NP-MRD: Showing NP-Card for 2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one (NP0305566)

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Record Information

Version

2.0

Created at

2022-09-10 21:29:48 UTC

Updated at

2022-09-10 21:29:49 UTC

NP-MRD ID

NP0305566

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

Description

2-{[5,7-Dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)-2H-chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-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. 2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one is found in Hypericum brasiliense. 2-{[5,7-Dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)-2H-chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241512462D          

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M  END

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M  END


  Mrv1533004241512462D          

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 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 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
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 15 33  1  0  0  0  0
 26 33  2  0  0  0  0
 13 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
 12 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305566

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1=C(O)C2=C(OC(C)(C)C=C2)C(CC2=C(O)C(C)(C)C(O)=C(C(=O)C(C)C)C2=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O8/c1-12(2)19(29)17-21(31)14-9-10-27(5,6)36-24(14)15(22(17)32)11-16-23(33)18(20(30)13(3)4)26(35)28(7,8)25(16)34/h9-10,12-13,31-32,34-35H,11H2,1-8H3

> <INCHI_KEY>
NZWBKTCISFAVGY-UHFFFAOYSA-N

> <FORMULA>
C28H34O8

> <MOLECULAR_WEIGHT>
498.572

> <EXACT_MASS>
498.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.900874947240425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)-2H-chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
6.2581899283333335

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.748523438449192

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.10298537964575

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6824165926267485

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
139.08159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.850  -5.657   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.860  -3.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.195  -3.757   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.905  -3.374   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   34                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   36                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   33                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   33                                                       
CONECT   33   32   15   26                                                  
CONECT   34   13    6   35                                                  
CONECT   35   34                                                            
CONECT   36   12                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₈

Average Mass

498.5720 Da

Monoisotopic Mass

498.22537 Da

IUPAC Name

2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)-2H-chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

Traditional Name

2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1=C(O)C2=C(OC(C)(C)C=C2)C(CC2=C(O)C(C)(C)C(O)=C(C(=O)C(C)C)C2=O)=C1O

InChI Identifier

InChI=1S/C28H34O8/c1-12(2)19(29)17-21(31)14-9-10-27(5,6)36-24(14)15(22(17)32)11-16-23(33)18(20(30)13(3)4)26(35)28(7,8)25(16)34/h9-10,12-13,31-32,34-35H,11H2,1-8H3

InChI Key

NZWBKTCISFAVGY-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
Hypericum brasiliense	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
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Benzenoid
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Ether
Enol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
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	3.53	ALOGPS
logP	6.26	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.08 m³·mol⁻¹	ChemAxon
Polarizability	52.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one (NP0305566)

MOL for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D MOL for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D SDF for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D-SDF for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

PDB for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D PDB for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

SMILES for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

INCHI for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

Structure for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D Structure for NP0305566 (2-{[5,7-dihydroxy-2,2-dimethyl-6-(2-methylpropanoyl)chromen-8-yl]methyl}-3,5-dihydroxy-4,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)