158    3.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -2.5919    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -2.1076    2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    0.9684   -1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7453    1.5699   -1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0354    2.1980   -2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9380    0.8591   -1.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3486   -1.7182    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277    2.7373   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    1.6133   -2.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7127    3.8054   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8302    3.0911   -2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6929    1.2878    1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4926    2.6849    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 30  1  0
 18 19  1  0
 19 20  2  0
 20 27  1  0
 27 28  1  0
 28 29  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 10 31  1  0
 31 32  1  6
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 31  4  1  0
 37 31  1  0
 15  8  1  0
 15 30  1  6
 26 21  1  0
 28 17  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  1 38  1  0
  1 39  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  7 47  1  0
  9 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  6
 11 52  1  0
 11 53  1  0
 12 54  1  0
 14 55  1  0
 14 56  1  0
 14 57  1  0
 16 58  1  0
 16 59  1  0
 19 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 26 64  1  0
 32 65  1  0
 32 66  1  0
 33 67  1  0
 33 68  1  0
 37 69  1  0
 37 70  1  0
M  END


  Mrv1652309102208042D          

 37 42  0  0  1  0            999 V2000
    1.2235   -6.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714   -6.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923   -6.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829   -5.2216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1415   -5.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685   -5.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0794   -4.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9046   -4.1126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5740   -4.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190   -3.8609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9442   -3.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407   -2.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515   -2.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -3.5581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7736   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5986   -4.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8503   -3.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -3.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2111   -3.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0174   -3.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2692   -3.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0754   -2.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6299   -3.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3782   -4.2501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5719   -4.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9593   -4.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -4.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -5.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809   -3.0705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081   -4.4154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1028   -4.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884   -4.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -3.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8488   -3.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -3.3573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3333   -3.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
 18 30  1  0  0  0  0
 15 30  1  6  0  0  0
 10 31  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 31 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@]1(O)CC[C@]2(C)[C@H](CC=C(C)[C@@]22CC3=C(O2)C=C(OC3=O)C2=CC=CN=C2)[C@@]11CCC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C30H33NO6/c1-18(2)29(34)12-11-27(4)24(28(29)10-9-25(32)35-17-28)8-7-19(3)30(27)15-21-23(37-30)14-22(36-26(21)33)20-6-5-13-31-16-20/h5-7,13-14,16,24,34H,1,8-12,15,17H2,2-4H3/t24-,27+,28-,29+,30-/m0/s1

> <INCHI_KEY>
FIWRZQROYVDBSG-GBLYIOFISA-N

> <FORMULA>
C30H33NO6

> <MOLECULAR_WEIGHT>
503.595

> <EXACT_MASS>
503.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
54.46730532467999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4'aS,5'R,6'R,8'aR)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-3,4,4',4'a,6',7',8',8'a-octahydrodispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

> <JCHEM_LOGP>
2.885107059000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.778138565026524

> <JCHEM_PKA_STRONGEST_BASIC>
4.206447354349612

> <JCHEM_POLAR_SURFACE_AREA>
94.95

> <JCHEM_REFRACTIVITY>
138.88059999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4'aS,5'R,6'R,8'aR)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3H-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.284 -12.216   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.067 -11.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.359 -11.856   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.275  -9.747   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.264  -9.807   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.741 -10.217   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.882  -9.182   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.555  -7.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.805  -8.577   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.089  -7.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.762  -5.702   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.903  -4.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.369  -5.137   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.510  -4.102   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.696  -6.642   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.177  -8.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.717  -8.098   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.187  -6.632   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.692  -6.306   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.727  -7.446   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.232  -7.120   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.702  -5.653   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.207  -5.327   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.243  -6.467   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      13.773  -7.934   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      12.268  -8.260   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.257  -8.912   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.752  -9.239   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.282 -10.705   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.938  -5.732   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.948  -8.242   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.192  -9.277   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.658  -8.807   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.985  -7.302   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.451  -6.832   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.844  -6.267   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.622  -6.737   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   31                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16   30                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   20   28                                                       
CONECT   28   27   17   29                                                  
CONECT   29   28                                                            
CONECT   30   18   15                                                       
CONECT   31   10    4   32   37                                             
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₃NO₆

Average Mass

503.5950 Da

Monoisotopic Mass

503.23079 Da

IUPAC Name

(2S,4'aS,5'R,6'R,8'aR)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-3,4,4',4'a,6',7',8',8'a-octahydrodispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

Traditional Name

(2S,4'aS,5'R,6'R,8'aR)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3H-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione

CAS Registry Number

Not Available

SMILES

CC(=C)[C@]1(O)CC[C@]2(C)[C@H](CC=C(C)[C@@]22CC3=C(O2)C=C(OC3=O)C2=CC=CN=C2)[C@@]11CCC(=O)OC1

InChI Identifier

InChI=1S/C30H33NO6/c1-18(2)29(34)12-11-27(4)24(28(29)10-9-25(32)35-17-28)8-7-19(3)30(27)15-21-23(37-30)14-22(36-26(21)33)20-6-5-13-31-16-20/h5-7,13-14,16,24,34H,1,8-12,15,17H2,2-4H3/t24-,27+,28-,29+,30-/m0/s1

InChI Key

FIWRZQROYVDBSG-GBLYIOFISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 thiersii	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Alkyl aryl ether
Delta valerolactone
Delta_valerolactone
Pyranone
Pyridine
Pyran
Oxane
Vinylogous ester
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Carboxylic acid ester
Lactone
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organopnictogen compound
Organonitrogen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.89	ChemAxon
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	138.88 m³·mol⁻¹	ChemAxon
Polarizability	54.47 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

9235368

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11060212

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang Y, Li C, Swenson DC, Gloer JB, Wicklow DT, Dowd PF: Novel antiinsectan oxalicine alkaloids from two undescribed fungicolous Penicillium spp. Org Lett. 2003 Mar 6;5(5):773-6. doi: 10.1021/ol0340686. [PubMed:12605512 ]
Yaegashi J, Romsdahl J, Chiang YM, Wang CCC: Correction: Genome mining and molecular characterization of the biosynthetic gene cluster of a diterpenic meroterpenoid, 15-deoxyoxalicine B, in Penicillium canescens. Chem Sci. 2016 Mar 1;7(3):2440. doi: 10.1039/c6sc90012g. Epub 2016 Feb 3. [PubMed:30123464 ]
Yaegashi J, Romsdahl J, Chiang YM, Wang CCC: Genome mining and molecular characterization of the biosynthetic gene cluster of a diterpenic meroterpenoid, 15-deoxyoxalicine B, in Penicillium canescens. Chem Sci. 2015 Nov 1;6(11):6537-6544. doi: 10.1039/c5sc01965f. Epub 2015 Aug 6. [PubMed:30090271 ]
LOTUS database [Link]

Showing NP-Card for (2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione (NP0296476)

MOL for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

3D MOL for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

3D SDF for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

3D-SDF for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

PDB for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

3D PDB for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

SMILES for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

INCHI for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

Structure for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)

3D Structure for NP0296476 ((2s,4'as,5'r,6'r,8'ar)-6'-hydroxy-2',8'a-dimethyl-6'-(prop-1-en-2-yl)-6-(pyridin-3-yl)-4',4'a,7',8'-tetrahydro-3h-dispiro[furo[3,2-c]pyran-2,1'-naphthalene-5',3''-oxane]-4,6''-dione)