NP-MRD: Showing NP-Card for methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate (NP0276901)

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Record Information

Version

2.0

Created at

2022-09-09 01:15:00 UTC

Updated at

2022-09-09 01:15:00 UTC

NP-MRD ID

NP0276901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate

Description

Galphimidin belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate is found in Galphimia glauca. Based on a literature review very few articles have been published on Galphimidin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092203152D          

 44 48  0  0  1  0            999 V2000
   -4.3974   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6849   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9651   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3776   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9651   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0276   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5438   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3349   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8336   -1.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  6  0  0  0
 26 36  1  0  0  0  0
 15 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
  9 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
  2 44  1  0  0  0  0
M  END

     RDKit          3D

 96100  0  0  0  0  0  0  0  0999 V2000
   -6.2176    2.5831   -2.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2878    2.0690   -1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3555    1.9325    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5273    0.4353    0.2128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5936    0.2514    1.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5702   -0.3138    2.2336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5810    0.6921    2.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6900    0.4931    3.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5540   -0.4230   -0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4696   -1.3310   -1.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9304   -1.3889    0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4938   -1.2296    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6245   -0.9849   -0.5003 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7380   -2.1303   -1.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417   -0.6780    0.0214 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.0848   -3.0988    0.4419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6452   -0.7393    0.5354 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7574   -1.4138   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7241   -0.5896   -0.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056   -1.0158   -1.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7733   -0.0399   -1.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0021   -2.2380   -1.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913    0.3145   -0.1761 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7885    1.2477   -0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881    1.9000    0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9958    1.2290    1.3652 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4223    1.0580    1.4538 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2281    1.6570    2.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6949    1.4420    2.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7090    2.4262    3.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -0.0333    1.7221 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3049   -0.9210    2.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -0.1903   -1.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1110   -1.0932   -2.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009    1.0460   -1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    0.7474   -2.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1799    0.3257   -1.0239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0092    1.2440    0.0050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    0.2083   -1.4750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4849   -0.6172   -2.6312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137    1.5448   -2.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4226   -1.3721    1.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3189   -0.3866    1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272   -1.9993   -2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7506   -2.6128   -1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2948   -2.0447    0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7782   -0.0245   -3.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3981    0.9485    0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2896    0.8451   -1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2826    2.9425    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    2.1435   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  7  1  0
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 32 79  1  0
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 32 81  1  0
M  END


  Mrv1652309092203152D          

 44 48  0  0  1  0            999 V2000
   -4.3974   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6849   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9651   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3776   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9651   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0276   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5438   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3349   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8336   -1.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  6  0  0  0
 26 36  1  0  0  0  0
 15 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
  9 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
  2 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0276901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1CC(=C)C[C@]2(O)[C@@]1(C)CC[C@]1(C)[C@H]3[C@H](O)[C@@H](O)[C@]4(COC(C)=O)[C@@H](C)[C@H](CC[C@H]4[C@]3(C)CC[C@@]21O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H52O10/c1-18-15-22(28(39)42-8)30(6)12-13-31(7)26-25(37)27(38)32(17-43-20(3)35)19(2)23(44-21(4)36)9-10-24(32)29(26,5)11-14-33(31,40)34(30,41)16-18/h19,22-27,37-38,40-41H,1,9-17H2,2-8H3/t19-,22+,23-,24-,25-,26-,27+,29-,30-,31+,32+,33-,34-/m0/s1

> <INCHI_KEY>
LEPHNIMCHVHFLZ-SMDOXGPFSA-N

> <FORMULA>
C34H52O10

> <MOLECULAR_WEIGHT>
620.78

> <EXACT_MASS>
620.356047874

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
67.03191563134175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4S,4aS,6aR,6bS,7S,8S,8aS,9R,10S,12aS,12bS,14aS,14bS)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-docosahydropicene-4-carboxylate

> <JCHEM_LOGP>
1.5185992139999984

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.529176414794279

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.859679445631567

> <JCHEM_PKA_STRONGEST_BASIC>
-3.278825547558549

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
158.5965

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,4aS,6aR,6bS,7S,8S,8aS,9R,10S,12aS,12bS,14aS,14bS)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1H-picene-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.208  -1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.438  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.208  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.208  -6.517   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.438  -7.851   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -9.748  -6.517   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -10.518  -7.851   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.898  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -6.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.128  -6.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.588  -6.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.818  -5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.048  -6.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.278  -5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.508  -6.517   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.278  -7.851   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.032  -6.517   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.802  -7.851   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.802  -5.184   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.572  -6.517   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.112  -6.517   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.882  -7.851   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.422  -7.851   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.112  -9.185   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.032  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.802  -2.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.342  -2.516   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.112  -3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.652  -3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.422  -2.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.652  -1.183   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.962  -2.516   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.342  -5.184   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.748  -5.810   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.508  -3.850   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.262  -2.516   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.278  -2.516   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.818  -2.516   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -3.588  -3.850   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.358  -2.516   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -5.128  -3.850   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -5.289  -2.318   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -5.898  -2.516   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   44                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10   11   42                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   40                                             
CONECT   14   13                                                            
CONECT   15   13   16   36                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26   34                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   20   35                                                  
CONECT   35   34                                                            
CONECT   36   26   15   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   13   41   42                                             
CONECT   41   40                                                            
CONECT   42   40    9   43   44                                             
CONECT   43   42                                                            
CONECT   44   42    2                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₅₂O₁₀

Average Mass

620.7800 Da

Monoisotopic Mass

620.35605 Da

IUPAC Name

methyl (4S,4aS,6aR,6bS,7S,8S,8aS,9R,10S,12aS,12bS,14aS,14bS)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-docosahydropicene-4-carboxylate

Traditional Name

methyl (4S,4aS,6aR,6bS,7S,8S,8aS,9R,10S,12aS,12bS,14aS,14bS)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1H-picene-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1CC(=C)C[C@]2(O)[C@@]1(C)CC[C@]1(C)[C@H]3[C@H](O)[C@@H](O)[C@]4(COC(C)=O)[C@@H](C)[C@H](CC[C@H]4[C@]3(C)CC[C@@]21O)OC(C)=O

InChI Identifier

InChI=1S/C34H52O10/c1-18-15-22(28(39)42-8)30(6)12-13-31(7)26-25(37)27(38)32(17-43-20(3)35)19(2)23(44-21(4)36)9-10-24(32)29(26,5)11-14-33(31,40)34(30,41)16-18/h19,22-27,37-38,40-41H,1,9-17H2,2-8H3/t19-,22+,23-,24-,25-,26-,27+,29-,30-,31+,32+,33-,34-/m0/s1

InChI Key

LEPHNIMCHVHFLZ-SMDOXGPFSA-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
Galphimia glauca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
10-hydroxysteroid
Hydroxysteroid
Steroid
Tricarboxylic acid or derivatives
Cyclic alcohol
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.52	ChemAxon
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	158.6 m³·mol⁻¹	ChemAxon
Polarizability	67.03 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

9214578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11039406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate (NP0276901)

MOL for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

3D MOL for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

3D SDF for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

3D-SDF for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

PDB for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

3D PDB for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

SMILES for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

INCHI for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

Structure for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)

3D Structure for NP0276901 (methyl (4s,4as,6ar,6bs,7s,8s,8as,9r,10s,12as,12bs,14as,14bs)-10-(acetyloxy)-8a-[(acetyloxy)methyl]-7,8,14a,14b-tetrahydroxy-4a,6a,9,12b-tetramethyl-2-methylidene-tetradecahydro-1h-picene-4-carboxylate)