NP-MRD: Showing NP-Card for 5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one (NP0257954)

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Record Information

Version

2.0

Created at

2022-09-07 23:13:37 UTC

Updated at

2022-09-07 23:13:37 UTC

NP-MRD ID

NP0257954

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one

Description

5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 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. 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone has been detected, but not quantified in, herbs and spices. 5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one is found in Alpinia officinarum. This could make 5-hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.3940   -1.4272   -0.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7672   -0.3252   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1689   -0.0593   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0384   -1.2882   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4238   -0.9162    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3358   -0.4891   -0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6338   -0.1398   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0701   -0.2049    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1848   -0.6249    1.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857   -0.9734    1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    0.7815   -0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324    0.6737    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2645    0.7560    1.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0781    1.8131    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1132    1.9123   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0084    0.7606   -0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528   -0.3338   -1.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6552   -1.4075   -1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001   -1.3653   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6884   -2.4307   -0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0486   -0.2555    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1727    0.8079    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.2552    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658    0.7454   -0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556   -2.0745    0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0363   -1.7338   -1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9962   -0.4353   -1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3042    0.1858   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0934    0.0667    0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5337   -0.6767    2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1901   -1.3075    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.7476   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2977    1.7779   -0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -0.3308    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0521    1.6824    1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821    2.7505    0.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5566    1.7710    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7151    2.8239   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6328    2.0815   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656   -0.3436   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3889   -2.2406   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5279   -2.4432    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9651   -0.2426    0.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3888    1.6770    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12 11  1  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 22 16  1  0
 10  5  1  0
 13 35  1  0
 12 34  1  6
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 11 32  1  0
 11 33  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
M  END


  Mrv0541 05061307182D          

 22 23  0  0  0  0            999 V2000
   -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
    2.1434    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
    3.5724    5.3625    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
   -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
   -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
    3.5724    6.1875    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
    4.2868    6.6000    0.0000 O   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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 15  4  2  0  0  0  0
 15  5  1  0  0  0  0
 15  8  1  0  0  0  0
 16  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  2  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257954

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O3/c20-17-10-6-16(7-11-17)9-13-19(22)14-18(21)12-8-15-4-2-1-3-5-15/h1-7,10-11,19-20,22H,8-9,12-14H2

> <INCHI_KEY>
UNMNJFPAJOHXMT-UHFFFAOYSA-N

> <FORMULA>
C19H22O3

> <MOLECULAR_WEIGHT>
298.3762

> <EXACT_MASS>
298.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.86236740671298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
4.018857719

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.069758138404811

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.29597978348106

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7664892737995768

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
87.53899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one

> <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      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  10.010   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       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  12.320   0.000  0.00  0.00           O+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
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   15                                                       
CONECT    5    3   15                                                       
CONECT    6   10   16                                                       
CONECT    7   11   16                                                       
CONECT    8   12   15                                                       
CONECT    9   13   16                                                       
CONECT   10    6   17                                                       
CONECT   11    7   17                                                       
CONECT   12    8   18                                                       
CONECT   13    9   19                                                       
CONECT   14   18   19                                                       
CONECT   15    4    5    8                                                  
CONECT   16    6    7    9                                                  
CONECT   17   10   11   20                                                  
CONECT   18   12   14   21                                                  
CONECT   19   13   14   22                                                  
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₃

Average Mass

298.3762 Da

Monoisotopic Mass

298.15689 Da

IUPAC Name

5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one

Traditional Name

5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one

CAS Registry Number

Not Available

SMILES

OC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C19H22O3/c20-17-10-6-16(7-11-17)9-13-19(22)14-18(21)12-8-15-4-2-1-3-5-15/h1-7,10-11,19-20,22H,8-9,12-14H2

InChI Key

UNMNJFPAJOHXMT-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
Alpinia officinarum	LOTUS Database	35616633

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
Fatty alcohol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Beta-hydroxy ketone
Fatty acyl
Benzenoid
Secondary alcohol
Ketone
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen 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	3.47	ALOGPS
logP	4.02	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	10.3	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.54 m³·mol⁻¹	ChemAxon
Polarizability	33.86 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

HMDB0033711

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011827

KNApSAcK ID

Not Available

Chemspider ID

8215903

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10040339

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one (NP0257954)

MOL for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

3D MOL for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

3D SDF for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

3D-SDF for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

PDB for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

3D PDB for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

SMILES for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

INCHI for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

Structure for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)

3D Structure for NP0257954 (5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one)