NP-MRD: Showing NP-Card for 5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate (NP0188646)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 05:00:31 UTC

Updated at

2022-09-04 05:00:32 UTC

NP-MRD ID

NP0188646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate

Description

5A,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate is found in Aspergillus fumigatus. 5A,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171514252D          

 33 37  0  0  0  0            999 V2000
   -5.1139   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0337   -3.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932   -1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -3.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5570   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8271   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5231   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4473   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2575   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8777   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377   -3.3098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5275   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676   -3.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532   -2.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 13 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 10 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
   -7.4251    1.3436   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3242    0.3818   -0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4795   -0.5708   -1.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1071    0.5067    0.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968   -0.3764   -0.2029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6860   -1.0628    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894   -1.5175    1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2643   -0.4624    0.8367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4575    0.6807    1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141   -0.1972   -0.5792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4383    0.3140   -1.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5171   -0.8766   -1.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612   -1.6850   -0.2631 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1857   -3.1110   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -1.8571   -0.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9121   -0.8105    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2107   -0.7076   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596    0.3860    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3337    0.5503   -0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0558    1.6580    0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3710    1.8401   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    0.9099   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2563   -0.1610   -1.5303 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9604   -0.3503   -1.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118    1.3116    0.9380 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1931    1.2501    1.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    2.1482    2.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020    0.1513    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0251    0.0609    1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1460   -0.9762    0.9696 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9192    0.4689   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593    1.8944   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1247    0.3719   -2.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0776    2.3798   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1303    1.2717   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9837    1.0324    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3900   -1.1232   -0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1125   -0.4852    1.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3172   -2.0087    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.4221    0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1559   -1.7060    2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254    0.4465    2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012    1.6748    1.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    0.6994    2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149   -1.2172   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444    0.6001   -2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0676    1.1698   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4682   -0.4330   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1296   -1.4946   -2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625   -3.2939   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366   -3.4657    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847   -3.8185   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5572   -1.4944   -0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5887    2.3913    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9238    2.7136   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0110    1.0363   -1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188   -1.2302   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340    1.1034    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1422   -0.0607    2.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0702   -1.8054    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071    2.0672    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8614    2.3297   -1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788    2.5186   -0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7040   -0.5927   -2.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2077    0.4580   -2.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6253    1.2530   -2.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 28  2  0
 28 29  1  0
 29 30  1  0
 28 26  1  0
 26 27  2  0
 26 25  1  0
 25 18  1  0
 18 17  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 10 31  1  0
 31 32  1  0
 31 33  1  0
 31  5  1  0
 30  8  1  0
 24 19  1  0
 30 13  1  0
 17 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  6
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  6
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 14 50  1  0
 14 51  1  0
 14 52  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  1
 17 53  1  0
 20 54  1  0
 21 55  1  0
 22 56  1  0
 24 57  1  0
 32 61  1  0
 32 62  1  0
 32 63  1  0
 33 64  1  0
 33 65  1  0
 33 66  1  0
M  END


  Mrv1533004171514252D          

 33 37  0  0  0  0            999 V2000
   -5.1139   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0337   -3.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932   -1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -3.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5570   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8271   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5231   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4473   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2575   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8777   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377   -3.3098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5275   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676   -3.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532   -2.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 13 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 10 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2(C)C(CCC3(C)OC4=C(CC23)C(=O)OC(=C4)C2=CC=CN=C2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H33NO5/c1-16(29)31-23-9-10-26(4)21(25(23,2)3)8-11-27(5)22(26)13-18-20(33-27)14-19(32-24(18)30)17-7-6-12-28-15-17/h6-7,12,14-15,21-23H,8-11,13H2,1-5H3

> <INCHI_KEY>
SDKNSMCWHHTGRG-UHFFFAOYSA-N

> <FORMULA>
C27H33NO5

> <MOLECULAR_WEIGHT>
451.563

> <EXACT_MASS>
451.235873167

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.5849553338633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
3.5690216889999986

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.2064649808646095

> <JCHEM_POLAR_SURFACE_AREA>
74.72

> <JCHEM_REFRACTIVITY>
125.0059

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -9.546  -4.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.034  -4.432   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.530  -5.887   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -7.026  -3.268   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.513  -3.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.505  -2.395   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.993  -2.686   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.489  -4.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.481  -2.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.497  -5.305   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.993  -6.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.481  -7.051   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.472  -5.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.032  -7.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.040  -6.178   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.048  -5.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.544  -3.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.032  -3.268   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.977  -4.432   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.552  -2.395   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.048  -0.940   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.064  -2.686   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.568  -4.141   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.560  -5.305   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.081  -4.432   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.089  -3.268   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.601  -3.559   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.105  -5.014   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       8.097  -6.178   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       6.585  -5.887   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.009  -5.014   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.353  -6.515   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.446  -5.569   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    8   13                                                  
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   16                                                       
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   10    5   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
5a,8,8,11a-Tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₃NO₅

Average Mass

451.5630 Da

Monoisotopic Mass

451.23587 Da

IUPAC Name

5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate

Traditional Name

5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2(C)C(CCC3(C)OC4=C(CC23)C(=O)OC(=C4)C2=CC=CN=C2)C1(C)C

InChI Identifier

InChI=1S/C27H33NO5/c1-16(29)31-23-9-10-26(4)21(25(23,2)3)8-11-27(5)22(26)13-18-20(33-27)14-19(32-24(18)30)17-7-6-12-28-15-17/h6-7,12,14-15,21-23H,8-11,13H2,1-5H3

InChI Key

SDKNSMCWHHTGRG-UHFFFAOYSA-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
Aspergillus fumigatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Alkyl aryl ether
Pyranone
Pyran
Pyridine
Heteroaromatic compound
Vinylogous ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Azacycle
Oxacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
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	5.18	ALOGPS
logP	3.57	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	125.01 m³·mol⁻¹	ChemAxon
Polarizability	50.58 Å³	ChemAxon
Number of Rings	5	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

77387029

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate (NP0188646)

MOL for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D MOL for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D SDF for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D-SDF for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

PDB for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D PDB for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

SMILES for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

INCHI for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

Structure for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D Structure for NP0188646 (5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)