NP-MRD: Showing NP-Card for methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate (NP0208766)

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Record Information

Version

1.0

Created at

2022-09-05 05:53:50 UTC

Updated at

2022-09-05 05:53:51 UTC

NP-MRD ID

NP0208766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate

Description

EUROABIENOL belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate is found in Lycopus europaeus. It was first documented in 2010 (PMID: 20674349). Based on a literature review very few articles have been published on EUROABIENOL.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207532D          

 33 35  0  0  1  0            999 V2000
   -1.3918   -4.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -2.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 33 28  1  1  0  0  0
 14 33  1  0  0  0  0
  5 33  1  0  0  0  0
M  END

     RDKit          3D

 67 69  0  0  0  0  0  0  0  0999 V2000
   -2.9930   -3.3850   -1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4730   -2.1147   -1.5937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1418   -1.2019   -0.8103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680   -1.4837   -0.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5098    0.1351   -0.5025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4470    0.8210    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    0.8047   -1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1212    1.4871   -2.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750    2.0299   -0.7462 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0013    3.2415   -0.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479    4.4742   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4181    5.6924   -0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6134    4.5435    0.0638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1723    0.9687    0.1200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1271    1.5444    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1288    0.3506   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1293    0.7282   -0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9298    1.8317   -1.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3097    0.0314   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -1.1003   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   -1.8449   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9536   -0.8980    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9657   -2.3181   -1.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5199   -1.4692    0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3227   -0.7952    0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084   -1.2905    1.6564 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5835   -2.6551    1.9153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1151   -1.1246    1.1580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0106   -0.8571    2.2052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9536   -1.7446    2.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738   -1.4071    3.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847   -2.8875    2.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -0.1991    0.0030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9667   -3.5699   -1.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383   -4.1524   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2352   -3.3800   -3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340    0.1882    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535    1.2463    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459    1.6518   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6186    0.1354   -2.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    1.5918   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483    0.6862   -2.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1807    2.2690   -2.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616    2.3523   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414    5.8020    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1263    5.5789   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2445    6.5749   -0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438    1.1395    2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975    2.6613    1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846    1.4505    2.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6209    2.1795   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0803    0.3600   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7521   -2.6860    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4966   -1.2299    0.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5502    0.1222    0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6328   -0.7522   -0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8682   -2.9403   -1.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0570   -1.4233   -2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0881   -2.8916   -2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -2.3589    1.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4742   -0.8090    2.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2495   -2.7578    2.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944   -2.1565    0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886   -1.7643    3.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5869   -1.9074    4.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -0.3136    3.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.8049   -0.8671 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  6
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  1  1
 14 33  1  0
 33 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28 26  1  0
 26 27  1  0
 26 25  1  0
 25 24  2  0
 24 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 33  5  1  0
 16 25  1  0
 16 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 12 45  1  0
 12 46  1  0
 12 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 33 67  1  6
 28 63  1  6
 31 64  1  0
 31 65  1  0
 31 66  1  0
 26 61  1  1
 27 62  1  0
 24 60  1  0
 19 52  1  0
 18 51  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
M  END


  Mrv1652309052207532D          

 33 35  0  0  1  0            999 V2000
   -1.3918   -4.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -2.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
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 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
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 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 33 28  1  1  0  0  0
 14 33  1  0  0  0  0
  5 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)CC[C@H](OC(C)=O)[C@@]2(C)[C@H]1[C@H](OC(C)=O)[C@@H](O)C1=CC(=CC(O)=C21)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O8/c1-12(2)15-10-16-19(17(28)11-15)25(6)18(32-13(3)26)8-9-24(5,23(30)31-7)22(25)21(20(16)29)33-14(4)27/h10-12,18,20-22,28-29H,8-9H2,1-7H3/t18-,20-,21+,22-,24+,25+/m0/s1

> <INCHI_KEY>
FEMTVABTBAWCEK-YTBAPPOLSA-N

> <FORMULA>
C25H34O8

> <MOLECULAR_WEIGHT>
462.539

> <EXACT_MASS>
462.225368055

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.16602721041349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,4S,4aS,9S,10S,10aR)-4,10-bis(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate

> <JCHEM_LOGP>
3.014772272

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.529602851272358

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.178689295036715

> <JCHEM_PKA_STRONGEST_BASIC>
-3.512332820665076

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
118.81249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4S,4aS,9S,10S,10aR)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.598  -7.754   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.151  -7.227   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.883  -5.710   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.063  -4.720   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.831  -6.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.874  -1.183   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.104   0.151   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564   0.151   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.874   1.485   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.414  -1.183   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.804  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804  -5.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.184  -7.851   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.104  -7.851   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.874  -9.185   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.414  -9.185   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.104 -10.518   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.104  -5.184   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    7   33                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   16   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   14    5                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₈

Average Mass

462.5390 Da

Monoisotopic Mass

462.22537 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)CC[C@H](OC(C)=O)[C@@]2(C)[C@H]1[C@H](OC(C)=O)[C@@H](O)C1=CC(=CC(O)=C21)C(C)C

InChI Identifier

InChI=1S/C25H34O8/c1-12(2)15-10-16-19(17(28)11-15)25(6)18(32-13(3)26)8-9-24(5,23(30)31-7)22(25)21(20(16)29)33-14(4)27/h10-12,18,20-22,28-29H,8-9H2,1-7H3/t18-,20-,21+,22-,24+,25+/m0/s1

InChI Key

FEMTVABTBAWCEK-YTBAPPOLSA-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
Lycopus europaeus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
Tetralin
Tricarboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25050594

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46933232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Radulovic N, Denic M, Stojanovic-Radic Z: Antimicrobial phenolic abietane diterpene from Lycopus europaeus L. (Lamiaceae). Bioorg Med Chem Lett. 2010 Sep 1;20(17):4988-91. doi: 10.1016/j.bmcl.2010.07.063. Epub 2010 Jul 19. [PubMed:20674349 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate (NP0208766)

MOL for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

3D MOL for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

3D SDF for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

3D-SDF for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

PDB for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

3D PDB for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

SMILES for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

INCHI for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

Structure for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)

3D Structure for NP0208766 (methyl (1r,4s,4as,9s,10s,10ar)-4,10-bis(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate)