NP-MRD: Showing NP-Card for 2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one (NP0209286)

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Record Information

Version

2.0

Created at

2022-09-05 06:38:06 UTC

Updated at

2022-09-05 06:38:07 UTC

NP-MRD ID

NP0209286

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one

Description

2,5-Dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one is found in Diaporthe gulyae. Based on a literature review very few articles have been published on 2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -2.1372    1.0501    2.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6124    0.8288    1.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1706    0.8700    1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221    0.8831    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    0.8745    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039    1.1543   -0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    1.1561   -0.7653 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5774    1.0909   -2.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521   -0.0418   -0.1047 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0900   -1.1190   -0.9568 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3971   -1.5265   -1.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4207   -0.3672    1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7038   -1.3792    1.7876 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262    0.5681    1.7653 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7155   -0.0746    2.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    0.5274    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.5203    0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7736    0.2175   -0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5878   -0.8386   -0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4526   -1.1198   -1.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6248   -1.7504    0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990    1.2668    3.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1938    1.0149    2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915    1.3756   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145    2.0914   -0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2639    1.7423   -2.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237    0.2236    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3611   -2.3872   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9964   -0.7052   -1.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8335   -1.8870   -0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    1.4869    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359    0.5917    3.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2184   -0.4742   -0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335    1.3069   -0.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.2203    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2034    1.5270    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7353    0.8923   -1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3613   -2.1725   -2.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5147   -0.8676   -1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1183   -0.4895   -2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -2.1106    0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3191   -2.5856    0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9479   -1.1433    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  3  0
  3  2  1  0
  2  1  2  3
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
  5 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  2  0
 12  9  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
  9 27  1  1
  7 25  1  1
  8 26  1  0
  6 24  1  0
  1 22  1  0
  1 23  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 14 31  1  1
 15 32  1  0
M  END


  Mrv1652309052208382D          

 21 21  0  0  0  0            999 V2000
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    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
    2.1434   -0.4125    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
    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 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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  3  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209286

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(O)C=C(C#CC(=C)CCC=C(C)C)C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-11(2)6-5-7-12(3)8-9-13-10-14(18)17(21-4)16(20)15(13)19/h6,10,14-15,17-19H,3,5,7H2,1-2,4H3

> <INCHI_KEY>
RCJFBFLKNJWIDL-UHFFFAOYSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.359

> <EXACT_MASS>
290.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.603051341623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one

> <JCHEM_LOGP>
2.0250400750000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.722959747951641

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.828695296058205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4232273419720105

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
83.7282

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  12.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14                                                            
CONECT   16    2   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₄

Average Mass

290.3590 Da

Monoisotopic Mass

290.15181 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1C(O)C=C(C#CC(=C)CCC=C(C)C)C(O)C1=O

InChI Identifier

InChI=1S/C17H22O4/c1-11(2)6-5-7-12(3)8-9-13-10-14(18)17(21-4)16(20)15(13)19/h6,10,14-15,17-19H,3,5,7H2,1-2,4H3

InChI Key

RCJFBFLKNJWIDL-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
Diaporthe gulyae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Cyclitol or derivatives
Secondary alcohol
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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

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

163037439

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one (NP0209286)

MOL for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

3D MOL for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

3D SDF for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

3D-SDF for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

PDB for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

3D PDB for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

SMILES for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

INCHI for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

Structure for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)

3D Structure for NP0209286 (2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methylideneoct-6-en-1-yn-1-yl)cyclohex-3-en-1-one)