NP-MRD: Showing NP-Card for 4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (NP0189884)

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Record Information

Version

2.0

Created at

2022-09-04 06:27:10 UTC

Updated at

2022-09-04 06:27:10 UTC

NP-MRD ID

NP0189884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

Description

4-[(1S)-1-[(2R)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. 4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione is found in Kunzea baxteri. Based on a literature review very few articles have been published on 4-[(1S)-1-[(2R)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208272D          

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M  END

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M  END


  Mrv1652309042208272D          

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    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  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
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 26  2  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0189884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H](C1=C(O)C(C)=C(O)C2=C1O[C@H](CC2=O)C1=CC=CC=C1)C1=C(O)C(C)(C)C(=O)C(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H36O7/c1-15(2)13-18(22-27(35)30(4,5)29(37)31(6,7)28(22)36)21-24(33)16(3)25(34)23-19(32)14-20(38-26(21)23)17-11-9-8-10-12-17/h8-12,15,18,20,33-35H,13-14H2,1-7H3/t18-,20+/m0/s1

> <INCHI_KEY>
WKCSXMGLYRSJKO-AZUAARDMSA-N

> <FORMULA>
C31H36O7

> <MOLECULAR_WEIGHT>
520.622

> <EXACT_MASS>
520.246103499

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.795097439899806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1S)-1-[(2R)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

> <JCHEM_LOGP>
7.461836249666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.077675528189687

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.253930427217834

> <JCHEM_PKA_STRONGEST_BASIC>
-4.947569302157334

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
145.72159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S)-1-[(2R)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

> <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      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.707   5.257   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.677   5.800   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.657   5.800   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.518   2.577   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.528   0.863   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.865  -0.931   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   37                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   13   25                                                  
CONECT   25   24                                                            
CONECT   26    7    2   27                                                  
CONECT   27   26                                                            
CONECT   28    6   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   29   37                                                       
CONECT   37   36    5   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

C₃₁H₃₆O₇

Average Mass

520.6220 Da

Monoisotopic Mass

520.24610 Da

IUPAC Name

4-[(1S)-1-[(2R)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

Traditional Name

4-[(1S)-1-[(2R)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H](C1=C(O)C(C)=C(O)C2=C1O[C@H](CC2=O)C1=CC=CC=C1)C1=C(O)C(C)(C)C(=O)C(C)(C)C1=O

InChI Identifier

InChI=1S/C31H36O7/c1-15(2)13-18(22-27(35)30(4,5)29(37)31(6,7)28(22)36)21-24(33)16(3)25(34)23-19(32)14-20(38-26(21)23)17-11-9-8-10-12-17/h8-12,15,18,20,33-35H,13-14H2,1-7H3/t18-,20+/m0/s1

InChI Key

WKCSXMGLYRSJKO-AZUAARDMSA-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
Kunzea baxteri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Aromatic monoterpenoid
Chromane
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
1-benzopyran
Aryl alkyl ketone
Aryl ketone
M-benzoquinone
Quinone
Alkyl aryl ether
Cyclohexenone
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Cyclic ketone
Ether
Enol
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	7.46	ChemAxon
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.72 m³·mol⁻¹	ChemAxon
Polarizability	55.8 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	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

162977636

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (NP0189884)

MOL for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

3D MOL for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

3D SDF for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

3D-SDF for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

PDB for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

3D PDB for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

SMILES for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

INCHI for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

Structure for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)

3D Structure for NP0189884 (4-[(1s)-1-[(2r)-5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl]-3-methylbutyl]-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione)