NP-MRD: Showing NP-Card for (1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate (NP0323816)

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Record Information

Version

2.0

Created at

2022-09-12 03:29:22 UTC

Updated at

2022-09-12 03:29:22 UTC

NP-MRD ID

NP0323816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate

Description

Guayulin A belongs to the class of organic compounds known as bicyclogermacrane and isolepidozane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the bicyclogermacrane (3,7,11,11-tetramethylbicyclo[8.1.0]Undecane, 9CI) skeleton or the isolepidozane skeleton. (1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate is found in Parthenium argentatum. (1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate was first documented in 2021 (PMID: 33809180). Based on a literature review very few articles have been published on Guayulin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205292D          

 26 28  0  0  1  0            999 V2000
    2.0392   -0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5694    0.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    0.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.7628    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6297    1.5088    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4519    1.5766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9821    2.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344    3.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    3.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8646    3.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424    3.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4274    4.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    4.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7195    4.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671    5.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    5.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0751    5.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043    2.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    2.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789    3.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    1.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439    0.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9217    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925    1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    2.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057    1.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  5  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  5 24  1  6  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -4.8316    0.1742   -1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9931    0.3330   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2831    1.3831   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4813    1.5490    0.8105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2466    0.8959    1.0591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8943   -0.4046    0.3756 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5284   -0.2507    0.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0931   -0.3129   -1.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.5157   -2.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388   -0.1466   -1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3331    0.0651   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684    0.2365   -0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4410    0.1936   -1.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8102    0.3608   -1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5390    0.5764   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8732    0.6220    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5196    0.4551    0.7754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1686   -1.4756    1.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6575   -2.7668    1.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9749   -4.0283    1.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722   -2.9852    0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520   -1.9541   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9895   -0.7978    0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    2.2206    0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    3.3912    1.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7674    2.4427   -0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4045    1.1367   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5798   -0.6005   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2175    0.0172   -2.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    2.1988   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9695    2.0600    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043    0.8428    2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2870   -0.5396   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370   -0.2019   -2.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.1154    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197    0.0270   -2.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3217    0.3234   -2.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6000    0.7084   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4624    0.7943    1.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0215    0.4950    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1082   -1.6613    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -1.0660    2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0307   -4.2051    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7629   -3.7594    2.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710   -4.8613    1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -4.0716    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4266   -2.4853   -0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0938   -1.6917   -1.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1096   -0.9145    0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5763   -0.5296    1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540    4.3252    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022    3.4803    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665    3.1605    2.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    1.7031   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1229    3.4698   -1.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3237    2.4688   -1.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 24  1  0
 24 25  1  0
 24 26  1  0
 23  2  1  0
 17 12  1  0
 24  4  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  1
  5 32  1  1
  6 33  1  6
 18 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
M  END


  Mrv1652309122205292D          

 26 28  0  0  1  0            999 V2000
    2.0392   -0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5694    0.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    0.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.7628    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6297    1.5088    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4519    1.5766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9821    2.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344    3.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    3.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8646    3.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424    3.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4274    4.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    4.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7195    4.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671    5.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    5.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0751    5.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043    2.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    2.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789    3.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    1.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439    0.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9217    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925    1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    2.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057    1.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  5  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  5 24  1  6  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\[C@H]2[C@@H]([C@H](C\C(C)=C/CC1)OC(=O)\C=C\C1=CC=CC=C1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O2/c1-17-9-8-10-18(2)16-21(23-20(15-17)24(23,3)4)26-22(25)14-13-19-11-6-5-7-12-19/h5-7,10-15,20-21,23H,8-9,16H2,1-4H3/b14-13+,17-15-,18-10-/t20-,21-,23-/m0/s1

> <INCHI_KEY>
JYEVPOCBZDNGDL-ISCJZRRASA-N

> <FORMULA>
C24H30O2

> <MOLECULAR_WEIGHT>
350.502

> <EXACT_MASS>
350.224580206

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.09486819218796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4Z,8Z,10S)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
6.186501642333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.817792542450847

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
109.6851

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4Z,8Z,10S)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       3.806  -0.981   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.929   0.285   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.395   0.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.518   1.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.175   2.816   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.710   2.943   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.833   4.209   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.491   5.601   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.026   5.728   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.614   6.867   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.079   6.741   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.798   8.006   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.333   7.880   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.210   9.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.552  10.538   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.017  10.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.140   9.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.368   4.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.903   4.462   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.561   5.854   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.780   3.196   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.122   1.804   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.587   1.677   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.359   2.690   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.123   4.027   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.877   2.430   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    6   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2                                                       
CONECT   24    5    4   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀O₂

Average Mass

350.5020 Da

Monoisotopic Mass

350.22458 Da

IUPAC Name

(1R,2S,4Z,8Z,10S)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,2S,4Z,8Z,10S)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

C\C1=C\[C@H]2[C@@H]([C@H](C\C(C)=C/CC1)OC(=O)\C=C\C1=CC=CC=C1)C2(C)C

InChI Identifier

InChI=1S/C24H30O2/c1-17-9-8-10-18(2)16-21(23-20(15-17)24(23,3)4)26-22(25)14-13-19-11-6-5-7-12-19/h5-7,10-15,20-21,23H,8-9,16H2,1-4H3/b14-13+,17-15-,18-10-/t20-,21-,23-/m0/s1

InChI Key

JYEVPOCBZDNGDL-ISCJZRRASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Parthenium argentatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclogermacrane and isolepidozane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the bicyclogermacrane (3,7,11,11-tetramethylbicyclo[8.1.0]Undecane, 9CI) skeleton or the isolepidozane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Bicyclogermacrane and isolepidozane sesquiterpenoids

Alternative Parents

Substituents

Bicyclogermacrane sesquiterpenoid
Cinnamic acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.19	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.69 m³·mol⁻¹	ChemAxon
Polarizability	41.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00037225

Chemspider ID

4945219

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440988

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rozalen J, Garcia-Martinez MM, Carrion ME, Zalacain A, Lopez-Corcoles H, Carmona M: Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray). Plants (Basel). 2021 Mar 12;10(3). pii: plants10030537. doi: 10.3390/plants10030537. [PubMed:33809180 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate (NP0323816)

MOL for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0323816 ((1r,2s,4z,8z,10s)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2e)-3-phenylprop-2-enoate)