NP-MRD: Showing NP-Card for 10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid (NP0330654)

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Record Information

Version

2.0

Created at

2022-09-12 16:12:47 UTC

Updated at

2022-09-12 16:12:47 UTC

NP-MRD ID

NP0330654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

Description

Phytolaccoside D belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Phytolaccoside D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Phytolaccoside D has been detected, but not quantified in, fruits and green vegetables. 10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid is found in Phytolacca acinosa and Phytolacca americana. This could make phytolaccoside D a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307592D          

 57 63  0  0  0  0            999 V2000
   10.5315    3.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4894    0.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3053   -2.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8402    4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184    1.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2039    0.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2039   -1.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0605   -0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -0.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184   -1.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7763    1.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3473   -0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7763    1.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0618   -0.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3473    1.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0592   -2.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171   -0.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2446   -2.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6329    0.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3473    1.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0592   -1.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2026   -0.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4895   -1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2039   -0.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0605   -1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447   -1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447   -0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171   -1.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0592   -0.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -1.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737   -0.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7763    0.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5921    3.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0618    2.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4895   -0.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -1.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6329   -0.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184   -0.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0618    0.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448   -2.9744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269   -3.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -1.7369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -1.7369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697   -0.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171   -2.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0592    0.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7763   -0.4994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4907    0.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4046    2.8768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3099    3.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -0.4994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737   -1.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -0.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -1.7369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6329   -0.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184    0.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 19  5  2  0  0  0  0
 20 15  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  7  1  0  0  0  0
 24  6  1  0  0  0  0
 25  8  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 35  1  1  0  0  0  0
 35 11  1  0  0  0  0
 35 15  1  0  0  0  0
 35 34  1  0  0  0  0
 36  2  1  0  0  0  0
 36  9  1  0  0  0  0
 36 23  1  0  0  0  0
 36 24  1  0  0  0  0
 37  3  1  0  0  0  0
 37 18  1  0  0  0  0
 37 23  1  0  0  0  0
 37 25  1  0  0  0  0
 38 12  1  0  0  0  0
 38 19  1  0  0  0  0
 39 10  1  0  0  0  0
 39 24  1  0  0  0  0
 39 38  1  0  0  0  0
 40 13  1  0  0  0  0
 40 14  1  0  0  0  0
 40 20  1  0  0  0  0
 40 33  1  0  0  0  0
 41 16  1  0  0  0  0
 42 18  1  0  0  0  0
 43 26  1  0  0  0  0
 44 27  1  0  0  0  0
 45 28  1  0  0  0  0
 46 29  1  0  0  0  0
 47 30  1  0  0  0  0
 48 33  2  0  0  0  0
 49 33  1  0  0  0  0
 50 34  2  0  0  0  0
 51  4  1  0  0  0  0
 51 34  1  0  0  0  0
 52 17  1  0  0  0  0
 52 31  1  0  0  0  0
 53 21  1  0  0  0  0
 53 32  1  0  0  0  0
 54 22  1  0  0  0  0
 54 32  1  0  0  0  0
 55 25  1  0  0  0  0
 55 31  1  0  0  0  0
 38 56  1  0  0  0  0
 39 57  1  0  0  0  0
M  END

     RDKit          3D

123129  0  0  0  0  0  0  0  0999 V2000
   -9.8477   -0.8630    2.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1602   -0.2392    1.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0790    1.1401    1.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6513    1.7936    2.4582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3952    1.8857    0.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6488    3.3873    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9349    1.6058   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8611    1.3419   -1.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9971    0.1546   -1.4425 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8067   -1.0373   -1.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3685   -1.8175   -2.6750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9886   -1.4143   -1.1891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7801    0.2020   -2.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7704   -0.8903   -2.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4352   -1.1001   -0.6154 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2486   -2.3168   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0494    0.0546    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3872    0.9195    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9335    0.7998    0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030   -0.6397    0.8863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0216   -0.5571    1.0739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8013   -0.7128    2.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498    0.8009    0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439    0.8850    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   -0.1297    0.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1225   -0.1382    0.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0526    0.1733   -0.3375 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9821   -0.8601   -0.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -0.7325   -1.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6372    0.5601   -1.4483 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7533    0.5996   -0.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9433    0.7795   -1.3443 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8562   -0.2416   -1.1111 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0878   -0.4823    0.2301 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2447   -1.4828    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5581   -1.7936    1.6211 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5099    0.7200    1.0116 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7961    1.1289    0.6803 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5945    1.9072    0.7058 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1018    3.0341    1.3483 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5994    2.0556   -0.8014 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9331    2.0232   -1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7032    1.7242   -1.2012 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3760    2.9147   -1.0894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375    1.4273    0.0304 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9793    2.5173    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.4781    0.3630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7306   -2.3717   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -2.1626    1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135   -3.4138    1.7203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -1.5734    0.2973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6477   -1.4858   -1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388   -1.0328   -1.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128   -1.3637   -0.3262 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.9108    1.6413    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8437   -1.1399    2.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8612   -0.2052    3.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2994   -1.7850    2.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1964    3.5343    1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7501    3.4472    0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2786    4.0303   -0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5249    2.4851   -1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6268    0.7427   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3320    1.0328   -2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2308    2.2127   -2.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0537   -2.3806   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2499    1.1869   -2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0096    0.1955   -3.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1145   -1.8083   -2.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9070   -0.5386   -2.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1945   -2.0577    0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5444   -2.9764   -0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130   -2.8509    0.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8880    1.7867    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665    1.4357    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0167   -0.0742    2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888   -1.7965    2.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8468    1.6257    1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6050    0.3800   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4548   -0.9456   -2.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6552   -1.5459   -1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0142    0.6894   -2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7837    0.8575   -2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1985   -0.9149    0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9279   -2.4273   -0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1230   -1.1091   -0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 68  1  0
M  END


  Mrv0541 05061307592D          

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M  END
> <DATABASE_ID>
NP0330654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(OC6OCC(OC7OC(CO)C(O)C(O)C7O)C(O)C6O)C(C)(CO)C5CCC34C)C2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H66O15/c1-37(36(52)53-6)13-15-42(35(50)51)16-14-40(4)21(22(42)17-37)7-8-26-38(2)11-10-27(39(3,20-44)25(38)9-12-41(26,40)5)57-33-31(48)29(46)24(19-54-33)56-34-32(49)30(47)28(45)23(18-43)55-34/h7,22-34,43-49H,8-20H2,1-6H3,(H,50,51)

> <INCHI_KEY>
NMDFCFOQBAHNPV-UHFFFAOYSA-N

> <FORMULA>
C42H66O15

> <MOLECULAR_WEIGHT>
810.9644

> <EXACT_MASS>
810.440171442

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
88.58293031253886

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.7403125823333345

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.94216057142472

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.52067484801767

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785723758010729

> <JCHEM_POLAR_SURFACE_AREA>
242.12999999999994

> <JCHEM_REFRACTIVITY>
200.74960000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      19.659   5.638   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.980   0.608   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.637  -4.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.102   8.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.648   2.148   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.314   1.378   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.314  -3.242   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.313  -0.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.647  -0.162   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.648  -2.472   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.982   3.688   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.315  -0.932   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.982   2.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.649  -0.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.315   3.688   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.977  -4.782   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.312  -0.162   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.657  -4.422   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.981   1.378   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.315   2.148   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.977  -3.242   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.978  -0.932   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.980  -2.472   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.314  -0.162   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.313  -2.472   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.643  -2.472   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.978  -2.472   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.643  -0.932   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.312  -3.242   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.977  -0.162   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.646  -2.472   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.311  -0.932   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.982   0.608   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.639   5.638   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.649   4.458   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.980  -0.932   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.647  -3.242   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.981  -0.162   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.648  -0.932   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.649   1.378   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.644  -5.552   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      12.184  -5.869   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -0.690  -3.242   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       4.645  -3.242   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -0.690  -0.162   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       7.312  -4.782   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       1.977   1.378   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      21.982  -0.932   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      23.316   1.378   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      23.155   5.370   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      21.112   7.085   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       8.646  -0.932   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       3.311  -2.472   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       4.645  -0.162   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       9.979  -3.242   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      17.981  -1.702   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      16.648   0.608   0.000  0.00  0.00           C+0
CONECT    1   35                                                            
CONECT    2   36                                                            
CONECT    3   37                                                            
CONECT    4   51                                                            
CONECT    5    6   19                                                       
CONECT    6    5   24                                                       
CONECT    7   10   23                                                       
CONECT    8    9   25                                                       
CONECT    9    8   36                                                       
CONECT   10    7   39                                                       
CONECT   11   13   35                                                       
CONECT   12   14   38                                                       
CONECT   13   11   40                                                       
CONECT   14   12   40                                                       
CONECT   15   20   35                                                       
CONECT   16   21   41                                                       
CONECT   17   22   52                                                       
CONECT   18   37   42                                                       
CONECT   19    5   20   38                                                  
CONECT   20   15   19   40                                                  
CONECT   21   16   26   53                                                  
CONECT   22   17   27   54                                                  
CONECT   23    7   36   37                                                  
CONECT   24    6   36   39                                                  
CONECT   25    8   37   55                                                  
CONECT   26   21   28   43                                                  
CONECT   27   22   29   44                                                  
CONECT   28   26   30   45                                                  
CONECT   29   27   31   46                                                  
CONECT   30   28   32   47                                                  
CONECT   31   29   52   55                                                  
CONECT   32   30   53   54                                                  
CONECT   33   40   48   49                                                  
CONECT   34   35   50   51                                                  
CONECT   35    1   11   15   34                                             
CONECT   36    2    9   23   24                                             
CONECT   37    3   18   23   25                                             
CONECT   38   12   19   39   56                                             
CONECT   39   10   24   38   57                                             
CONECT   40   13   14   20   33                                             
CONECT   41   16                                                            
CONECT   42   18                                                            
CONECT   43   26                                                            
CONECT   44   27                                                            
CONECT   45   28                                                            
CONECT   46   29                                                            
CONECT   47   30                                                            
CONECT   48   33                                                            
CONECT   49   33                                                            
CONECT   50   34                                                            
CONECT   51    4   34                                                       
CONECT   52   17   31                                                       
CONECT   53   21   32                                                       
CONECT   54   22   32                                                       
CONECT   55   25   31                                                       
CONECT   56   38                                                            
CONECT   57   39                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  126    0
END

View in JSmol

Synonyms

Value	Source
10-[(3,4-Dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₄₂H₆₆O₁₅

Average Mass

810.9644 Da

Monoisotopic Mass

810.44017 Da

IUPAC Name

10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(OC6OCC(OC7OC(CO)C(O)C(O)C7O)C(O)C6O)C(C)(CO)C5CCC34C)C2C1)C(O)=O

InChI Identifier

InChI=1S/C42H66O15/c1-37(36(52)53-6)13-15-42(35(50)51)16-14-40(4)21(22(42)17-37)7-8-26-38(2)11-10-27(39(3,20-44)25(38)9-12-41(26,40)5)57-33-31(48)29(46)24(19-54-33)56-34-32(49)30(47)28(45)23(18-43)55-34/h7,22-34,43-49H,8-20H2,1-6H3,(H,50,51)

InChI Key

NMDFCFOQBAHNPV-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
Phytolacca acinosa	LOTUS Database	35616633
Phytolacca americana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid
Disaccharide
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Oxane
Methyl ester
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Acetal
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	2.15	ALOGPS
logP	1.74	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.52	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	242.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	200.75 m³·mol⁻¹	ChemAxon
Polarizability	88.58 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0034641

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013164

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

73157052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid (NP0330654)

MOL for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D MOL for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D SDF for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D-SDF for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

PDB for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D PDB for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

SMILES for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

INCHI for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

Structure for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D Structure for NP0330654 (10-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)