NP-MRD: Showing NP-Card for parnapimarol (NP0033801)

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Record Information

Version

2.0

Created at

2021-06-20 17:42:58 UTC

Updated at

2021-06-30 00:03:48 UTC

NP-MRD ID

NP0033801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

parnapimarol

Provided By

JEOL Database JEOL Logo

Description

parnapimarol is found in Nepeta parnassica. parnapimarol was first documented in 2008 (Gkinis, G., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119423D          

 74 76  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 74 76  0  0  0  0  0  0  0  0999 V2000
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 15 52  1  0
 20 60  1  0
 20 61  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
 24 62  1  1
 26 66  1  0
 26 67  1  0
 19 57  1  0
 19 58  1  0
 19 59  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
  2 35  1  0
  1 33  1  0
  1 34  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END


  Mrv1652306202119423D          

 74 76  0  0  0  0            999 V2000
   -5.5191    1.7334   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303    0.8300   -1.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.6891   -0.9750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4631   -0.7077   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.7815    0.1156 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0760    1.6285    1.0559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7695    1.2416    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407    0.8693   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307    0.5049   -1.6493 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8247    0.6871   -0.8574 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6107    0.3563    0.6281 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5246    1.3194    1.2486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9170    2.8186    1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.8872    2.7335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3061   -0.4143    2.7864 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    0.8410    3.5409 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6096   -0.1220    2.9316 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9480    0.1633    1.4436 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9241    1.3550    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488   -1.0699    0.9057 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9129   -2.2336    0.8667 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052   -3.3588    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.4283    0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314   -4.5248    0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3626   -4.4085    1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0807   -4.7558   -1.1289 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2393   -3.6338   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9895    0.7657   -1.7855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9707    1.9609   -2.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    1.7982   -3.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    3.1322   -4.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834    0.7357   -4.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5743    2.5048   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3144    1.7158   -2.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5692    0.0978   -2.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.9659    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5381   -1.4955   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3648   -0.7635    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2241    2.7746   -0.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    1.7728    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9574    2.5750    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3273    0.8722    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    1.0840   -2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.5494   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898    1.7118   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844    0.0411   -1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359   -0.6382    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    3.0508    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    3.4451    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012    3.1822    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.5789    3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -0.6266    3.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735    0.4965    4.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0269    1.8403    3.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129   -1.1404    3.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5257   -0.0996    3.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8977    1.0887    1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091    1.6548    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    2.2295    1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387   -0.8711   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.2753    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -5.4040    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7311   -4.3061    2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7306   -3.5384    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -5.3025    1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -4.8953   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079   -5.6897   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024   -3.4967   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9832   -3.8705   -2.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -2.6854   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -0.1389   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647    3.7695   -4.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990    3.5989   -4.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    2.9960   -5.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
 12  7  1  0  0  0  0
 18 20  1  6  0  0  0
 11 10  1  0  0  0  0
  3  4  1  0  0  0  0
 10  9  1  0  0  0  0
 20 21  1  0  0  0  0
  9  8  1  0  0  0  0
 21 22  1  0  0  0  0
  7  8  2  0  0  0  0
 22 24  1  0  0  0  0
 18 11  1  0  0  0  0
 24 26  1  0  0  0  0
 12 14  1  0  0  0  0
 18 19  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  1  0  0  0
 28 29  1  0  0  0  0
 16 17  1  0  0  0  0
  3  2  1  6  0  0  0
 16 14  1  0  0  0  0
  2  1  2  3  0  0  0
  7  6  1  0  0  0  0
 22 23  2  0  0  0  0
  8 28  1  0  0  0  0
 24 25  1  0  0  0  0
 28  3  1  0  0  0  0
 26 27  1  0  0  0  0
  3  5  1  0  0  0  0
 29 30  1  0  0  0  0
  5  6  1  0  0  0  0
 30 31  1  0  0  0  0
 17 18  1  0  0  0  0
 30 32  2  0  0  0  0
 16 53  1  0  0  0  0
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 17 56  1  0  0  0  0
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 11 47  1  6  0  0  0
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 10 46  1  0  0  0  0
  9 43  1  0  0  0  0
  9 44  1  0  0  0  0
 28 71  1  6  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
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 15 52  1  0  0  0  0
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  4 36  1  0  0  0  0
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  4 38  1  0  0  0  0
 24 62  1  1  0  0  0
 26 66  1  0  0  0  0
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 13 48  1  0  0  0  0
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  2 35  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 25 65  1  0  0  0  0
 27 68  1  0  0  0  0
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 27 70  1  0  0  0  0
 31 72  1  0  0  0  0
 31 73  1  0  0  0  0
 31 74  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])(C([H])([H])OC(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])C3=C(C([H])([H])C([H])([H])[C@](C([H])=C([H])[H])(C([H])([H])[H])[C@@]3([H])OC(=O)C([H])([H])[H])[C@@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O5/c1-8-17(3)24(30)31-16-26(6)15-13-22(29)27(7)20-12-14-25(5,9-2)23(32-18(4)28)19(20)10-11-21(26)27/h9,17,21-23,29H,2,8,10-16H2,1,3-7H3/t17-,21-,22-,23-,25+,26-,27+/m0/s1

> <INCHI_KEY>
QKFZOHYVWBVZEU-CENPHFALSA-N

> <FORMULA>
C27H42O5

> <MOLECULAR_WEIGHT>
446.628

> <EXACT_MASS>
446.303224452

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.928185420352605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,4S,4aS,7S,8R,10aS)-8-(acetyloxy)-7-ethenyl-4-hydroxy-1,4a,7-trimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthren-1-yl]methyl (2S)-2-methylbutanoate

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
4.815689935666667

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5943265156062022

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
125.1081

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4S,4aS,7S,8R,10aS)-8-(acetyloxy)-7-ethenyl-4-hydroxy-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthren-1-yl]methyl (2S)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 74 76  0  0  0  0  0  0  0  0999 V2000
   -5.5191    1.7334   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303    0.8300   -1.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.6891   -0.9750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4631   -0.7077   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.7815    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760    1.6285    1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695    1.2416    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407    0.8693   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307    0.5049   -1.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247    0.6871   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107    0.3563    0.6281 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5246    1.3194    1.2486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9170    2.8186    1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.8872    2.7335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3061   -0.4143    2.7864 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    0.8410    3.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -0.1220    2.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480    0.1633    1.4436 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9241    1.3550    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488   -1.0699    0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5052   -3.3588    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.4283    0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314   -4.5248    0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3626   -4.4085    1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0807   -4.7558   -1.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -3.6338   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9895    0.7657   -1.7855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9707    1.9609   -2.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    1.7982   -3.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    3.1322   -4.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834    0.7357   -4.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6104   -0.9659    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5381   -1.4955   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2241    2.7746   -0.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    1.7728    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3273    0.8722    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    1.0840   -2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.5494   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898    1.7118   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844    0.0411   -1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359   -0.6382    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    3.0508    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    3.4451    1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012    3.1822    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.5789    3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691   -0.6266    3.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735    0.4965    4.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0269    1.8403    3.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129   -1.1404    3.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5257   -0.0996    3.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8977    1.0887    1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091    1.6548    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    2.2295    1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387   -0.8711   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.2753    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -5.4040    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7311   -4.3061    2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7306   -3.5384    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -5.3025    1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -4.8953   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079   -5.6897   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024   -3.4967   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9832   -3.8705   -2.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -2.6854   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -0.1389   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647    3.7695   -4.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990    3.5989   -4.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    2.9960   -5.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 12  7  1  0
 18 20  1  6
 11 10  1  0
  3  4  1  0
 10  9  1  0
 20 21  1  0
  9  8  1  0
 21 22  1  0
  7  8  2  0
 22 24  1  0
 18 11  1  0
 24 26  1  0
 12 14  1  0
 18 19  1  0
 12 11  1  0
 12 13  1  1
 28 29  1  0
 16 17  1  0
  3  2  1  6
 16 14  1  0
  2  1  2  3
  7  6  1  0
 22 23  2  0
  8 28  1  0
 24 25  1  0
 28  3  1  0
 26 27  1  0
  3  5  1  0
 29 30  1  0
  5  6  1  0
 30 31  1  0
 17 18  1  0
 30 32  2  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 14 51  1  1
 11 47  1  6
 10 45  1  0
 10 46  1  0
  9 43  1  0
  9 44  1  0
 28 71  1  6
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
 15 52  1  0
 20 60  1  0
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 27 68  1  0
 27 69  1  0
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 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.519   1.733  -1.864  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.530   0.830  -1.915  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.326   0.689  -0.975  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.463  -0.708  -0.321  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.276   1.782   0.116  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.076   1.629   1.056  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770   1.242   0.384  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.741   0.869  -0.918  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.531   0.505  -1.649  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.825   0.687  -0.857  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.611   0.356   0.628  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.525   1.319   1.249  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.917   2.819   1.218  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.292   0.887   2.733  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.306  -0.414   2.786  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.593   0.841   3.541  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.610  -0.122   2.932  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.948   0.163   1.444  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.924   1.355   1.355  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.749  -1.070   0.906  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.913  -2.234   0.867  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.505  -3.359   0.392  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.670  -3.428   0.018  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.531  -4.525   0.321  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.363  -4.409   1.300  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.081  -4.756  -1.129  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.239  -3.634  -1.724  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.990   0.766  -1.786  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.971   1.961  -2.601  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.196   1.798  -3.930  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.180   3.132  -4.611  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.383   0.736  -4.506  0.00  0.00           O+0
HETATM   33  H   UNK     0      -5.574   2.505  -1.105  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.314   1.716  -2.604  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.569   0.098  -2.725  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.610  -0.966   0.314  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.538  -1.496  -1.081  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.365  -0.764   0.300  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.224   2.775  -0.352  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.191   1.773   0.721  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.957   2.575   1.595  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.327   0.872   1.808  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.610   1.084  -2.577  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.454  -0.549  -1.944  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.190   1.712  -0.983  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.584   0.041  -1.308  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.136  -0.638   0.635  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.796   3.051   1.814  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.117   3.445   1.631  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.101   3.182   0.202  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.400   1.579   3.228  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.469  -0.627   3.721  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.373   0.497   4.559  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.027   1.840   3.642  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.213  -1.140   3.035  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.526  -0.100   3.536  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.898   1.089   1.786  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.109   1.655   0.319  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.590   2.229   1.911  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.139  -0.871  -0.099  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.603  -1.275   1.565  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.109  -5.404   0.638  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.731  -4.306   2.326  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.731  -3.538   1.095  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.732  -5.303   1.256  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.965  -4.895  -1.764  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.508  -5.690  -1.182  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.302  -3.497  -1.176  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.983  -3.870  -2.761  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.784  -2.685  -1.725  0.00  0.00           H+0
HETATM   71  H   UNK     0      -1.902  -0.139  -2.403  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.965   3.769  -4.197  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.199   3.599  -4.488  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.370   2.996  -5.680  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    3    1   35                                                  
CONECT    3    4    2   28    5                                             
CONECT    4    3   36   37   38                                             
CONECT    5    3    6   39   40                                             
CONECT    6    7    5   41   42                                             
CONECT    7   12    8    6                                                  
CONECT    8    9    7   28                                                  
CONECT    9   10    8   43   44                                             
CONECT   10   11    9   45   46                                             
CONECT   11   10   18   12   47                                             
CONECT   12    7   14   11   13                                             
CONECT   13   12   48   49   50                                             
CONECT   14   15   12   16   51                                             
CONECT   15   14   52                                                       
CONECT   16   17   14   53   54                                             
CONECT   17   16   18   55   56                                             
CONECT   18   20   11   19   17                                             
CONECT   19   18   57   58   59                                             
CONECT   20   18   21   60   61                                             
CONECT   21   20   22                                                       
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   26   25   62                                             
CONECT   25   24   63   64   65                                             
CONECT   26   24   27   66   67                                             
CONECT   27   26   68   69   70                                             
CONECT   28   29    8    3   71                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   72   73   74                                             
CONECT   32   30                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    9                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   13                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   17                                                            
CONECT   56   17                                                            
CONECT   57   19                                                            
CONECT   58   19                                                            
CONECT   59   19                                                            
CONECT   60   20                                                            
CONECT   61   20                                                            
CONECT   62   24                                                            
CONECT   63   25                                                            
CONECT   64   25                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   26                                                            
CONECT   68   27                                                            
CONECT   69   27                                                            
CONECT   70   27                                                            
CONECT   71   28                                                            
CONECT   72   31                                                            
CONECT   73   31                                                            
CONECT   74   31                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  152    0
END

RDKit          3D

74 76  0  0  0  0  0  0  0  0999 V2000
   -5.5191    1.7334   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303    0.8300   -1.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    0.6891   -0.9750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4631   -0.7077   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.7815    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760    1.6285    1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695    1.2416    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407    0.8693   -0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307    0.5049   -1.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247    0.6871   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107    0.3563    0.6281 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5246    1.3194    1.2486 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9170    2.8186    1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.8872    2.7335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3061   -0.4143    2.7864 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6096   -0.1220    2.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6695   -3.4283    0.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3626   -4.4085    1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0807   -4.7558   -1.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -3.6338   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9895    0.7657   -1.7855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9707    1.9609   -2.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1962    1.7982   -3.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    3.1322   -4.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834    0.7357   -4.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5743    2.5048   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3144    1.7158   -2.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5692    0.0978   -2.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.9659    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5381   -1.4955   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3648   -0.7635    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2241    2.7746   -0.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913    1.7728    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9574    2.5750    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3273    0.8722    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    1.0840   -2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.5494   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5844    0.0411   -1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359   -0.6382    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    3.0508    1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8977    1.0887    1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5903    2.2295    1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387   -0.8711   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.2753    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -5.4040    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7311   -4.3061    2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7306   -3.5384    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -5.3025    1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -4.8953   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079   -5.6897   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024   -3.4967   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9832   -3.8705   -2.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -2.6854   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -0.1389   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647    3.7695   -4.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990    3.5989   -4.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    2.9960   -5.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 12  7  1  0
 18 20  1  6
 11 10  1  0
  3  4  1  0
 10  9  1  0
 20 21  1  0
  9  8  1  0
 21 22  1  0
  7  8  2  0
 22 24  1  0
 18 11  1  0
 24 26  1  0
 12 14  1  0
 18 19  1  0
 12 11  1  0
 12 13  1  1
 28 29  1  0
 16 17  1  0
  3  2  1  6
 16 14  1  0
  2  1  2  3
  7  6  1  0
 22 23  2  0
  8 28  1  0
 24 25  1  0
 28  3  1  0
 26 27  1  0
  3  5  1  0
 29 30  1  0
  5  6  1  0
 30 31  1  0
 17 18  1  0
 30 32  2  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 14 51  1  1
 11 47  1  6
 10 45  1  0
 10 46  1  0
  9 43  1  0
  9 44  1  0
 28 71  1  6
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
 15 52  1  0
 20 60  1  0
 20 61  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
 24 62  1  1
 26 66  1  0
 26 67  1  0
 19 57  1  0
 19 58  1  0
 19 59  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
  2 35  1  0
  1 33  1  0
  1 34  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₅

Average Mass

446.6280 Da

Monoisotopic Mass

446.30322 Da

IUPAC Name

[(1R,4S,4aS,7S,8R,10aS)-8-(acetyloxy)-7-ethenyl-4-hydroxy-1,4a,7-trimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthren-1-yl]methyl (2S)-2-methylbutanoate

Traditional Name

[(1R,4S,4aS,7S,8R,10aS)-8-(acetyloxy)-7-ethenyl-4-hydroxy-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthren-1-yl]methyl (2S)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])(C([H])([H])OC(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])C3=C(C([H])([H])C([H])([H])[C@](C([H])=C([H])[H])(C([H])([H])[H])[C@@]3([H])OC(=O)C([H])([H])[H])[C@@]12C([H])([H])[H]

InChI Identifier

InChI=1S/C27H42O5/c1-8-17(3)24(30)31-16-26(6)15-13-22(29)27(7)20-12-14-25(5,9-2)23(32-18(4)28)19(20)10-11-21(26)27/h9,17,21-23,29H,2,8,10-16H2,1,3-7H3/t17-,21-,22-,23-,25+,26-,27+/m0/s1

InChI Key

QKFZOHYVWBVZEU-CENPHFALSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nepeta parnassica	JEOL database	Gkinis, G., et al, J. Nat. Prod. 71, 926 (2008)

Chemical Taxonomy

Classification

Not classified

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	5.15	ALOGPS
logP	4.82	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	-0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	125.11 m³·mol⁻¹	ChemAxon
Polarizability	50.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Gkinis, G., et al. (2008). Gkinis, G., et al, J. Nat. Prod. 71, 926 (2008) . J. Nat. Prod..

Showing NP-Card for parnapimarol (NP0033801)

MOL for NP0033801 (parnapimarol)

3D MOL for NP0033801 (parnapimarol)

3D SDF for NP0033801 (parnapimarol)

3D-SDF for NP0033801 (parnapimarol)

PDB for NP0033801 (parnapimarol)

3D PDB for NP0033801 (parnapimarol)

SMILES for NP0033801 (parnapimarol)

INCHI for NP0033801 (parnapimarol)

Structure for NP0033801 (parnapimarol)

3D Structure for NP0033801 (parnapimarol)