NP-MRD: Showing NP-Card for 6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one (NP0263134)

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Record Information

Version

2.0

Created at

2022-09-08 06:13:09 UTC

Updated at

2022-09-08 06:13:09 UTC

NP-MRD ID

NP0263134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

Description

Agrimophol belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one is found in Agrimonia pilosa. Agrimophol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521542D          

 34 35  0  0  0  0            999 V2000
   -0.6804    0.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340    0.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340   -0.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -0.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630   -0.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -1.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630   -2.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630   -3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650   -4.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -4.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5202   -4.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327   -4.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -5.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -5.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309   -6.5707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -6.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915   -7.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9218   -8.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -5.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -5.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7683   -6.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7485   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6804   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340   -2.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804   -0.9450    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
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  9 10  1  0  0  0  0
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 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 18 20  1  0  0  0  0
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 17 24  1  0  0  0  0
 11 24  1  0  0  0  0
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 13 27  1  0  0  0  0
  9 28  2  0  0  0  0
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 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

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   -4.6308    1.6421    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5787    2.0382   -0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231521542D          

 34 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0263134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)C1=C(O)C(CC2(C)C(O)=C(C)C(O)=C(C(=O)C(C)CC)C2=O)=C(O)C(C)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O8/c1-8-10-16(27)17-22(31)15(20(29)13(4)23(17)34-7)11-26(6)24(32)14(5)21(30)18(25(26)33)19(28)12(3)9-2/h12,29-32H,8-11H2,1-7H3

> <INCHI_KEY>
NQGCBDWQKDAGTK-UHFFFAOYSA-N

> <FORMULA>
C26H34O8

> <MOLECULAR_WEIGHT>
474.55

> <EXACT_MASS>
474.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.35522705215846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
5.409467701666669

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.428045849208323

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7884708033079653

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6505973948193615

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
130.82009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.270   1.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.064   0.546   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.064  -0.994   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.397  -1.764   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.731  -0.994   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.397  -3.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.731  -4.074   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.065  -3.304   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.731  -5.614   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.065  -6.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.065  -7.924   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.548  -7.657   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.581  -7.657   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.571  -8.836   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.088  -8.569   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.044 -10.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.528 -10.551   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001 -11.998   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.484 -12.265   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.991 -13.178   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.508 -12.910   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.464 -14.625   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.454 -15.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.538  -9.371   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.021  -9.639   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.034 -11.463   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.108  -6.209   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.397  -6.384   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.397  -7.924   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.064  -5.614   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.270  -6.384   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.064  -4.074   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.270  -3.304   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.270  -1.764   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   32                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   24                                             
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   26                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   17   11   25                                                  
CONECT   25   24                                                            
CONECT   26   16                                                            
CONECT   27   13                                                            
CONECT   28    9   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₈

Average Mass

474.5500 Da

Monoisotopic Mass

474.22537 Da

IUPAC Name

6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

Traditional Name

6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

CCCC(=O)C1=C(O)C(CC2(C)C(O)=C(C)C(O)=C(C(=O)C(C)CC)C2=O)=C(O)C(C)=C1OC

InChI Identifier

InChI=1S/C26H34O8/c1-8-10-16(27)17-22(31)15(20(29)13(4)23(17)34-7)11-26(6)24(32)14(5)21(30)18(25(26)33)19(28)12(3)9-2/h12,29-32H,8-11H2,1-7H3

InChI Key

NQGCBDWQKDAGTK-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
Agrimonia pilosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Methoxyphenol
Phenoxy compound
O-cresol
P-cresol
Phenol ether
Resorcinol
Anisole
Methoxybenzene
Aryl alkyl ketone
Benzoyl
Alkyl aryl ether
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Cyclic ketone
Ether
Enol
Organic oxide
Hydrocarbon derivative
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	3.16	ALOGPS
logP	5.41	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.82 m³·mol⁻¹	ChemAxon
Polarizability	49.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

128292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one (NP0263134)

MOL for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D MOL for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D SDF for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D-SDF for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

PDB for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D PDB for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

SMILES for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

INCHI for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

Structure for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D Structure for NP0263134 (6-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-4,6-dimethyl-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)