NP-MRD: Showing NP-Card for (1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate (NP0286541)

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Record Information

Version

2.0

Created at

2022-09-09 15:09:51 UTC

Updated at

2022-09-09 15:09:51 UTC

NP-MRD ID

NP0286541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate

Description

SCHEMBL8925834 belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Based on a literature review very few articles have been published on SCHEMBL8925834.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -4.2285    1.4976    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    0.1322   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955   -0.9662    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254    0.0736   -1.5288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3416   -1.2716   -1.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -1.5066    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191   -0.1713    0.6389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5867   -0.1350    2.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4734    0.8503    0.0573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1726    0.3209   -0.1249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    0.8835    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006    1.9455    1.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773    0.2314    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    0.7509    0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228    0.1779    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8028    0.8558    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0945    0.4087    0.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2862   -0.7596    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2316   -1.4425   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9391   -0.9792   -0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0012    1.1520   -1.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9901    1.3827    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    1.9510   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598    2.1818    0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5872   -1.3983    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7371   -0.5590    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5578   -1.8060   -0.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058    0.1916   -2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   -2.0843   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3972   -1.2110   -2.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652   -1.7085    0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835   -2.3405    0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048   -1.1025    2.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6645   -0.1010    2.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1147    0.7362    2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    1.7885    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.6679   -0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030    1.6667    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6361    1.7855    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9455    0.9518    1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2912   -1.1381   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4074   -2.3578   -1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949   -1.5068   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719    2.1597   -1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029    1.1381   -2.1019 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  1
  7  9  1  0
  9 21  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  2  1  0
 20 15  1  0
 21  4  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  1
 21 44  1  0
 21 45  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END


  Mrv1652309092217092D          

 21 23  0  0  1  0            999 V2000
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6340   -0.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    0.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7774   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4919   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2063   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9208   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9208   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2063   -1.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4919   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    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
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CC[C@@]1(C)[C@H](C2)OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O2/c1-18(2)15-11-12-19(18,3)16(13-15)21-17(20)10-9-14-7-5-4-6-8-14/h4-10,15-16H,11-13H2,1-3H3/b10-9+/t15-,16+,19+/m1/s1

> <INCHI_KEY>
ACTRLDZRLKIJEH-CYIVYTTFSA-N

> <FORMULA>
C19H24O2

> <MOLECULAR_WEIGHT>
284.399

> <EXACT_MASS>
284.177630013

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.86212557705651

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
5.023348602333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.81767839108318

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
84.88200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.389   0.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.864   0.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.389  -0.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.249   1.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.916   1.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.916  -0.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.249  -1.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.249  -2.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.583  -0.529   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.917  -1.299   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.250  -0.529   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.250   1.011   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.584  -1.299   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.918  -0.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.251  -1.299   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.585  -0.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.919  -1.299   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.919  -2.839   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.585  -3.609   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.251  -2.839   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.583   1.011   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₂

Average Mass

284.3990 Da

Monoisotopic Mass

284.17763 Da

IUPAC Name

(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2CC[C@@]1(C)[C@H](C2)OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H24O2/c1-18(2)15-11-12-19(18,3)16(13-15)21-17(20)10-9-14-7-5-4-6-8-14/h4-10,15-16H,11-13H2,1-3H3/b10-9+/t15-,16+,19+/m1/s1

InChI Key

ACTRLDZRLKIJEH-CYIVYTTFSA-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 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
Aromatic monoterpenoid
Bornane monoterpenoid
Norbornane monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
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
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	5.02	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	84.88 m³·mol⁻¹	ChemAxon
Polarizability	32.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

25431299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate (NP0286541)

MOL for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0286541 ((1r,2s,4r)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (2e)-3-phenylprop-2-enoate)