NP-MRD: Showing NP-Card for methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate (NP0169256)

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Record Information

Version

2.0

Created at

2022-09-03 05:10:38 UTC

Updated at

2022-09-03 05:10:38 UTC

NP-MRD ID

NP0169256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate

Description

Frutescin[Chrysanthemum] belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group. methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate is found in Argyranthemum adauctum, Argyranthemum frutescens and Glebionis segetum. Based on a literature review very few articles have been published on Frutescin[Chrysanthemum].

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    5.7918   -0.4574   -1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182   -0.3341   -0.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -0.2571   -0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401   -0.1969    0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765   -0.1707    1.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -0.1738    2.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946   -0.7578    1.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0835   -2.0638    1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0883   -2.5781    0.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107   -1.7647   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234   -0.4494   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355    0.3533   -1.2168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772   -0.1740   -2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164    0.0281    0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    1.4385    0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5729    2.3109    1.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0187    1.8382   -0.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813    3.2436   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5783   -1.3458   -2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7131   -0.6031   -1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9549    0.4610   -2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124   -0.7199    3.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408    0.8742    2.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -2.7353    2.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -3.5968    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4953   -2.1289   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200   -0.9744   -2.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216   -0.5772   -1.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3052    0.6461   -2.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975    3.7487   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3656    3.7106    0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    3.4061   -1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 11  2  0
 11 12  1  0
 12 13  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  3  0
  4  3  1  0
  3  2  3  0
  2  1  1  0
  7 14  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 10 26  1  0
  9 25  1  0
  8 24  1  0
  6 22  1  0
  6 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652309032207102D          

 18 18  0  0  0  0            999 V2000
    4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    0.0000    0.8250    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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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  2  1  0  0  0  0
  2  3  3  0  0  0  0
  3  4  1  0  0  0  0
  4  5  3  0  0  0  0
  5  6  1  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
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  7 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
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(OC)C=CC=C1CC#CC#CC

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-4-5-6-7-9-12-10-8-11-13(17-2)14(12)15(16)18-3/h8,10-11H,9H2,1-3H3

> <INCHI_KEY>
IAKJWTWZFAUOIR-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.615547308212548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.724729557999999

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889069285566773

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
71.31550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate

> <JCHEM_VEBER_RULE>
1

$$$$

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       8.002   7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    7   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2740 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate

Traditional Name

methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(OC)C=CC=C1CC#CC#CC

InChI Identifier

InChI=1S/C15H14O3/c1-4-5-6-7-9-12-10-8-11-13(17-2)14(12)15(16)18-3/h8,10-11H,9H2,1-3H3

InChI Key

IAKJWTWZFAUOIR-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, 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
Argyranthemum adauctum	LOTUS Database	35616633
Chrysanthemum frutescens	LOTUS Database	35616633
Chrysanthemum segetum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

O-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

O-methoxybenzoic acid or derivatives
Benzoate ester
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
Alkyl aryl ether
Methyl ester
Carboxylic acid ester
Ether
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	3.58	ALOGPS
logP	3.72	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.32 m³·mol⁻¹	ChemAxon
Polarizability	26.62 Å³	ChemAxon
Number of Rings	1	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

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

15559375

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate (NP0169256)

MOL for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

3D MOL for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

3D SDF for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

3D-SDF for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

PDB for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

3D PDB for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

SMILES for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

INCHI for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

Structure for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)

3D Structure for NP0169256 (methyl 2-(hexa-2,4-diyn-1-yl)-6-methoxybenzoate)