NP-MRD: Showing NP-Card for 1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione (NP0336424)

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Record Information

Version

2.0

Created at

2024-09-11 06:12:20 UTC

Updated at

2024-09-11 06:12:20 UTC

NP-MRD ID

NP0336424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione

Description

1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione has been detected, but not quantified in, herbs and spices. This could make 1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307182D          

 24 25  0  0  0  0            999 V2000
    3.5724    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 15  5  2  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 16  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  2  0  0  0  0
 21 17  2  0  0  0  0
 22 18  2  0  0  0  0
 23 19  1  0  0  0  0
 24  1  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(CCC(=O)CC(=O)CCC2=CC=CC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O4/c1-24-20-13-16(9-12-19(20)23)8-11-18(22)14-17(21)10-7-15-5-3-2-4-6-15/h2-6,9,12-13,23H,7-8,10-11,14H2,1H3

> <INCHI_KEY>
NMQRUGZIKWUACB-UHFFFAOYSA-N

> <FORMULA>
C20H22O4

> <MOLECULAR_WEIGHT>
326.3863

> <EXACT_MASS>
326.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.74990487924041

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptane-3,5-dione

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.4247141590000005

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.166483426177946

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.415854196038655

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889963169354681

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
93.17989999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptane-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668  14.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  12.320   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   15                                                       
CONECT    6    4   15                                                       
CONECT    7   10   15                                                       
CONECT    8   11   16                                                       
CONECT    9   12   16                                                       
CONECT   10    7   17                                                       
CONECT   11    8   18                                                       
CONECT   12    9   19                                                       
CONECT   13   16   20                                                       
CONECT   14   17   18                                                       
CONECT   15    5    6    7                                                  
CONECT   16    8    9   13                                                  
CONECT   17   10   14   21                                                  
CONECT   18   11   14   22                                                  
CONECT   19   12   20   23                                                  
CONECT   20   13   19   24                                                  
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24    1   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione, 9ci	HMDB

Chemical Formula

C₂₀H₂₂O₄

Average Mass

326.3863 Da

Monoisotopic Mass

326.15181 Da

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptane-3,5-dione

Traditional Name

1-(4-hydroxy-3-methoxyphenyl)-7-phenylheptane-3,5-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(CCC(=O)CC(=O)CCC2=CC=CC=C2)=C1

InChI Identifier

InChI=1S/C20H22O4/c1-24-20-13-16(9-12-19(20)23)8-11-18(22)14-17(21)10-7-15-5-3-2-4-6-15/h2-6,9,12-13,23H,7-8,10-11,14H2,1H3

InChI Key

NMQRUGZIKWUACB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Gingerdione
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1,3-diketone
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	3.64	ALOGPS
logP	4.42	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	93.18 m³·mol⁻¹	ChemAxon
Polarizability	35.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033710

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011826

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

13337758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione (NP0336424)

MOL for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

3D MOL for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

3D SDF for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

3D-SDF for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

PDB for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

3D PDB for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

SMILES for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

INCHI for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

Structure for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)

3D Structure for NP0336424 (1-(4-Hydroxy-3-methoxyphenyl)-7-phenyl-3,5-heptanedione)