NP-MRD: Showing NP-Card for Encecalin (NP0051415)

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Record Information

Version

2.0

Created at

2022-04-27 22:47:29 UTC

Updated at

2022-04-27 22:47:29 UTC

NP-MRD ID

NP0051415

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Encecalin

Description

1-(7-Methoxy-2,2-dimethyl-2H-chromen-6-yl)ethan-1-one belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Encecalin is found in Eupatorium glandulosum, Ageratina conyzoides, Ageratina glechonophylla, Ageratina pichinchensis var. bustamenta, Ageratina scorodonoides, Ageratum conyzoides, Anthemis cotula, Baccharis salicifolia, Brasilia sickii, Encelia californica, Encelia canescens, Encelia farinosa, Ageratina altissima, Flourensia riparia, Flourensia riparia Grisebach, Flourensia thurifera, Helianthella quinquenervis, Helianthus hirsutus, Hemizonia congesta, Hemizonia fitchii, Lagascea rigida and Tithonia diversifolia. 1-(7-Methoxy-2,2-dimethyl-2H-chromen-6-yl)ethan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
    2.9006    3.0851   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612    1.6809    0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456    0.8644    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    1.3468    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242    0.4733    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -0.8862    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -1.3678    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520   -0.5160    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872   -1.0679    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6941   -2.5102    0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4704   -0.2953    0.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893   -1.7381    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6350   -1.2872    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8828    0.1621    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756    0.4040   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7492    0.5497    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254    0.9320    0.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    3.5782   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190    3.3144   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    3.4589    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733    2.4030   -0.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353   -2.4344    0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -2.8508    1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7602   -2.7701    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0783   -3.0963   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207   -2.8067    0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4573   -1.9882    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7634    0.4796   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5168   -0.4129   -1.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3945    1.3506   -1.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1710    1.2664    1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870   -0.3112    1.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7062    0.9895    0.9561 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
  4  5  1  0
  5  6  2  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  8  3  1  0
 17  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
  7 22  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
M  END


  Mrv1533004231522212D          

 17 18  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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  0  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   -1.2375    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=CC(C)(C)O2)C=C1C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c1-9(15)11-7-10-5-6-14(2,3)17-12(10)8-13(11)16-4/h5-8H,1-4H3

> <INCHI_KEY>
WXVLCNREBFDEKS-UHFFFAOYSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.279

> <EXACT_MASS>
232.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.520964699559546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethan-1-one

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.2738454710000005

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.763881273419251

> <JCHEM_PKA_STRONGEST_BASIC>
-4.602238180412138

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
67.3174

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
encecalin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.195   0.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.185  -1.037   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
1-(7-Methoxy-2,2-dimethyl-2H-1-benzopyran-6-yl)ethanone	Kegg

Chemical Formula

C₁₄H₁₆O₃

Average Mass

232.2790 Da

Monoisotopic Mass

232.10994 Da

IUPAC Name

1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethan-1-one

Traditional Name

encecalin

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=CC(C)(C)O2)C=C1C(C)=O

InChI Identifier

InChI=1S/C14H16O3/c1-9(15)11-7-10-5-6-14(2,3)17-12(10)8-13(11)16-4/h5-8H,1-4H3

InChI Key

WXVLCNREBFDEKS-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ageratina adenophora	Plant	KNApSAcK
Ageratina conyzoides	Plant	KNApSAcK
Ageratina glechonophylla	LOTUS Database	35616633
Ageratina pichinchensis var. bustamenta	Plant	KNApSAcK
Ageratina scorodonoides	Plant	KNApSAcK
Ageratum conyzoides	LOTUS Database	35616633
Anthemis cotula	LOTUS Database	35616633
Baccharis salicifolia	LOTUS Database	35616633
Brasilia sickii	Plant	KNApSAcK
Encelia californica	Plant	KNApSAcK
Encelia canescens	LOTUS Database	35616633
Encelia farinosa	LOTUS Database	35616633
Eupatorium rugosum	LOTUS Database	35616633
Flourensia riparia	LOTUS Database	35616633
Flourensia riparia Grisebach	Plant	KNApSAcK
Flourensia thurifera	LOTUS Database	35616633
Helianthella quinquenervis	LOTUS Database	35616633
Helianthus hirsutus	LOTUS Database	35616633
Hemizonia congesta	Plant	KNApSAcK
Hemizonia fitchii	Plant	KNApSAcK
Lagascea rigida	Plant	KNApSAcK
Tithonia diversifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Acetophenone
Aryl alkyl ketone
Aryl ketone
Anisole
Alkyl aryl ether
Benzenoid
Ketone
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzopyran (CHEBI:4789 )

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	3.02	ALOGPS
logP	2.27	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	15.76	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.32 m³·mol⁻¹	ChemAxon
Polarizability	25.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00002426

Chemspider ID

Not Available

KEGG Compound ID

C09005

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Encecalin (NP0051415)

MOL for NP0051415 (Encecalin)

3D MOL for NP0051415 (Encecalin)

3D SDF for NP0051415 (Encecalin)

3D-SDF for NP0051415 (Encecalin)

PDB for NP0051415 (Encecalin)

3D PDB for NP0051415 (Encecalin)

SMILES for NP0051415 (Encecalin)

INCHI for NP0051415 (Encecalin)

Structure for NP0051415 (Encecalin)

3D Structure for NP0051415 (Encecalin)