NP-MRD: Showing NP-Card for 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate (NP0219210)

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Record Information

Version

2.0

Created at

2022-09-05 20:07:50 UTC

Updated at

2022-09-05 20:07:50 UTC

NP-MRD ID

NP0219210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate

Description

4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]Tetradecan-6-yl acetate belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety. 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate is found in Clitopilus passeckerianus. Based on a literature review very few articles have been published on 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]Tetradecan-6-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120433D          

 60 62  0  0  0  0            999 V2000
    2.5306    3.4533   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532    2.8526   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    1.3706   -0.8453 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3338    1.2524   -1.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169    1.1686   -1.5041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2081    0.8044   -0.6913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5083    1.7435    0.3012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5923    2.6031    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    3.5801    1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883    2.5388   -0.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.5963   -0.2371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8665   -0.8201   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -1.5977   -1.3496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0664   -1.6441   -2.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -2.9615   -0.7372 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.7117   -2.2091    2.3162 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3294   -0.9122    3.0606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7621   -0.3328    2.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7040   -1.0653    0.9756 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.8709    1.3023    0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2603    4.5056    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    3.8274    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
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M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242120433D          

 60 62  0  0  0  0            999 V2000
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    1.3532    2.8526   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4980    0.5435    2.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7040   -1.0653    0.9756 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8012   -0.7306    0.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8606   -1.3372   -0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6161    0.6942    0.4070 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8709    1.3023    0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201    4.4950   -0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    2.9540   -0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946    3.4146   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009    0.5012   -2.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3380    1.0893   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3741    2.2122   -2.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2973    2.1520   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073    0.5137   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0683    0.9484   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603    4.5056    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    3.8274    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    3.0933    2.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025   -1.8793   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4408   -0.2088   -0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.4076    0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0202   -1.3701   -1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -0.6886   -2.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.3872   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -1.9478   -3.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6064   -3.6631   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5771   -3.3757   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565   -3.8334    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -2.9220   -0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -2.9610    2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -2.5338    2.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0283   -1.2510    4.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -0.3065    3.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -2.0189    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236   -0.8056    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869   -2.3604    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488   -1.4005   -1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -0.7947   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525    1.0924    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9834    1.1268    1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  1  0  0  0
  3  4  1  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  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25  3  1  0  0  0  0
 22 11  1  0  0  0  0
 22 17  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  2 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  6 35  1  6  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 13 42  1  6  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 16 48  1  0  0  0  0
 16 49  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 22 54  1  1  0  0  0
 23 55  1  1  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  1  0  0  0
 26 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@]([H])(C([H])([H])[H])[C@@]23C([H])([H])C([H])([H])C(=O)[C@@]2([H])[C@](C([H])([H])[H])([C@]([H])(C([H])([H])[H])C([H])([H])C3([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]1(C([H])=C([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-7-20(5)12-17(26-15(4)23)21(6)13(2)8-10-22(14(3)19(20)25)11-9-16(24)18(21)22/h7,13-14,17-19,25H,1,8-12H2,2-6H3/t13-,14+,17+,18+,19-,20-,21-,22-/m1/s1

> <INCHI_KEY>
KUBKXMIPSJEXGM-UHFFFAOYSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.05801759450332

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3R,4S,6S,7S,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl acetate

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.415277924333333

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.235285938967923

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.42553079147499

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0500695920543217

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
100.54039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,4S,6S,7S,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    2.5306    3.4533   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532    2.8526   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    1.3706   -0.8453 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3338    1.2524   -1.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169    1.1686   -1.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2081    0.8044   -0.6913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5083    1.7435    0.3012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5923    2.6031    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    3.5801    1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883    2.5388   -0.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.5963   -0.2371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8665   -0.8201   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -1.5977   -1.3496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0664   -1.6441   -2.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -2.9615   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700   -2.8678    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6801   -1.6423    0.8657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7117   -2.2091    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294   -0.9122    3.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7621   -0.3328    2.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980    0.5435    2.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7040   -1.0653    0.9756 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8012   -0.7306    0.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8606   -1.3372   -0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6161    0.6942    0.4070 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8709    1.3023    0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201    4.4950   -0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    2.9540   -0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946    3.4146   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009    0.5012   -2.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3380    1.0893   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3741    2.2122   -2.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2973    2.1520   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073    0.5137   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0683    0.9484   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603    4.5056    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    3.8274    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    3.0933    2.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025   -1.8793   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4408   -0.2088   -0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.4076    0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0202   -1.3701   -1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -0.6886   -2.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.3872   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -1.9478   -3.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6064   -3.6631   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5771   -3.3757   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565   -3.8334    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -2.9220   -0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -2.9610    2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -2.5338    2.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0283   -1.2510    4.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -0.3065    3.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -2.0189    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236   -0.8056    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869   -2.3604    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488   -1.4005   -1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -0.7947   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525    1.0924    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9834    1.1268    1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 17 16  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25  3  1  0
 22 11  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  9 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  6
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  1
 23 55  1  1
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  1
 26 60  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       2.531   3.453  -0.502  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.353   2.853  -0.479  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.276   1.371  -0.845  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.334   1.252  -1.945  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.017   1.169  -1.504  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.208   0.804  -0.691  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.508   1.744   0.301  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.592   2.603   0.309  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.823   3.580   1.432  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.388   2.539  -0.669  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.339  -0.596  -0.237  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.866  -0.820  -0.052  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.992  -1.598  -1.350  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.066  -1.644  -2.389  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.764  -2.962  -0.737  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.570  -2.868   0.003  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.680  -1.642   0.866  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.712  -2.209   2.316  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.329  -0.912   3.061  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.762  -0.333   2.228  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.498   0.544   2.567  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.704  -1.065   0.976  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.801  -0.731   0.588  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.861  -1.337  -0.354  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.616   0.694   0.407  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.871   1.302   0.760  0.00  0.00           O+0
HETATM   27  H   UNK     0       2.620   4.495  -0.249  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.464   2.954  -0.771  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.495   3.415  -0.207  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.001   0.501  -2.722  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.338   1.089  -1.577  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.374   2.212  -2.546  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.297   2.152  -2.021  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.007   0.514  -2.423  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.068   0.948  -1.441  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.260   4.506   1.289  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.904   3.827   1.393  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.659   3.093   2.418  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.103  -1.879  -0.026  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.441  -0.209  -0.745  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.062  -0.408   0.975  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.020  -1.370  -1.799  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.596  -0.689  -2.537  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.843  -2.387  -2.053  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.684  -1.948  -3.385  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.606  -3.663  -1.610  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.577  -3.376  -0.167  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.657  -3.833   0.554  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.341  -2.922  -0.788  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.072  -2.961   2.385  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.721  -2.534   2.559  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.028  -1.251   4.051  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.229  -0.307   3.128  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.292  -2.019   1.264  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.424  -0.806   1.553  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.087  -2.360   0.072  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.549  -1.401  -1.380  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.841  -0.795  -0.196  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.953   1.092   1.205  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.983   1.127   1.734  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4    5   25                                             
CONECT    4    3   30   31   32                                             
CONECT    5    3    6   33   34                                             
CONECT    6    5    7   11   35                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   36   37   38                                             
CONECT   10    8                                                            
CONECT   11    6   12   13   22                                             
CONECT   12   11   39   40   41                                             
CONECT   13   11   14   15   42                                             
CONECT   14   13   43   44   45                                             
CONECT   15   13   16   46   47                                             
CONECT   16   15   17   48   49                                             
CONECT   17   16   18   23   22                                             
CONECT   18   17   19   50   51                                             
CONECT   19   18   20   52   53                                             
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   11   17   54                                             
CONECT   23   17   24   25   55                                             
CONECT   24   23   56   57   58                                             
CONECT   25   23   26    3   59                                             
CONECT   26   25   60                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

RDKit          3D

60 62  0  0  0  0  0  0  0  0999 V2000
    2.5306    3.4533   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532    2.8526   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    1.3706   -0.8453 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3338    1.2524   -1.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169    1.1686   -1.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2081    0.8044   -0.6913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5083    1.7435    0.3012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5923    2.6031    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    3.5801    1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883    2.5388   -0.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.5963   -0.2371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8665   -0.8201   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -1.5977   -1.3496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0664   -1.6441   -2.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -2.9615   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700   -2.8678    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6801   -1.6423    0.8657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7117   -2.2091    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294   -0.9122    3.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7621   -0.3328    2.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980    0.5435    2.5668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7040   -1.0653    0.9756 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8012   -0.7306    0.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8606   -1.3372   -0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6161    0.6942    0.4070 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8709    1.3023    0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201    4.4950   -0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639    2.9540   -0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946    3.4146   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009    0.5012   -2.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3380    1.0893   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3741    2.2122   -2.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2973    2.1520   -2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073    0.5137   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0683    0.9484   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603    4.5056    1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    3.8274    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    3.0933    2.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1025   -1.8793   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4408   -0.2088   -0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.4076    0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0202   -1.3701   -1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -0.6886   -2.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.3872   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -1.9478   -3.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6064   -3.6631   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5771   -3.3757   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565   -3.8334    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -2.9220   -0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -2.9610    2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -2.5338    2.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0283   -1.2510    4.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -0.3065    3.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -2.0189    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236   -0.8056    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869   -2.3604    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488   -1.4005   -1.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -0.7947   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525    1.0924    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9834    1.1268    1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 17 16  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25  3  1  0
 22 11  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
  9 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  6
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  1
 23 55  1  1
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  1
 26 60  1  0
M  END

View in JSmol

Synonyms

Value	Source
4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl acetic acid	Generator
4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

(1R,2R,3R,4S,6S,7S,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl acetate

Traditional Name

(1R,2R,3R,4S,6S,7S,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@]([H])(C([H])([H])[H])[C@@]23C([H])([H])C([H])([H])C(=O)[C@@]2([H])[C@](C([H])([H])[H])([C@]([H])(C([H])([H])[H])C([H])([H])C3([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]1(C([H])=C([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H34O4/c1-7-20(5)12-17(26-15(4)23)21(6)13(2)8-10-22(14(3)19(20)25)11-9-16(24)18(21)22/h7,13-14,17-19,25H,1,8-12H2,2-6H3/t13-,14+,17+,18+,19-,20-,21-,22-/m1/s1

InChI Key

KUBKXMIPSJEXGM-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Clitopilus passeckerianus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Pleuromutilin and derivatives

Alternative Parents

Substituents

Pleuromutilin
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.12	ALOGPS
logP	3.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.43	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.54 m³·mol⁻¹	ChemAxon
Polarizability	40.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

78444187

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72279315

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate (NP0219210)

MOL for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

3D MOL for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

3D SDF for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

3D-SDF for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

PDB for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

3D PDB for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

SMILES for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

INCHI for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

Structure for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)

3D Structure for NP0219210 (4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl acetate)