NP-MRD: Showing NP-Card for (2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate (NP0173295)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 10:24:22 UTC

Updated at

2022-09-03 10:24:22 UTC

NP-MRD ID

NP0173295

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate

Description

[(2R,3'R,4'aR,5'S,6'R,6'aR,10'aR,10'bR)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-decahydro-1'H-dispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolane]-6'a-yl]methyl 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. (2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate is found in Scutellaria alpina. Based on a literature review very few articles have been published on [(2R,3'R,4'aR,5'S,6'R,6'aR,10'aR,10'bR)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-decahydro-1'H-dispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolane]-6'a-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032212242D          

 36 40  0  0  1  0            999 V2000
    1.6997   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719   -2.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -1.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883   -2.2769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2210   -1.4854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6519   -0.8881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3155    0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365    0.1060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228   -1.2912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2555   -0.4997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864    0.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191    0.8891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919   -1.8885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8246   -1.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3937   -1.6943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9628   -2.2915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7301   -3.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9283   -3.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3592   -2.6800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1265   -3.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574   -2.8742    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3247   -3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229   -3.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -2.4712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3950   -2.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -1.6693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2770   -1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0996   -1.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2938   -2.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0566   -2.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5912   -2.8260    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 31  1  1  0  0  0
 20 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
 20 36  1  0  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
    4.9467    2.5186   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0492    1.6801   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1794    1.6421   -2.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0731    0.9445   -0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1572    0.1090   -1.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -0.5303   -0.2544 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4626    0.4608    0.5143 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2064    1.3976    1.2212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074    1.7310    2.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006    2.7671    3.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182    1.1280    3.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5568    1.1112   -0.3985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2474    2.0359    0.4611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1890    3.3936    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9435    4.2739    1.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5051    3.8546   -0.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4983    0.1662   -1.0611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9594    0.8660   -2.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    0.1873   -0.3509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0685   -0.7767    0.4553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4961   -2.1447    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902   -2.2825   -1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591   -1.1738   -1.3946 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8118   -1.2771   -2.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -1.5746   -0.7917 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1254   -2.5413   -1.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -3.1083   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0653   -2.1341   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797   -1.2555    0.7227 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8239   -1.6643    2.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629   -0.5652    1.7448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9694   -0.4146    1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0990   -1.0015    2.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842   -1.2830    1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1832   -1.8218    1.9186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6061   -0.8382    0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9428    2.6737   -0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5206    3.5176   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520    2.0593    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5948    0.8164   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6964   -0.5487   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -0.0626    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    3.7601    2.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210    2.7836    2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.5817    4.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    1.7212   -1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4112    5.2316    1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989    4.4089    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9602    3.7930    2.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675    0.9033   -3.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9326    0.5063   -2.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1291    1.9362   -2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699   -2.2532    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600   -2.9351    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008   -3.2745   -1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8348   -2.2599   -1.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0474   -0.7432   -3.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6851   -2.3607   -3.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846   -1.0076   -3.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064   -2.2327    0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974   -2.0527   -2.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -3.4156   -1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943   -3.5169   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0060   -3.9920   -0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393   -1.6111   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6539   -2.7641    0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -2.5570    2.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9073   -1.3994    2.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0819   -0.8939    2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165    0.6743    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0161    0.1699    0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9065   -1.5360   -0.4567 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
  6  5  1  6
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  1  6
 17 19  1  0
 20 19  1  6
 20 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 25  6  1  0
 29 31  1  1
 29  6  1  0
 23 17  1  0
 36 20  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  0
  5 41  1  0
  7 42  1  1
 10 43  1  0
 10 44  1  0
 10 45  1  0
 12 46  1  6
 15 47  1  0
 15 48  1  0
 15 49  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 32 69  1  0
 32 70  1  0
 36 71  1  0
 36 72  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  1
 26 61  1  0
 26 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  0
 28 66  1  0
 30 67  1  0
 30 68  1  0
M  END


  Mrv1652309032212242D          

 36 40  0  0  1  0            999 V2000
    1.6997   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719   -2.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -1.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883   -2.2769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2210   -1.4854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6519   -0.8881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3155    0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365    0.1060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228   -1.2912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2555   -0.4997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864    0.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191    0.8891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919   -1.8885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8246   -1.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3937   -1.6943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9628   -2.2915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7301   -3.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9283   -3.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3592   -2.6800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1265   -3.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574   -2.8742    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3247   -3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229   -3.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -2.4712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3950   -2.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -1.6693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2770   -1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0996   -1.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2938   -2.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0566   -2.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5912   -2.8260    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 31  1  1  0  0  0
 20 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
 20 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173295

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]12[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)O[C@]4(COC(=O)C4)CC[C@]3(C)[C@H]1CCC[C@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O10/c1-15(27)31-14-26-18(7-6-8-25(26)13-33-25)22(4)9-10-24(11-19(30)32-12-24)36-23(22,5)20(34-16(2)28)21(26)35-17(3)29/h18,20-21H,6-14H2,1-5H3/t18-,20+,21+,22-,23+,24-,25+,26+/m1/s1

> <INCHI_KEY>
VQKBYMQKRVMNCA-MDNXBFELSA-N

> <FORMULA>
C26H36O10

> <MOLECULAR_WEIGHT>
508.564

> <EXACT_MASS>
508.230847359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.36049685834246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3'R,4'aR,5'S,6'R,6'aR,10'aR,10'bR)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-decahydro-1'H-dispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolane]-6'a-yl]methyl acetate

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
1.1040683016666666

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9264953315033284

> <JCHEM_POLAR_SURFACE_AREA>
126.96000000000001

> <JCHEM_REFRACTIVITY>
120.50549999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3'R,4'aR,5'S,6'R,6'aR,10'aR,10'bR)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolane]-6'a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.173  -2.491   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.597  -3.077   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.801  -4.604   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.817  -2.137   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.241  -2.724   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.445  -4.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.879  -2.773   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.817  -1.658   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.598  -0.165   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.189   0.935   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.095   0.198   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.376  -2.410   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.810  -0.933   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.748   0.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.251  -0.180   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.182   1.660   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.438  -3.525   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.873  -2.048   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.935  -3.163   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.997  -4.278   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.563  -5.755   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.066  -6.118   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.004  -5.003   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.569  -6.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.507  -5.365   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.073  -6.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.576  -7.205   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.514  -6.090   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.948  -4.613   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.471  -4.178   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.586  -3.116   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.584  -2.854   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.119  -2.971   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      15.482  -4.468   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.906  -5.054   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      14.170  -5.275   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                                                       
CONECT    6    5    7   25   29                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   32   36                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23    6   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    6   30   31                                             
CONECT   30   29   31                                                       
CONECT   31   30   29                                                       
CONECT   32   20   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   20                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3'r,4'AR,5's,6'r,6'ar,10'ar,10'BR)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-decahydro-1'H-dispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolane]-6'a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₆O₁₀

Average Mass

508.5640 Da

Monoisotopic Mass

508.23085 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]12[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@]3(C)O[C@]4(COC(=O)C4)CC[C@]3(C)[C@H]1CCC[C@]21CO1

InChI Identifier

InChI=1S/C26H36O10/c1-15(27)31-14-26-18(7-6-8-25(26)13-33-25)22(4)9-10-24(11-19(30)32-12-24)36-23(22,5)20(34-16(2)28)21(26)35-17(3)29/h18,20-21H,6-14H2,1-5H3/t18-,20+,21+,22-,23+,24-,25+,26+/m1/s1

InChI Key

VQKBYMQKRVMNCA-MDNXBFELSA-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
Scutellaria alpina	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
Tetracarboxylic acid or derivatives
Naphthalene
Gamma butyrolactone
Oxane
Pyran
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.44	ALOGPS
logS	-4.5	ALOGPS

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

163002685

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate (NP0173295)

MOL for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

3D MOL for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

3D SDF for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

3D-SDF for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

PDB for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

3D PDB for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

SMILES for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

INCHI for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

Structure for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)

3D Structure for NP0173295 ((2r,3'r,4'ar,5's,6'r,6'ar,10'ar,10'br)-5',6'-bis(acetyloxy)-4'a,10'b-dimethyl-5''-oxo-octahydrodispiro[oxirane-2,7'-naphtho[2,1-b]pyran-3',3''-oxolan]-6'a-ylmethyl acetate)