NP-MRD: Showing NP-Card for 1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one (NP0285642)

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Record Information

Version

2.0

Created at

2022-09-09 13:54:10 UTC

Updated at

2022-09-09 13:54:10 UTC

NP-MRD ID

NP0285642

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one

Description

3-(4-Methoxyphenyl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. 3-(4-Methoxyphenyl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512312D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171512312D          

 41 44  0  0  0  0            999 V2000
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    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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  2  0  0  0  0
  4  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  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  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
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 17 38  2  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  2  0  0  0  0
  3 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285642

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CCC(=O)C2=C(O)C=C(O)C(C(C(C)C(C)CC3=CC=C(O)C=C3)C3=CC=C(O)C=C3)=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H36O7/c1-20(18-23-4-11-25(35)12-5-23)21(2)31(24-9-13-26(36)14-10-24)33-30(39)19-29(38)32(34(33)40)28(37)17-8-22-6-15-27(41-3)16-7-22/h4-7,9-16,19-21,31,35-36,38-40H,8,17-18H2,1-3H3

> <INCHI_KEY>
REHJYVNNHMTESF-UHFFFAOYSA-N

> <FORMULA>
C34H36O7

> <MOLECULAR_WEIGHT>
556.655

> <EXACT_MASS>
556.246103499

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.45408553354421

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(4-methoxyphenyl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
8.854665228999998

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.900150615132647

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.647981750786881

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3819008155577

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
159.43239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-methoxyphenyl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.005 -20.790   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.672 -21.560   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.672 -23.100   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.338 -20.790   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.669 -16.940   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   38                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   38                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
CONECT   31   18   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38   17   11   39                                                  
CONECT   39   38                                                            
CONECT   40    6   41                                                       
CONECT   41   40    3                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₆O₇

Average Mass

556.6550 Da

Monoisotopic Mass

556.24610 Da

IUPAC Name

3-(4-methoxyphenyl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

Traditional Name

3-(4-methoxyphenyl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CCC(=O)C2=C(O)C=C(O)C(C(C(C)C(C)CC3=CC=C(O)C=C3)C3=CC=C(O)C=C3)=C2O)C=C1

InChI Identifier

InChI=1S/C34H36O7/c1-20(18-23-4-11-25(35)12-5-23)21(2)31(24-9-13-26(36)14-10-24)33-30(39)19-29(38)32(34(33)40)28(37)17-8-22-6-15-27(41-3)16-7-22/h4-7,9-16,19-21,31,35-36,38-40H,8,17-18H2,1-3H3

InChI Key

REHJYVNNHMTESF-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Bis-desmethoxycurcumin
Dibenzylbutane lignan skeleton
Norlignan skeleton
2'-hydroxy-dihydrochalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Diphenylmethane
Alkyl-phenylketone
Acylphloroglucinol derivative
Butyrophenone
Benzenetriol
Phenylketone
Phenylpropane
Phloroglucinol derivative
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenoxy compound
Anisole
Benzoyl
Phenol ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Polyol
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	5.36	ALOGPS
logP	8.85	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	159.43 m³·mol⁻¹	ChemAxon
Polarizability	60.45 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

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 1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one (NP0285642)

MOL for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

3D MOL for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

3D SDF for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

3D-SDF for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

PDB for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

3D PDB for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

SMILES for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

INCHI for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

Structure for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)

3D Structure for NP0285642 (1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}-3-(4-methoxyphenyl)propan-1-one)