NP-MRD: Showing NP-Card for 1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one (NP0190161)

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Record Information

Version

2.0

Created at

2022-09-04 06:46:49 UTC

Updated at

2022-09-04 06:46:49 UTC

NP-MRD ID

NP0190161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one

Description

1-(3-{[2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. 1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one is found in Agrimonia pilosa. Based on a literature review very few articles have been published on 1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208462D          

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 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 17 31  1  0  0  0  0
  9 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)C1=C(O)C(CC2=C(O)C=C(O)C3=C2OC(C(O)C3)C2=CC=C(O)C(O)=C2)=C(O)C(C)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O10/c1-4-5-18(30)23-25(36)16(24(35)12(2)26(23)37-3)9-14-19(31)11-20(32)15-10-22(34)27(38-28(14)15)13-6-7-17(29)21(33)8-13/h6-8,11,22,27,29,31-36H,4-5,9-10H2,1-3H3

> <INCHI_KEY>
UYBMYSLWGHMDRE-UHFFFAOYSA-N

> <FORMULA>
C28H30O10

> <MOLECULAR_WEIGHT>
526.538

> <EXACT_MASS>
526.183897166

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.34330101209753

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one

> <JCHEM_LOGP>
4.988272553333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.408913899001204

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.56122276449001

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2894313922789093

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
138.83379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   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  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+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
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.573   0.294   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.335   6.160   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   36                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   31                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21                                                       
CONECT   29   20   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   17                                                       
CONECT   32    9   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    6   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₁₀

Average Mass

526.5380 Da

Monoisotopic Mass

526.18390 Da

IUPAC Name

1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one

Traditional Name

1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one

CAS Registry Number

Not Available

SMILES

CCCC(=O)C1=C(O)C(CC2=C(O)C=C(O)C3=C2OC(C(O)C3)C2=CC=C(O)C(O)=C2)=C(O)C(C)=C1OC

InChI Identifier

InChI=1S/C28H30O10/c1-4-5-18(30)23-25(36)16(24(35)12(2)26(23)37-3)9-14-19(31)11-20(32)15-10-22(34)27(38-28(14)15)13-6-7-17(29)21(33)8-13/h6-8,11,22,27,29,31-36H,4-5,9-10H2,1-3H3

InChI Key

UYBMYSLWGHMDRE-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 catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
Linear 1,7-diphenylheptane skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Alkyl-phenylketone
Butyrophenone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenylketone
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Catechol
Aryl alkyl ketone
Aryl ketone
O-cresol
P-cresol
Phenol ether
Resorcinol
Toluene
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Secondary alcohol
Ketone
Organoheterocyclic compound
Polyol
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.99	ChemAxon
pKa (Strongest Acidic)	6.56	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.83 m³·mol⁻¹	ChemAxon
Polarizability	53.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

74977169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one (NP0190161)

MOL for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

3D MOL for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

3D SDF for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

3D-SDF for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

PDB for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

3D PDB for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

SMILES for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

INCHI for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

Structure for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)

3D Structure for NP0190161 (1-(3-{[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]methyl}-2,4-dihydroxy-6-methoxy-5-methylphenyl)butan-1-one)