NP-MRD: Showing NP-Card for methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate (NP0282557)

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Record Information

Version

2.0

Created at

2022-09-09 09:26:13 UTC

Updated at

2022-09-09 09:26:14 UTC

NP-MRD ID

NP0282557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate

Description

Methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]Tricos-12-ene-20-carboxylate belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate is found in Prunella vulgaris. Based on a literature review very few articles have been published on methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]Tricos-12-ene-20-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092211262D          

 45 50  0  0  0  0            999 V2000
   -1.2375   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8375   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1377   -1.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2192   -2.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440   -2.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3007   -3.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9327   -3.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -3.7287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 30 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 16 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 13 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
  5 44  1  0  0  0  0
 42 45  1  0  0  0  0
 13 45  1  0  0  0  0
M  END

     RDKit          3D

 99104  0  0  0  0  0  0  0  0999 V2000
    4.5540    0.7529    3.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7918    0.6287    2.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9693   -0.0937    1.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9653   -0.6774    2.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972   -0.1676    0.2485 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6822   -0.7925    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6403   -2.2374   -0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430   -2.4186   -1.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1266   -2.1532   -2.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -3.8345   -1.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8632   -1.4782   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -1.0904   -0.4493 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9850   -0.5184   -0.4725 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9441   -1.2253    0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172   -0.6250    0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1143    0.8435    0.9359 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6781    1.6009   -0.0537 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3527    2.7377    0.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539    2.1526   -1.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5091    2.0164   -1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0684    0.9061   -0.4158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5095    0.6613   -0.6092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3211    1.8414   -1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.3571   -1.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9239   -1.5023   -1.3611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983   -2.6401   -2.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0185   -3.8357   -1.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -2.7164   -3.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1165   -0.0443    0.5662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4428   -0.4118    0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8945   -1.6876    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3157   -2.0855    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0571   -2.5930    0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8364    0.6377    1.8794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4216    1.8648    2.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3578    2.0747    3.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9622    3.4328    3.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6815    1.1235    3.8181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    0.6558    2.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    1.2661    0.9502 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6749    2.7666    1.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606    0.8651   -0.6713 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0840    1.6827   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269    1.2322   -0.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -0.0234   -1.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798    1.4156    4.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4878    1.1896    4.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837   -0.2777    4.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566   -0.2289   -0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2367   -0.7148    1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754   -2.8871    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7021   -2.5753   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9229   -2.8884   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574   -2.2108   -3.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7782   -4.1114   -1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547   -3.9119   -2.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0546   -1.9898   -2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154   -0.6388   -2.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -2.0486    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -2.3329    0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7424   -1.2873    1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2104    1.1083    2.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4305    3.6623    0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    3.2445   -1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3554    1.7828   -2.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    1.7197   -2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951    2.9554   -1.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2832    1.4038   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7019   -0.5757   -1.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5226   -4.1574   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8239   -2.0233    1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4325   -3.0610   -0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4507   -0.2067   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2175   -0.1568   -2.6960 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
  5  3  1  1
  5 44  1  0
 44 43  1  0
 42 43  1  6
 42 45  1  0
 45 13  1  0
 13 14  1  1
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 16 40  1  0
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 41 92  1  0
 41 93  1  0
 39 89  1  0
 39 90  1  0
 34 85  1  1
 37 86  1  0
 37 87  1  0
 37 88  1  0
 29 81  1  1
 32 82  1  0
 32 83  1  0
 32 84  1  0
 23 73  1  0
 23 74  1  0
 23 75  1  0
 24 76  1  0
 24 77  1  0
 27 78  1  0
 27 79  1  0
 27 80  1  0
 21 72  1  6
 20 70  1  0
 20 71  1  0
 19 68  1  0
 19 69  1  0
 18 65  1  0
 18 66  1  0
 18 67  1  0
 12 61  1  1
 11 59  1  0
 11 60  1  0
  9 53  1  0
  9 54  1  0
  9 55  1  0
 10 56  1  0
 10 57  1  0
 10 58  1  0
  7 51  1  0
  7 52  1  0
  6 49  1  0
  6 50  1  0
M  END


  Mrv1652309092211262D          

 45 50  0  0  0  0            999 V2000
   -1.2375   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8375   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1377   -1.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2192   -2.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440   -2.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3007   -3.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9327   -3.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -3.7287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 30 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 16 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 13 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
  5 44  1  0  0  0  0
 42 45  1  0  0  0  0
 13 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12CCC34CC3(C=CC3C5(C)CC(OC(C)=O)C(OC(C)=O)C(C)(COC(C)=O)C5CCC43C)C1CC(C)(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C37H54O8/c1-22(38)43-21-33(7)26-10-12-34(8)27(32(26,6)18-25(44-23(2)39)29(33)45-24(3)40)11-13-36-20-37(34,36)17-16-35(30(41)42-9)15-14-31(4,5)19-28(35)36/h11,13,25-29H,10,12,14-21H2,1-9H3

> <INCHI_KEY>
LYRZUWJJCFKJRU-UHFFFAOYSA-N

> <FORMULA>
C37H54O8

> <MOLECULAR_WEIGHT>
626.831

> <EXACT_MASS>
626.381868699

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
70.48205700661013

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0^{1,14}.0^{2,11}.0^{5,10}.0^{15,20}]tricos-12-ene-20-carboxylate

> <JCHEM_LOGP>
5.1438393336666675

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.425446617495468

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
167.3228

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0^{1,14}.0^{2,11}.0^{5,10}.0^{15,20}]tricos-12-ene-20-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      -2.310  -5.541   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.540  -4.207   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -4.207   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.770  -5.541   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.770  -2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.217   0.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.503   1.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.770  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.390  -0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.160  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.700  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.930  -0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.470  -0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.010  -0.206   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.780   1.127   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.010   2.461   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.470   2.461   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.780   3.795   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.780  -1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.320  -1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.090  -2.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.630  -2.874   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.320  -4.207   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.010  -2.874   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.457  -3.400   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.743  -4.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.295  -4.917   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.028  -6.434   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.208  -7.423   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.581  -6.960   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.470  -2.874   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.700  -4.207   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.160  -4.207   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.390  -2.874   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.620  -4.207   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.850  -2.874   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.080  -4.207   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.540  -4.207   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.620  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12   44                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14   42   45                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   40                                                  
CONECT   17   16   18   19   37                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   32   37                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   30   17   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   16   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   13   43   45                                             
CONECT   43   42   44                                                       
CONECT   44   43    5                                                       
CONECT   45   42   13                                                       
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
Methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0,.0,.0,.0,]tricos-12-ene-20-carboxylic acid	Generator

Chemical Formula

C₃₇H₅₄O₈

Average Mass

626.8310 Da

Monoisotopic Mass

626.38187 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C12CCC34CC3(C=CC3C5(C)CC(OC(C)=O)C(OC(C)=O)C(C)(COC(C)=O)C5CCC43C)C1CC(C)(C)CC2

InChI Identifier

InChI=1S/C37H54O8/c1-22(38)43-21-33(7)26-10-12-34(8)27(32(26,6)18-25(44-23(2)39)29(33)45-24(3)40)11-13-36-20-37(34,36)17-16-35(30(41)42-9)15-14-31(4,5)19-28(35)36/h11,13,25-29H,10,12,14-21H2,1-9H3

InChI Key

LYRZUWJJCFKJRU-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
Prunella vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Steroid
Tetracarboxylic acid or derivatives
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

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FoodDB ID

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KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

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Wikipedia Link

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METLIN ID

Not Available

PubChem Compound

73811132

PDB ID

Not Available

ChEBI ID

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Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate (NP0282557)

MOL for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

3D MOL for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

3D SDF for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

3D-SDF for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

PDB for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

3D PDB for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

SMILES for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

INCHI for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

Structure for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)

3D Structure for NP0282557 (methyl 7,8-bis(acetyloxy)-6-[(acetyloxy)methyl]-2,6,10,17,17-pentamethylhexacyclo[12.8.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricos-12-ene-20-carboxylate)