NP-MRD: Showing NP-Card for 1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate (NP0325309)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 05:58:31 UTC

Updated at

2022-09-12 05:58:31 UTC

NP-MRD ID

NP0325309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate

Description

1-Methyl (1R,3R,5S,6R)-8-methyl-6-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]Octan-3-yl (2E)-2-methylbut-2-enedioate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate is found in Schizanthus litoralis. Based on a literature review very few articles have been published on 1-methyl (1R,3R,5S,6R)-8-methyl-6-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]Octan-3-yl (2E)-2-methylbut-2-enedioate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207582D          

 30 32  0  0  1  0            999 V2000
    7.3255   -1.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005   -1.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005   -0.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505   -1.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -0.7926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2374    1.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1758    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5675    2.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574    2.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958    3.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    3.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    4.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    5.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8407    4.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    4.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2207    3.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
 27 29  1  1  0  0  0
 13 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -9.8254   -0.0356    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4469   -0.2821    0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4377    0.4249    0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7590    1.3346    1.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0183    0.1360    0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973    0.9492    1.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7253   -0.8371   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3413   -1.1474   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1063   -2.0957   -1.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904   -0.4774    0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9733   -0.8526   -0.2525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2683    0.2939   -0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047   -0.0268   -1.1222 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9602    0.9640   -0.2269 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3381    0.7597   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2743    1.7319   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    2.8752   -0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7142    1.4918   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2346    0.2926   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6598   -0.0033   -0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6398    0.9163   -0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9674    0.4856   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3078   -0.8290   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3303   -1.7574   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0209   -1.3339   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4887    0.4250    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074   -1.0644    0.8708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2962   -1.2417    1.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5320   -1.2194   -0.4723 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -2.4232   -1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3231   -0.8924    0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9783    0.8914    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2848    0.0547   -0.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449    0.3289    1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3672    1.4967    0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5190    1.7229    1.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5292   -1.3829   -0.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -1.6801   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    1.1938   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831    0.4389   -1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    0.0757   -2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    1.9871   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    2.2990   -0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5175   -0.5119   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3810    1.9387   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7134    1.2378   -0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3383   -1.1612   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779   -2.8105    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2694   -2.0987    0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857    0.9548    1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145    0.5165    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643   -1.6975    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596   -0.6197    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4735   -2.3259    1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242   -2.5899   -2.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428   -2.6680   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -3.2635   -0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 28  1  0
 28 27  1  0
 27 26  1  0
 26 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 14 13  1  0
 13 12  1  0
 13 29  1  0
 29 30  1  0
 12 11  1  0
 29 27  1  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
 11 38  1  6
 28 53  1  0
 28 54  1  0
 27 52  1  1
 26 50  1  0
 26 51  1  0
 14 42  1  6
 18 43  1  0
 19 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 13 41  1  6
 12 39  1  0
 12 40  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
M  END


  Mrv1652309122207582D          

 30 32  0  0  1  0            999 V2000
    7.3255   -1.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005   -1.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005   -0.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630   -0.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505   -1.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -0.7926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2374    1.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1758    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5675    2.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574    2.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958    3.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    3.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    4.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    5.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8407    4.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9024    4.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2207    3.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
 27 29  1  1  0  0  0
 13 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(\C)=C\C(=O)O[C@@H]1C[C@@H]2C[C@@H](OC(=O)\C=C\C3=CC=CC=C3)[C@H](C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C23H27NO6/c1-15(23(27)28-3)11-22(26)29-18-12-17-13-20(19(14-18)24(17)2)30-21(25)10-9-16-7-5-4-6-8-16/h4-11,17-20H,12-14H2,1-3H3/b10-9+,15-11+/t17-,18-,19+,20-/m1/s1

> <INCHI_KEY>
DFGZBHQWARLLMF-QAYISPQJSA-N

> <FORMULA>
C23H27NO6

> <MOLECULAR_WEIGHT>
413.47

> <EXACT_MASS>
413.183837593

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.82247928322623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl (1R,3R,5S,6R)-8-methyl-6-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enedioate

> <JCHEM_LOGP>
3.5514217753333326

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.266072105623556

> <JCHEM_POLAR_SURFACE_AREA>
82.14

> <JCHEM_REFRACTIVITY>
111.72039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl (1R,3R,5S,6R)-8-methyl-6-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enedioate

> <JCHEM_VEBER_RULE>
0

$$$$

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      13.674  -2.813   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.134  -2.813   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.364  -1.480   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.134  -0.146   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.824  -1.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.054  -2.813   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.054  -0.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.514  -0.146   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.744  -1.480   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.744   1.188   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.536   2.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.443   2.626   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.328   4.162   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.059   4.830   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.600   5.029   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.485   6.565   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.758   7.432   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.643   8.968   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.915   9.836   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.303   9.167   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.418   7.632   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.145   6.764   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.831   0.418   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       2.602   1.188   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       1.062   1.188   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   14   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   11                                                       
CONECT   29   27   13   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
1-Methyl (1R,3R,5S,6R)-8-methyl-6-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enedioic acid	Generator

Chemical Formula

C₂₃H₂₇NO₆

Average Mass

413.4700 Da

Monoisotopic Mass

413.18384 Da

IUPAC Name

1-methyl (1R,3R,5S,6R)-8-methyl-6-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enedioate

Traditional Name

1-methyl (1R,3R,5S,6R)-8-methyl-6-{[(2E)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enedioate

CAS Registry Number

Not Available

SMILES

COC(=O)C(\C)=C\C(=O)O[C@@H]1C[C@@H]2C[C@@H](OC(=O)\C=C\C3=CC=CC=C3)[C@H](C1)N2C

InChI Identifier

InChI=1S/C23H27NO6/c1-15(23(27)28-3)11-22(26)29-18-12-17-13-20(19(14-18)24(17)2)30-21(25)10-9-16-7-5-4-6-8-16/h4-11,17-20H,12-14H2,1-3H3/b10-9+,15-11+/t17-,18-,19+,20-/m1/s1

InChI Key

DFGZBHQWARLLMF-QAYISPQJSA-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
Schizanthus litoralis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Tricarboxylic acid or derivatives
Tropane alkaloid
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Piperidine
Benzenoid
N-alkylpyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.55	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	82.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	111.72 m³·mol⁻¹	ChemAxon
Polarizability	43.82 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163188959

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate (NP0325309)

MOL for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

3D MOL for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

3D SDF for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

3D-SDF for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

PDB for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

3D PDB for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

SMILES for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

INCHI for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

Structure for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)

3D Structure for NP0325309 (1-methyl (1r,3r,5s,6r)-8-methyl-6-{[(2e)-3-phenylprop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-3-yl (2e)-2-methylbut-2-enedioate)