NP-MRD: Showing NP-Card for methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate (NP0243811)

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Record Information

Version

2.0

Created at

2022-09-07 04:26:38 UTC

Updated at

2022-09-07 04:26:39 UTC

NP-MRD ID

NP0243811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate

Description

MEGxp0_001535 belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate is found in Werneria nubigena. Based on a literature review very few articles have been published on MEGxp0_001535.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
    7.7605    1.2364   -1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6501    0.7413   -0.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516    0.9036   -0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0684    1.5234   -2.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179    0.3748   -0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9815    0.5344   -0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8384    0.0442    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9746   -0.6623    1.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8602   -1.1073    1.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -0.8532    1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4953   -1.3300    2.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -2.0398    3.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.1611    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892    0.1281   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0681   -0.1864    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394    0.1692   -0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8360    1.4555    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4008   -0.8729   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    0.4308   -1.8854 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686    0.2786   -0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2641    2.0772   -0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864    1.5655   -2.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5137    0.4163   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4751   -0.1461    0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8314    1.0894   -1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -0.8476    1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -1.6657    2.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9033   -1.3833    4.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6192   -2.9048    3.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2960   -2.4550    3.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851    0.7036   -1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666   -0.7370    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6148    1.3838    1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9060    1.5433   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    2.3396   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4023   -1.3894    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3922   -0.3364   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3977   -1.6164   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8773    0.9183   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    0.8375   -1.2806 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 13 20  2  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END


  Mrv1652309072206262D          

 20 20  0  0  0  0            999 V2000
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  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    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  0  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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    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
   -0.7145   -0.4125    0.0000 C   0  0  0  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
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 13 20  2  0  0  0  0
  7 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1=CC=C(OC)C(\C=C\C(C)(C)O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O4/c1-16(2,18)10-9-13-11-12(5-7-14(13)19-3)6-8-15(17)20-4/h5-11,18H,1-4H3/b8-6+,10-9+

> <INCHI_KEY>
FMRWLSIFAAUVQU-QGHYKFKQSA-N

> <FORMULA>
C16H20O4

> <MOLECULAR_WEIGHT>
276.332

> <EXACT_MASS>
276.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.959325662930915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-{3-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate

> <JCHEM_LOGP>
2.8973599826666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.010609513611431

> <JCHEM_PKA_STRONGEST_BASIC>
-2.79415939874636

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
80.48370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-{3-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}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       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.771   0.564   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.231  -2.104   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   1.540   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   13    7                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₄

Average Mass

276.3320 Da

Monoisotopic Mass

276.13616 Da

IUPAC Name

methyl (2E)-3-{3-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate

Traditional Name

methyl (2E)-3-{3-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C1=CC=C(OC)C(\C=C\C(C)(C)O)=C1

InChI Identifier

InChI=1S/C16H20O4/c1-16(2,18)10-9-13-11-12(5-7-14(13)19-3)6-8-15(17)20-4/h5-11,18H,1-4H3/b8-6+,10-9+

InChI Key

FMRWLSIFAAUVQU-QGHYKFKQSA-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
Werneria nubigena	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
Cinnamyl alcohol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.9	ChemAxon
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.48 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

22913755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23955901

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate (NP0243811)

MOL for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

3D MOL for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

3D SDF for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

3D-SDF for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

PDB for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

3D PDB for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

SMILES for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

INCHI for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

Structure for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)

3D Structure for NP0243811 (methyl (2e)-3-{3-[(1e)-3-hydroxy-3-methylbut-1-en-1-yl]-4-methoxyphenyl}prop-2-enoate)