NP-MRD: Showing NP-Card for methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate (NP0228526)

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Record Information

Version

2.0

Created at

2022-09-06 08:13:20 UTC

Updated at

2022-09-06 08:13:20 UTC

NP-MRD ID

NP0228526

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate

Description

Methyl (4aS,4bS,6aS,7S,8R,9R,10S,10aS,10bR,12aS)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-4b-carboxylate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate is found in Galphimia glauca. Based on a literature review very few articles have been published on methyl (4aS,4bS,6aS,7S,8R,9R,10S,10aS,10bR,12aS)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-4b-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210132D          

 40 43  0  0  1  0            999 V2000
    2.5091    0.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -1.7451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -1.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.5204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9690   -2.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6990   -1.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -2.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893   -2.9882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1294   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8764   -2.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593   -1.5850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -0.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6392   -2.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897   -2.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.9236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9395   -4.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -4.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5091   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -3.4559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6990   -4.0796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9690   -4.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -3.9236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3488   -4.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -3.1441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1697   -3.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0233   -2.6261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1042   -1.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7930   -2.9232    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 28  1  1  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 35 38  1  6  0  0  0
 38 39  1  0  0  0  0
 38 40  1  6  0  0  0
M  END

     RDKit          3D

 90 93  0  0  0  0  0  0  0  0999 V2000
   -4.7217    4.3579    4.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4875    3.6367    2.8517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519    2.2835    2.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4280    1.5779    3.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0964    1.5352    1.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497    0.7285    1.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3479   -0.0167    0.4715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0026   -0.7269    0.8280 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1283   -1.8363    1.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1887    0.3598    1.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2872    0.0478    1.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -0.1103    0.2646 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7757    1.1862   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    2.2332    0.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9077    1.4585   -1.7306 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042    2.7068   -2.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635   -0.4386    0.3346 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4266   -1.5556    1.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2011    0.5780    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8044    1.6212    0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1596    2.9156    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.4377   -1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137    0.1952   -1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9963   -0.8505   -0.9326 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1077   -1.8523   -0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1439   -1.6262   -1.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6677   -1.3689   -1.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1397   -1.2269   -0.4040 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3979   -2.5644    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -0.9085   -0.4866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1063   -1.7257   -1.4619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0069   -1.1904   -2.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107   -1.9669   -1.1019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2259   -2.1877   -2.2761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2428   -0.8832   -0.3184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2620   -1.6821    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9875   -2.4463   -0.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992   -0.1095   -1.3108 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3771    0.6626   -2.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9234   -1.0518   -1.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7786    4.6590    4.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    5.2912    3.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043    3.7656    4.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    1.0097    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    2.3448    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005    1.4398    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0403    0.0459    2.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9540    0.7771   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0499   -1.6754    2.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2211   -2.8516    1.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400   -1.7902    2.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4887    0.3754    2.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3751    1.3252    1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488   -0.7200    2.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164    1.0038    2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999    3.1937   -2.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    2.5183   -3.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9802    3.3325   -2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3534   -1.6160    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141    1.0459    1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0873    0.0428    1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1155    3.7531    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769    2.8765    1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4633    3.0891    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025    2.2326   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6950   -0.2329   -2.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140    0.4089   -2.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6850   -2.7621   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6081   -2.1339   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8668   -1.3460    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220   -1.3703   -2.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -2.7389   -1.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999   -0.6183   -2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043   -2.3367   -2.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193   -2.6374    1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993   -3.3144   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3279   -3.0723   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.1420   -0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -2.7578   -1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140   -1.8006   -3.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031   -2.9552   -0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0313   -3.0664   -2.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0234   -1.1338    0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799   -2.4839    1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5241   -3.1061    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8448    0.5466   -0.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271    1.5516   -2.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125    1.0809   -2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3912    0.0723   -3.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6026   -0.6004   -2.5189 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
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 13 14  2  0
 13 15  1  0
 15 16  1  0
 12 28  1  0
 28 29  1  1
 28 27  1  0
 27 26  1  0
 26 24  1  0
 24 25  1  1
 24 23  1  0
 23 22  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  1
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  1
 36 37  1  0
 35 38  1  0
 38 39  1  0
 38 40  1  0
 35  7  1  0
 30  8  1  0
 17 12  1  0
 17 24  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  6
  9 49  1  0
  9 50  1  0
  9 51  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 16 56  1  0
 16 57  1  0
 16 58  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 27 73  1  0
 27 74  1  0
 26 71  1  0
 26 72  1  0
 25 68  1  0
 25 69  1  0
 25 70  1  0
 23 66  1  0
 23 67  1  0
 22 65  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
 19 60  1  0
 19 61  1  0
 18 59  1  0
 30 78  1  6
 31 79  1  6
 32 80  1  0
 33 81  1  1
 34 82  1  0
 36 83  1  0
 36 84  1  0
 37 85  1  0
 38 86  1  1
 39 87  1  0
 39 88  1  0
 39 89  1  0
 40 90  1  0
M  END


  Mrv1652309062210132D          

 40 43  0  0  1  0            999 V2000
    2.5091    0.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -1.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -1.7451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -1.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.5204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9690   -2.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6990   -1.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091   -2.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893   -2.9882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1294   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8764   -2.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593   -1.5850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -0.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6392   -2.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897   -2.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.9236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9395   -4.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -4.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5091   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -3.4559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6990   -4.0796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9690   -4.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -3.9236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3488   -4.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -3.1441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1697   -3.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0233   -2.6261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1042   -1.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7930   -2.9232    0.0000 O   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 28  1  1  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 35 38  1  6  0  0  0
 38 39  1  0  0  0  0
 38 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0228526

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@H]1[C@]2(C)CC[C@]3(C(=O)OC)[C@](C)(CC[C@@]4(C)CC=C(C)C[C@@]34O)[C@H]2[C@H](O)[C@H](O)[C@]1(CO)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O9/c1-18-10-11-26(3)12-14-28(5)23-22(35)24(36)29(17-32,19(2)33)20(8-9-21(34)39-6)27(23,4)13-15-30(28,25(37)40-7)31(26,38)16-18/h10,19-20,22-24,32-33,35-36,38H,8-9,11-17H2,1-7H3/t19-,20+,22+,23+,24+,26-,27+,28-,29-,30+,31+/m1/s1

> <INCHI_KEY>
RBKYLTMXHKKOOD-ISGLCVLNSA-N

> <FORMULA>
C31H50O9

> <MOLECULAR_WEIGHT>
566.732

> <EXACT_MASS>
566.34548319

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
62.27977020242986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4aS,4bS,6aS,7S,8R,9R,10S,10aS,10bR,12aS)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-4b-carboxylate

> <JCHEM_LOGP>
1.2977299959999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.791445927191702

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.209219723334243

> <JCHEM_PKA_STRONGEST_BASIC>
-2.825582689592502

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
148.23340000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4aS,4bS,6aS,7S,8R,9R,10S,10aS,10bR,12aS)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.684   0.243   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.188  -1.212   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.180  -2.377   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.443  -3.258   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -2.086   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.659  -3.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.163  -4.705   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.676  -4.996   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.171  -3.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.684  -3.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.196  -4.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.700  -5.578   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.708  -4.414   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.103  -3.760   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.204  -2.959   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.212  -1.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.212  -5.869   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.660  -4.395   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.220  -4.705   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.733  -4.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.741  -3.832   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.237  -6.451   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.229  -7.615   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.716  -7.324   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.220  -8.779   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.708  -8.488   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.196  -8.197   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.692  -6.742   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.684  -7.906   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.180  -6.451   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.171  -7.615   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.676  -9.070   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.659  -7.324   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.651  -8.488   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.155  -5.869   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.317  -6.322   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.660  -7.823   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.043  -4.902   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.195  -3.381   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.480  -5.457   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9   10   30                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17   28                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   12   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    8   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    7   36   38                                             
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
Methyl (4as,4BS,6as,7S,8R,9R,10S,10as,10BR,12as)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-4b-carboxylic acid	Generator

Chemical Formula

C₃₁H₅₀O₉

Average Mass

566.7320 Da

Monoisotopic Mass

566.34548 Da

IUPAC Name

methyl (4aS,4bS,6aS,7S,8R,9R,10S,10aS,10bR,12aS)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-4b-carboxylate

Traditional Name

methyl (4aS,4bS,6aS,7S,8R,9R,10S,10aS,10bR,12aS)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)CC[C@H]1[C@]2(C)CC[C@]3(C(=O)OC)[C@](C)(CC[C@@]4(C)CC=C(C)C[C@@]34O)[C@H]2[C@H](O)[C@H](O)[C@]1(CO)[C@@H](C)O

InChI Identifier

InChI=1S/C31H50O9/c1-18-10-11-26(3)12-14-28(5)23-22(35)24(36)29(17-32,19(2)33)20(8-9-21(34)39-6)27(23,4)13-15-30(28,25(37)40-7)31(26,38)16-18/h10,19-20,22-24,32-33,35-36,38H,8-9,11-17H2,1-7H3/t19-,20+,22+,23+,24+,26-,27+,28-,29-,30+,31+/m1/s1

InChI Key

RBKYLTMXHKKOOD-ISGLCVLNSA-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 colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
18-hydroxysteroid
12-hydroxysteroid
4-hydroxysteroid
10-hydroxysteroid
Hydroxysteroid
12-alpha-hydroxysteroid
17-hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Steroid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Methyl ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.3	ChemAxon
pKa (Strongest Acidic)	13.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	148.23 m³·mol⁻¹	ChemAxon
Polarizability	62.28 Å³	ChemAxon
Number of Rings	4	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

23338906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566235

PDB ID

Not Available

ChEBI ID

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References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate (NP0228526)

MOL for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

3D MOL for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

3D SDF for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

3D-SDF for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

PDB for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

3D PDB for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

SMILES for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

INCHI for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

Structure for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)

3D Structure for NP0228526 (methyl (4as,4bs,6as,7s,8r,9r,10s,10as,10br,12as)-4a,9,10-trihydroxy-8-[(1r)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate)