NP-MRD: Showing NP-Card for (2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione (NP0178797)

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Record Information

Version

2.0

Created at

2022-09-03 16:51:22 UTC

Updated at

2022-09-03 16:51:22 UTC

NP-MRD ID

NP0178797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione

Description

Coruscanone A belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. (2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione was first documented in 2004 (PMID: 15174849). Based on a literature review a small amount of articles have been published on Coruscanone A (PMID: 30076924) (PMID: 21903391) (PMID: 17181171).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.7862   -2.6211   -1.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389   -1.2088   -2.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -0.3582   -0.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365    0.0611   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -0.3513   -0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705    0.0239   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8303    0.8444    1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    1.1775    1.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.6745    1.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960   -0.1585    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9788   -0.4656   -0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    0.0685   -0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119   -0.2794   -1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4210   -1.0256   -2.1896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.3933   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8753    1.0920    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6114    1.9122    1.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    0.9365    0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    1.4693    1.3617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6873   -3.1687   -2.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314   -2.9084   -1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735   -2.9084   -1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280    0.7071    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325   -1.0080   -1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594    1.2678    1.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0985    1.8253    2.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1674    0.9117    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1343   -0.5267   -0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645   -1.1116   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4185    0.3272   -0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1675    1.2715    2.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174    2.5271    2.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3471    2.5929    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  3 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  6  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END


  Mrv1652309032218512D          

 19 20  0  0  0  0            999 V2000
    1.5356   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -2.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -2.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7907   -4.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5607   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454   -2.7666    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  3 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0178797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\C(\C=C\C1=CC=CC=C1)=C1/C(=O)C=C(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-11-10-13(17)15(16(11)18)14(19-2)9-8-12-6-4-3-5-7-12/h3-10H,1-2H3/b9-8+,15-14+

> <INCHI_KEY>
QNDUJCPJQJQOAB-IDRAWEHWSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.285

> <EXACT_MASS>
254.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.806865016749512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-[(2E)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione

> <JCHEM_LOGP>
3.1531041439999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.844278275737166

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
76.87519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-[(2E)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.867  -3.195   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.533  -2.425   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.199  -3.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.468  -3.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.136  -3.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.469  -2.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.469  -0.885   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.199  -4.735   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.445  -5.640   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.910  -5.164   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.969  -7.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.571  -7.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.476  -8.351   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.047  -5.640   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.511  -5.164   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    3   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2850 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

(2E)-2-[(2E)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione

Traditional Name

(2E)-2-[(2E)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione

CAS Registry Number

Not Available

SMILES

CO\C(\C=C\C1=CC=CC=C1)=C1/C(=O)C=C(C)C1=O

InChI Identifier

InChI=1S/C16H14O3/c1-11-10-13(17)15(16(11)18)14(19-2)9-8-12-6-4-3-5-7-12/h3-10H,1-2H3/b9-8+,15-14+

InChI Key

QNDUJCPJQJQOAB-IDRAWEHWSA-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 styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.15	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	27.81 Å³	ChemAxon
Number of Rings	2	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

8159336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9983746

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Khan H, Sabbah DA, Zafar M, Mubarak MS: Molecular modeling studies of coruscanone (A) core nucleus as potential antifungal agents. Life Sci. 2018 Sep 15;209:332-340. doi: 10.1016/j.lfs.2018.07.059. Epub 2018 Aug 1. [PubMed:30076924 ]
Tichotova L, Matousova E, Spulak M, Kunes J, Votruba I, Buchta V, Pour M: Synthesis and biological activity of desmethoxy analogues of coruscanone A. Bioorg Med Chem Lett. 2011 Oct 15;21(20):6062-6. doi: 10.1016/j.bmcl.2011.08.059. Epub 2011 Aug 19. [PubMed:21903391 ]
Babu KS, Li XC, Jacob MR, Zhang Q, Khan SI, Ferreira D, Clark AM: Synthesis, antifungal activity, and structure-activity relationships of coruscanone A analogues. J Med Chem. 2006 Dec 28;49(26):7877-86. doi: 10.1021/jm061123i. [PubMed:17181171 ]
Li XC, Ferreira D, Jacob MR, Zhang Q, Khan SI, ElSohly HN, Nagle DG, Smillie TJ, Khan IA, Walker LA, Clark AM: Antifungal cyclopentenediones from Piper coruscans. J Am Chem Soc. 2004 Jun 9;126(22):6872-3. doi: 10.1021/ja048081c. [PubMed:15174849 ]
LOTUS database [Link]

Showing NP-Card for (2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione (NP0178797)

MOL for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

3D MOL for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

3D SDF for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

3D-SDF for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

PDB for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

3D PDB for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

SMILES for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

INCHI for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

Structure for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)

3D Structure for NP0178797 ((2e)-2-[(2e)-1-methoxy-3-phenylprop-2-en-1-ylidene]-4-methylcyclopent-4-ene-1,3-dione)