NP-MRD: Showing NP-Card for Macrophyllic acid A (NP0025577)

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Record Information

Version

2.0

Created at

2021-06-19 17:39:47 UTC

Updated at

2021-06-29 23:50:37 UTC

NP-MRD ID

NP0025577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macrophyllic acid A

Provided By

JEOL Database JEOL Logo

Description

Macrophyllic acid a is also known as macrophyllate a. Macrophyllic acid A is found in Inula macrophylla. Macrophyllic acid A was first documented in 2001 (PMID: 11325229). Based on a literature review very few articles have been published on Macrophyllic acid a.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306192119393D          

 39 40  0  0  0  0            999 V2000
    2.8252   -2.0344   -2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.9117   -2.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -0.2372   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -0.5745    0.2175 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4725    0.6484    0.9354 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8794    0.2931    2.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.3813    2.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4557    0.0161    4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -0.3837    5.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7671    0.1835    4.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638    1.8038    0.9544 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9996    2.1519   -0.4602 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4355    0.9473   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9300    0.5179   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    1.4394   -2.7189 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0368    0.2856   -3.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2723   -0.6046   -3.6819 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5034   -1.9130   -3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631   -2.0765   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133   -2.9962   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -0.9611    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119   -1.3844    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    0.9775    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898   -0.0525    3.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.7186    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719   -0.0828    5.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5983    1.5523    1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.6925    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484    2.9501   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594    2.5789   -0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    0.2561    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    1.3263   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3365   -0.3566   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563    2.1039   -2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.0372   -3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -0.3017   -3.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.6715   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -1.5402   -4.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.1225   -4.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  3  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
 16 17  1  0  0  0  0
  7  8  1  0  0  0  0
 16 15  1  0  0  0  0
  8 10  1  0  0  0  0
 17  2  1  0  0  0  0
  8  9  2  0  0  0  0
  2  3  2  0  0  0  0
  2  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13 14  1  1  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  6  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
  6 24  1  0  0  0  0
  7 25  1  0  0  0  0
 10 26  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 14 33  1  0  0  0  0
M  END

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    2.8252   -2.0344   -2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.9117   -2.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -0.2372   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -0.5745    0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725    0.6484    0.9354 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8794    0.2931    2.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.3813    2.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4557    0.0161    4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -0.3837    5.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7671    0.1835    4.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638    1.8038    0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996    2.1519   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355    0.9473   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9300    0.5179   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    1.4394   -2.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368    0.2856   -3.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723   -0.6046   -3.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5034   -1.9130   -3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631   -2.0765   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133   -2.9962   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -0.9611    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119   -1.3844    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    0.9775    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898   -0.0525    3.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.7186    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719   -0.0828    5.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5983    1.5523    1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.6925    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484    2.9501   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594    2.5789   -0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    0.2561    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    1.3263   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3365   -0.3566   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563    2.1039   -2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.0372   -3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -0.3017   -3.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.6715   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -1.5402   -4.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.1225   -4.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
  3  4  1  0
  4  5  1  0
  5 11  1  0
 11 12  1  0
 13  3  1  0
  5  6  1  0
  6  7  2  0
 16 17  1  0
  7  8  1  0
 16 15  1  0
  8 10  1  0
 17  2  1  0
  8  9  2  0
  2  3  2  0
  2  1  1  0
 13 15  1  0
 13 14  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 15 34  1  0
 15 35  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END

  Mrv1652306192119393D          

 39 40  0  0  0  0            999 V2000
    2.8252   -2.0344   -2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.9117   -2.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -0.2372   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -0.5745    0.2175 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4725    0.6484    0.9354 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8794    0.2931    2.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.3813    2.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4557    0.0161    4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -0.3837    5.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7671    0.1835    4.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638    1.8038    0.9544 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9996    2.1519   -0.4602 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4355    0.9473   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9300    0.5179   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    1.4394   -2.7189 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0368    0.2856   -3.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2723   -0.6046   -3.6819 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5034   -1.9130   -3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631   -2.0765   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133   -2.9962   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -0.9611    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119   -1.3844    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    0.9775    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898   -0.0525    3.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.7186    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719   -0.0828    5.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5983    1.5523    1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.6925    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484    2.9501   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594    2.5789   -0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    0.2561    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    1.3263   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3365   -0.3566   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563    2.1039   -2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.0372   -3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -0.3017   -3.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.6715   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -1.5402   -4.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.1225   -4.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  3  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
 16 17  1  0  0  0  0
  7  8  1  0  0  0  0
 16 15  1  0  0  0  0
  8 10  1  0  0  0  0
 17  2  1  0  0  0  0
  8  9  2  0  0  0  0
  2  3  2  0  0  0  0
  2  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13 14  1  1  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 23  1  6  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
  6 24  1  0  0  0  0
  7 25  1  0  0  0  0
 10 26  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
 14 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])[C@@]1([H])C([H])([H])C2=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-11-4-3-8-15(2)9-7-12(10-13(11)15)5-6-14(16)17/h5-6,12H,3-4,7-10H2,1-2H3,(H,16,17)/b6-5+/t12-,15-/m1/s1

> <INCHI_KEY>
CFUISBDJXHZKJK-OBLPCYNLSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.77201342709269

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(2R,4aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
3.6584286713333336

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.118152743511829

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.2194

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
macrophyllic acid A

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    2.8252   -2.0344   -2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.9117   -2.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -0.2372   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -0.5745    0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725    0.6484    0.9354 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8794    0.2931    2.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.3813    2.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4557    0.0161    4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -0.3837    5.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7671    0.1835    4.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638    1.8038    0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996    2.1519   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355    0.9473   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9300    0.5179   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    1.4394   -2.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368    0.2856   -3.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723   -0.6046   -3.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5034   -1.9130   -3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631   -2.0765   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133   -2.9962   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -0.9611    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119   -1.3844    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    0.9775    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898   -0.0525    3.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.7186    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719   -0.0828    5.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5983    1.5523    1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.6925    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484    2.9501   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594    2.5789   -0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    0.2561    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    1.3263   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3365   -0.3566   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563    2.1039   -2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.0372   -3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -0.3017   -3.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.6715   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -1.5402   -4.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.1225   -4.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
  3  4  1  0
  4  5  1  0
  5 11  1  0
 11 12  1  0
 13  3  1  0
  5  6  1  0
  6  7  2  0
 16 17  1  0
  7  8  1  0
 16 15  1  0
  8 10  1  0
 17  2  1  0
  8  9  2  0
  2  3  2  0
  2  1  1  0
 13 15  1  0
 13 14  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 15 34  1  0
 15 35  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       2.825  -2.034  -2.323  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.817  -0.912  -2.301  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.419  -0.237  -1.194  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.879  -0.575   0.218  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.473   0.648   0.935  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.879   0.293   2.346  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.139   0.381   2.802  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.456   0.016   4.189  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.690  -0.384   5.045  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.767   0.184   4.421  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.464   1.804   0.954  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.000   2.152  -0.460  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.436   0.947  -1.262  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.930   0.518  -0.676  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.215   1.439  -2.719  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.037   0.286  -3.692  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.272  -0.605  -3.682  0.00  0.00           C+0
HETATM   18  H   UNK     0       3.503  -1.913  -3.176  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.463  -2.076  -1.439  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.313  -2.996  -2.429  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.019  -0.961   0.780  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.612  -1.384   0.238  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.359   0.978   0.375  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.090  -0.053   3.014  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.959   0.719   2.179  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.872  -0.083   5.358  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.598   1.552   1.580  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.922   2.692   1.407  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.248   2.950  -0.403  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.859   2.579  -0.995  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.869   0.256   0.384  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.665   1.326  -0.763  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.337  -0.357  -1.196  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.656   2.104  -2.772  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.075   2.037  -3.053  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.852  -0.302  -3.433  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.129   0.672  -4.704  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.022  -1.540  -4.197  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.068  -0.123  -4.264  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2   17    3    1                                                  
CONECT    3    4   13    2                                                  
CONECT    4    3    5   21   22                                             
CONECT    5    4   11    6   23                                             
CONECT    6    5    7   24                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   26                                                       
CONECT   11    5   12   27   28                                             
CONECT   12   13   11   29   30                                             
CONECT   13   12    3   15   14                                             
CONECT   14   13   31   32   33                                             
CONECT   15   16   13   34   35                                             
CONECT   16   17   15   36   37                                             
CONECT   17   16    2   38   39                                             
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    4                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    6                                                            
CONECT   25    7                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   12                                                            
CONECT   31   14                                                            
CONECT   32   14                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
    2.8252   -2.0344   -2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.9117   -2.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -0.2372   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -0.5745    0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725    0.6484    0.9354 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8794    0.2931    2.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.3813    2.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4557    0.0161    4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -0.3837    5.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7671    0.1835    4.4212 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638    1.8038    0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996    2.1519   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355    0.9473   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9300    0.5179   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    1.4394   -2.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368    0.2856   -3.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723   -0.6046   -3.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5034   -1.9130   -3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631   -2.0765   -1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3133   -2.9962   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -0.9611    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119   -1.3844    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    0.9775    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898   -0.0525    3.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586    0.7186    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719   -0.0828    5.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5983    1.5523    1.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.6925    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484    2.9501   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594    2.5789   -0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    0.2561    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    1.3263   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3365   -0.3566   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563    2.1039   -2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    2.0372   -3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -0.3017   -3.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.6715   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -1.5402   -4.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.1225   -4.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
  3  4  1  0
  4  5  1  0
  5 11  1  0
 11 12  1  0
 13  3  1  0
  5  6  1  0
  6  7  2  0
 16 17  1  0
  7  8  1  0
 16 15  1  0
  8 10  1  0
 17  2  1  0
  8  9  2  0
  2  3  2  0
  2  1  1  0
 13 15  1  0
 13 14  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 15 34  1  0
 15 35  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Macrophyllate a	Generator

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

(2E)-3-[(2R,4aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]prop-2-enoic acid

Traditional Name

macrophyllic acid A

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(/[H])[C@@]1([H])C([H])([H])C2=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C15H22O2/c1-11-4-3-8-15(2)9-7-12(10-13(11)15)5-6-14(16)17/h5-6,12H,3-4,7-10H2,1-2H3,(H,16,17)/b6-5+/t12-,15-/m1/s1

InChI Key

CFUISBDJXHZKJK-OBLPCYNLSA-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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Inula macrophylla	JEOL database	Su, B.-N., et al, J. Nat. Prod. 64, 466 (2001)

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	3.98	ALOGPS
logP	3.66	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.22 m³·mol⁻¹	ChemAxon
Polarizability	27.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00046102

Chemspider ID

10214215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Su BN, Takaishi Y, Yabuuchi T, Kusumi T, Tori M, Takaoka S, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O: Sesquiterpenes and monoterpenes from the bark of Inula macrophylla. J Nat Prod. 2001 Apr;64(4):466-71. doi: 10.1021/np000211h. [PubMed:11325229 ]
Su, B.-N., et al. (2001). Su, B.-N., et al, J. Nat. Prod. 64, 466 (2001). J. Nat. Prod..

Showing NP-Card for Macrophyllic acid A (NP0025577)

MOL for NP0025577 (Macrophyllic acid A)

3D MOL for NP0025577 (Macrophyllic acid A)

3D SDF for NP0025577 (Macrophyllic acid A)

3D-SDF for NP0025577 (Macrophyllic acid A)

PDB for NP0025577 (Macrophyllic acid A)

3D PDB for NP0025577 (Macrophyllic acid A)

SMILES for NP0025577 (Macrophyllic acid A)

INCHI for NP0025577 (Macrophyllic acid A)

Structure for NP0025577 (Macrophyllic acid A)

3D Structure for NP0025577 (Macrophyllic acid A)