NP-MRD: Showing NP-Card for methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate (NP0304540)

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Record Information

Version

2.0

Created at

2022-09-10 19:42:26 UTC

Updated at

2022-09-10 19:42:26 UTC

NP-MRD ID

NP0304540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate

Description

Diosbulbinoside F belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate is found in Dioscorea bulbifera. Based on a literature review very few articles have been published on Diosbulbinoside F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221422D          

 38 42  0  0  1  0            999 V2000
    4.0145   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.8743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -4.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.8743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -4.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.1599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025    2.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 35  2  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  0  0  0  0
 26 37  1  0  0  0  0
 10 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
    2.0734    3.4248   -2.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9074    2.8828   -2.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4745    3.8704   -0.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5245    2.6383   -0.1266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5618    3.3178    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948    2.9885    1.8898 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7228    2.8613    3.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6155    1.8442    1.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082    0.6951    0.9833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5300    1.2087    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606    0.3107   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    0.7274   -0.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.0346   -0.6349 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9483    0.0664    0.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850   -0.8777    1.1148 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2662   -0.5731    2.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2069   -1.5117    2.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434   -0.8340    0.2936 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7874   -2.0774    0.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.6274   -1.1605 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1005   -0.3387   -1.8054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    0.4621   -1.3850 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6047    0.5929   -2.7494 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -1.0916    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2605   -1.5346    0.2136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6149   -2.4372   -0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9741   -2.7013   -1.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551   -2.3590    0.1279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1562   -2.6984   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950   -3.8744   -0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8729   -3.8264   -1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2784   -2.6981   -0.5199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3019   -1.9916   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871   -0.9491    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -0.3919    0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4178    0.1258   -1.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539    3.2577   -2.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1367    2.9194   -3.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8696    4.5021   -3.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    2.9629   -0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886    4.3876    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    2.7980    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353    3.9043    1.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    3.2753    3.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867    2.1390    0.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158    1.5225    1.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324    0.2975    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5058   -1.0810   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3916   -1.8671    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7410    0.4336    2.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813   -0.5479    3.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0934   -1.0891    2.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8235   -0.0563    0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -2.7722    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4414   -1.5643   -1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1437   -0.6808   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2884    1.3879   -0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2407   -0.2689   -3.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7816   -1.8240   -0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5366   -2.1008    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4329   -3.0662    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8438   -4.6734   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4150   -4.6271   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6457   -0.9360    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3109    0.8178   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
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  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
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 30 36  1  0
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 37 10  1  0
  1 39  1  0
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 18 54  1  0
 19 55  1  1
 20 56  1  0
 21 57  1  6
 22 58  1  0
 23 59  1  1
 24 60  1  0
M  END


  Mrv1652309102221422D          

 38 42  0  0  1  0            999 V2000
    4.0145   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645   -2.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3020   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025    2.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 35  2  0  0  0  0
 30 36  1  0  0  0  0
 36 37  1  0  0  0  0
 26 37  1  0  0  0  0
 10 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0304540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@H](O)C[C@@H]2C1=C(C[C@@H]1C(=O)O[C@@H](C[C@@]21C)C1=COC=C1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-26-8-17(11-3-4-35-10-11)36-24(33)15(26)7-16(19-13(23(32)34-2)5-12(28)6-14(19)26)37-25-22(31)21(30)20(29)18(9-27)38-25/h3-4,10,12-15,17-18,20-22,25,27-31H,5-9H2,1-2H3/t12-,13+,14+,15+,17-,18+,20+,21-,22+,25+,26-/m0/s1

> <INCHI_KEY>
SVXOFPLAAYAGIG-NDDGLTBUSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.98941162288337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,4aS,7R,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4H,4aH,5H,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

> <JCHEM_LOGP>
-1.4780293376666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.192449735114145

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200274889762051

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7116076695147227

> <JCHEM_POLAR_SURFACE_AREA>
185.35000000000002

> <JCHEM_REFRACTIVITY>
127.18839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,4aS,7R,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4aH,5H,7H,8H,9H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

> <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       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.724  -3.231   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.034  -1.897   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.184  -5.898   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.414  -7.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -8.566   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.414  -9.899   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874  -7.232   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.104  -8.566   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.104  -5.898   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.564  -5.898   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.206   0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.738   3.598   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.058   5.105   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.724   5.875   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.420   4.844   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   37                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27   37                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31                                                       
CONECT   36   30   37                                                       
CONECT   37   36   26   10   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

methyl (2S,4aS,7R,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4H,4aH,5H,7H,8H,9H,10H,10aH,10bH-naphtho[2,1-c]pyran-7-carboxylate

Traditional Name

methyl (2S,4aS,7R,9R,10aS,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,2H,4aH,5H,7H,8H,9H,10H,10aH-naphtho[2,1-c]pyran-7-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C[C@H](O)C[C@@H]2C1=C(C[C@@H]1C(=O)O[C@@H](C[C@@]21C)C1=COC=C1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H34O12/c1-26-8-17(11-3-4-35-10-11)36-24(33)15(26)7-16(19-13(23(32)34-2)5-12(28)6-14(19)26)37-25-22(31)21(30)20(29)18(9-27)38-25/h3-4,10,12-15,17-18,20-22,25,27-31H,5-9H2,1-2H3/t12-,13+,14+,15+,17-,18+,20+,21-,22+,25+,26-/m0/s1

InChI Key

SVXOFPLAAYAGIG-NDDGLTBUSA-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
Dioscorea bulbifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Naphthopyran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Naphthalene
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Pyran
Oxane
Methyl ester
Cyclic alcohol
Furan
Heteroaromatic compound
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxygen compound
Organooxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
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	-1.5	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	185.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.19 m³·mol⁻¹	ChemAxon
Polarizability	52.99 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

158163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

181842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate (NP0304540)

MOL for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D MOL for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D SDF for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D-SDF for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

PDB for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D PDB for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

SMILES for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

INCHI for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

Structure for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)

3D Structure for NP0304540 (methyl (2s,4as,7r,9r,10as,10bs)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,4ah,5h,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-7-carboxylate)