NP-MRD: Showing NP-Card for (4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one (NP0323063)

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Record Information

Version

2.0

Created at

2022-09-12 02:15:20 UTC

Updated at

2022-09-12 02:15:20 UTC

NP-MRD ID

NP0323063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

Description

(4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one is found in Hagenia abyssinica.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122204152D          

 34 35  0  0  1  0            999 V2000
    1.4630   -0.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -0.9450    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340   -3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804   -3.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2481   -3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2822   -6.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5303   -6.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3209   -2.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -0.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309122204152D          

 34 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0323063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(O)=C(C[C@@]2(C)C(O)=C(C)C(=O)C(C(=O)C(C)C)=C2O)C(O)=C1C(=O)CC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O8/c1-11(2)9-16(27)17-22(31)15(20(29)13(5)23(17)34-8)10-26(7)24(32)14(6)21(30)18(25(26)33)19(28)12(3)4/h11-12,29,31-33H,9-10H2,1-8H3/t26-/m0/s1

> <INCHI_KEY>
ZGEBLIPEIZCKDH-SANMLTNESA-N

> <FORMULA>
C26H34O8

> <MOLECULAR_WEIGHT>
474.55

> <EXACT_MASS>
474.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.22232532328446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

> <JCHEM_LOGP>
5.251918133000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.6290560959537626

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.232616787662429

> <JCHEM_PKA_STRONGEST_BASIC>
-4.605219903296519

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
130.76769999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.731  -0.994   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.397  -1.764   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.397  -3.304   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.064  -4.074   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.270  -3.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.064  -5.614   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.270  -6.384   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.397  -6.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.397  -7.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.064  -8.694   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.463  -7.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.053  -9.874   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.570  -9.606   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.527 -11.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.517 -12.501   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.990 -11.588   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.517 -13.035   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.980 -10.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.496 -10.676   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.486  -9.496   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.023 -12.123   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.540 -12.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.033 -13.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.453  -8.961   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.443  -7.782   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.731  -5.614   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.065  -6.384   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.731  -4.074   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.065  -3.304   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.065  -1.764   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.398  -4.074   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.732  -3.304   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.066  -4.074   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.732  -1.764   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   24                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   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   10   25                                                  
CONECT   25   24                                                            
CONECT   26    8   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    3   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
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

(4S)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

Traditional Name

(4S)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(O)=C(C[C@@]2(C)C(O)=C(C)C(=O)C(C(=O)C(C)C)=C2O)C(O)=C1C(=O)CC(C)C

InChI Identifier

InChI=1S/C26H34O8/c1-11(2)9-16(27)17-22(31)15(20(29)13(5)23(17)34-8)10-26(7)24(32)14(6)21(30)18(25(26)33)19(28)12(3)4/h11-12,29,31-33H,9-10H2,1-8H3/t26-/m0/s1

InChI Key

ZGEBLIPEIZCKDH-SANMLTNESA-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
Hagenia abyssinica	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	5.25	ChemAxon
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	-4.6	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	8	ChemAxon
Refractivity	130.77 m³·mol⁻¹	ChemAxon
Polarizability	49.22 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one (NP0323063)

MOL for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D MOL for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D SDF for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D-SDF for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

PDB for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D PDB for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

SMILES for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

INCHI for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

Structure for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)

3D Structure for NP0323063 ((4s)-4-{[2,6-dihydroxy-4-methoxy-3-methyl-5-(3-methylbutanoyl)phenyl]methyl}-3,5-dihydroxy-2,4-dimethyl-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one)