NP-MRD: Showing NP-Card for (1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0250203)

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Record Information

Version

2.0

Created at

2022-09-07 12:58:23 UTC

Updated at

2022-09-07 12:58:23 UTC

NP-MRD ID

NP0250203

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

1Beta-P-Coumaroyloxypolygodial belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. (1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Drimys brasiliensis. (1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate was first documented in 2013 (PMID: 23517126). Based on a literature review very few articles have been published on 1Beta-P-Coumaroyloxypolygodial.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214582D          

 29 31  0  0  1  0            999 V2000
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.0471   -2.1077    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300   -1.5863    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -2.3310   -1.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -1.8280    1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3607   -0.5957    1.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517    0.5552    1.1009 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5210    0.3460    0.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063    1.2067    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207    2.2491    1.8735 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.9090    0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895   -0.1563    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -0.4690    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873   -1.6488   -0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2879   -1.9766   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3271   -1.1654   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6560   -1.5103   -0.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0432   -0.0069    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3116    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6329    0.6526   -0.2183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7394    0.0639   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.1117   -0.0238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9599    0.3037   -1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107    1.6843   -0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186    2.5278   -0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026    3.9160    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6425    4.6744    0.2231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9284    2.0701   -0.6032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5702    2.3429   -2.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    3.4144   -2.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6098   -1.3032    1.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8405   -2.8802    1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -2.5692   -0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9400   -3.3674   -1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468   -1.8893   -2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212   -2.5342   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297   -2.2614    0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129   -2.5929    1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029   -0.3136    2.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -0.8619    2.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0386    1.4999    1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751    1.6186    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060   -0.8502   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1572   -2.2745   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5135   -2.8927   -1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4022   -0.9004   -0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8879    0.6291    0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775    1.2311    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815   -0.2788   -2.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0057   -0.6609   -0.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954    0.9221   -1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    0.2283    0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8182   -0.3543   -0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5826    0.2516   -2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3167    2.0255   -0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046    4.2461    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2826    2.7939   -0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    1.6048   -2.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  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
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 21  2  1  0
 18 12  1  0
 27 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  1
 10 41  1  0
 11 42  1  0
 13 43  1  0
 14 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  1
 22 52  1  0
 22 53  1  0
 23 54  1  0
 25 55  1  0
 27 56  1  1
 28 57  1  0
M  END


  Mrv1652309072214582D          

 29 31  0  0  1  0            999 V2000
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0250203

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@@]2(C)[C@H]1CC=C(C=O)[C@@H]2C=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O5/c1-23(2)13-12-21(24(3)19(15-26)17(14-25)7-10-20(23)24)29-22(28)11-6-16-4-8-18(27)9-5-16/h4-9,11,14-15,19-21,27H,10,12-13H2,1-3H3/b11-6+/t19-,20-,21+,24+/m0/s1

> <INCHI_KEY>
OOBNDBQPMFZTTD-TWEQYNAUSA-N

> <FORMULA>
C24H28O5

> <MOLECULAR_WEIGHT>
396.483

> <EXACT_MASS>
396.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.04443251635905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aS,8R,8aS)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
4.032133498333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.004916242896371

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398603428130135

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9735026671239275

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
112.17079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,8R,8aS)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.990   1.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   21                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19    6   20   21   27                                             
CONECT   20   19                                                            
CONECT   21   19    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
1b-p-Coumaroyloxypolygodial	Generator
1Β-p-coumaroyloxypolygodial	Generator

Chemical Formula

C₂₄H₂₈O₅

Average Mass

396.4830 Da

Monoisotopic Mass

396.19367 Da

IUPAC Name

(1R,4aS,8R,8aS)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(1R,4aS,8R,8aS)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@@]2(C)[C@H]1CC=C(C=O)[C@@H]2C=O

InChI Identifier

InChI=1S/C24H28O5/c1-23(2)13-12-21(24(3)19(15-26)17(14-25)7-10-20(23)24)29-22(28)11-6-16-4-8-18(27)9-5-16/h4-9,11,14-15,19-21,27H,10,12-13H2,1-3H3/b11-6+/t19-,20-,21+,24+/m0/s1

InChI Key

OOBNDBQPMFZTTD-TWEQYNAUSA-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
Drimys brasiliensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
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
Organic oxygen compound
Carbonyl group
Aldehyde
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	4.03	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.17 m³·mol⁻¹	ChemAxon
Polarizability	43.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29419708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14241022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Devkota KP, Covell D, Ransom T, McMahon JB, Beutler JA: Growth inhibition of human colon carcinoma cells by sesquiterpenoids and tetralones of Zygogynum calothyrsum. J Nat Prod. 2013 Apr 26;76(4):710-4. doi: 10.1021/np400042q. Epub 2013 Mar 21. [PubMed:23517126 ]
LOTUS database [Link]

Showing NP-Card for (1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0250203)

MOL for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0250203 ((1r,4as,8r,8as)-7,8-diformyl-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)