NP-MRD: Showing NP-Card for (2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid (NP0230315)

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Record Information

Version

2.0

Created at

2022-09-06 10:43:34 UTC

Updated at

2022-09-06 10:43:34 UTC

NP-MRD ID

NP0230315

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid

Description

Plakotenin, also known as homo-plakotenin, belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid was first documented in 2010 (PMID: 20517579). Based on a literature review a small amount of articles have been published on Plakotenin (PMID: 23037572) (PMID: 22239598).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062212432D          

 26 28  0  0  1  0            999 V2000
    1.9362    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8092    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5271    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7146    2.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698    3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    4.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 18  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 24  1  1  0  0  0
 20 26  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    0.4162    1.7531   -2.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484    0.5865   -1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2867    0.5435   -0.0643 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6201    1.8375    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0781    2.8311    0.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    2.6414    0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608    4.1109    1.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7758    4.3102    1.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3043    5.0906    1.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3387   -0.3081    0.7398 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5730   -0.5695    0.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -1.5948   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7723   -1.9119   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9069   -1.1558   -1.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8784   -0.1133   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7374    0.1784    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8829   -1.5448    1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3630   -1.9025    1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178   -3.1828    2.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -0.8410    1.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7152   -1.2704    1.0763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9619   -2.6567    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620   -0.2925    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -0.3095   -0.9370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3600    0.4182   -2.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8457   -0.2681   -0.1639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3056    2.3500   -1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    2.5023   -2.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0130    1.4909   -3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    0.7153   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -0.3795   -2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216    2.0777    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370    3.6892    1.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195    2.4203   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123    2.1137    1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795    5.1238    2.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735    0.3252    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927   -2.2205   -1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7647   -2.7505   -2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8160   -1.3902   -2.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989    0.4576   -0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7737    0.9968    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473   -2.3206    1.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244   -2.9817    2.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1615   -3.4639    2.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135   -4.0167    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297   -0.0990    2.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2846   -1.0610    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -2.9464   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8815   -2.6061   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2058   -3.3552    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -0.6990   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5245    0.6769    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2787   -1.3859   -1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8027   -0.0081   -3.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4294    0.1027   -2.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4426    1.4962   -2.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -1.2338   -0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  1
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  9  1  0
  7  8  2  0
  3 26  1  0
 26 24  1  0
 24 25  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 17  2  0
 17 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10  3  1  0
 16 11  1  0
 20 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
 26 58  1  6
 24 54  1  6
 25 55  1  0
 25 56  1  0
 25 57  1  0
 23 52  1  0
 23 53  1  0
 21 48  1  1
 22 49  1  0
 22 50  1  0
 22 51  1  0
 20 47  1  1
 19 44  1  0
 19 45  1  0
 19 46  1  0
 17 43  1  0
 10 37  1  1
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
M  END


  Mrv1652309062212432D          

 26 28  0  0  1  0            999 V2000
    1.9362    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8092    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5271    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7146    2.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698    3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    4.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 18  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 24  1  1  0  0  0
 20 26  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230315

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O2/c1-6-24(14-18(5)23(25)26)20(19-10-8-7-9-11-19)13-16(3)21-15(2)12-17(4)22(21)24/h7-11,13-15,17,20-22H,6,12H2,1-5H3,(H,25,26)/b18-14+/t15-,17-,20+,21+,22-,24+/m1/s1

> <INCHI_KEY>
NZZHSJZMHIQBPW-LUGBEJBBSA-N

> <FORMULA>
C24H32O2

> <MOLECULAR_WEIGHT>
352.518

> <EXACT_MASS>
352.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.47596304544212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-[(1R,3R,3aR,4S,5S,7aR)-4-ethyl-1,3,7-trimethyl-5-phenyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid

> <JCHEM_LOGP>
6.092498247000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.057694285104356

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
108.58389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(1R,3R,3aR,4S,5S,7aR)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.614   3.222   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.131   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.111   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.584   4.937   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.067   5.204   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.574   6.117   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.090   5.849   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       7.047   7.564   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10   26                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   10   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20    3                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Homo-plakotenin	MeSH
Nor-plakotenin	MeSH

Chemical Formula

C₂₄H₃₂O₂

Average Mass

352.5180 Da

Monoisotopic Mass

352.24023 Da

IUPAC Name

(2E)-3-[(1R,3R,3aR,4S,5S,7aR)-4-ethyl-1,3,7-trimethyl-5-phenyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid

Traditional Name

(2E)-3-[(1R,3R,3aR,4S,5S,7aR)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H32O2/c1-6-24(14-18(5)23(25)26)20(19-10-8-7-9-11-19)13-16(3)21-15(2)12-17(4)22(21)24/h7-11,13-15,17,20-22H,6,12H2,1-5H3,(H,25,26)/b18-14+/t15-,17-,20+,21+,22-,24+/m1/s1

InChI Key

NZZHSJZMHIQBPW-LUGBEJBBSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Aromatic monoterpenoid
Bicyclic monoterpenoid
11-noriridane monoterpenoid
Medium-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Monocyclic benzene moiety
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	6.09	ChemAxon
pKa (Strongest Acidic)	5.06	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	4	ChemAxon
Refractivity	108.58 m³·mol⁻¹	ChemAxon
Polarizability	41.48 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

C00049459

Chemspider ID

23339044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21775550

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bourcet E, Kaufmann L, Arzt S, Bihlmeier A, Klopper W, Schepers U, Brase S: The plakotenins: biomimetic Diels-Alder reactions, total synthesis, structural investigations, and chemical biology. Chemistry. 2012 Nov 19;18(47):15004-20. doi: 10.1002/chem.201201585. Epub 2012 Oct 4. [PubMed:23037572 ]
Bihlmeier A, Bourcet E, Arzt S, Muller T, Brase S, Klopper W: Structure revision of plakotenin based on computational investigation of transition states and spectroscopic properties. J Am Chem Soc. 2012 Feb 1;134(4):2154-60. doi: 10.1021/ja2087097. Epub 2012 Jan 19. [PubMed:22239598 ]
Arzt S, Bourcet E, Muller T, Brase S: Enantioselective total synthesis of plakotenin, a cytotoxic metabolite from Plakortis sp. Org Biomol Chem. 2010 Jul 21;8(14):3300-6. doi: 10.1039/c004199h. Epub 2010 Jun 2. [PubMed:20517579 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid (NP0230315)

MOL for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

3D MOL for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

3D SDF for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

3D-SDF for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

PDB for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

3D PDB for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

SMILES for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

INCHI for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

Structure for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)

3D Structure for NP0230315 ((2e)-3-[(1r,3r,3ar,4s,5s,7ar)-4-ethyl-1,3,7-trimethyl-5-phenyl-1,2,3,3a,5,7a-hexahydroinden-4-yl]-2-methylprop-2-enoic acid)