NP-MRD: Showing NP-Card for (6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one (NP0145876)

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Record Information

Version

2.0

Created at

2022-09-02 01:09:41 UTC

Updated at

2022-09-02 01:09:41 UTC

NP-MRD ID

NP0145876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one

Description

(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. (6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one is found in Curcuma comosa and Curcuma kwangsiensis. The two aromatic rings are linked only by the heptane chain (6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -0.9292   -0.9988    1.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7866   -0.2258    0.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799    1.0854    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1098    0.9716    1.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322    0.1970    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2533    0.7551    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985    0.0700   -0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2767   -1.2389   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763   -1.8264   -1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3595   -1.0627   -1.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3959    0.2504   -1.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    0.8372   -0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209   -0.6304   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4152    0.0954   -1.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6411   -0.0214   -0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6170   -0.9700   -0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368   -0.9558    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9098    0.0218    1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0410    0.0382    2.0547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9519    0.9767    1.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8414    0.9486    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026    1.6481    1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0370    1.6684    0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9258    0.3688    2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806    1.9540    2.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593   -0.8405    0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.8168    0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -1.8312   -0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -2.8627   -1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1499   -1.5235   -2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2597    0.8564   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4351    1.8964   -0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325   -1.7209   -0.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3555   -0.3089   -1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -0.1846   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1349    1.1754   -1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4886   -1.7221   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5252   -1.6926    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9422   -0.5000    2.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0854    1.7524    2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119    1.7332    0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 21 15  1  0
 12  7  1  0
  5 26  1  0
  4 24  1  0
  4 25  1  0
  3 22  1  0
  3 23  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
M  END


  Mrv1652308221918262D          

 23 24  0  0  0  0            999 V2000
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.1250    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
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    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
   -4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 H   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
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 23  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCC(=O)CCC1=CC=C(O)C=C1)=C(\[H])C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O2/c20-18(13-10-17-11-14-19(21)15-12-17)9-5-4-8-16-6-2-1-3-7-16/h1-4,6-8,11-12,14-15,21H,5,9-10,13H2/b8-4+

> <INCHI_KEY>
HLXPZGZUVCDNGK-XBXARRHUSA-N

> <FORMULA>
C19H20O2

> <MOLECULAR_WEIGHT>
280.367

> <EXACT_MASS>
280.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.673427160760134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one

> <ALOGPS_LOGP>
4.72

> <JCHEM_LOGP>
4.970447129333333

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.505301777385094

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958296456431577

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.14009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.669   7.700   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      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  10.010   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -5.335   9.240   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -6.668   5.390   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8   22                                                  
CONECT    5    4    9                                                       
CONECT    6    2   16                                                       
CONECT    7    3   16                                                       
CONECT    8    4   16   23                                                  
CONECT    9    5   18                                                       
CONECT   10   13   17                                                       
CONECT   11   14   17                                                       
CONECT   12   15   17                                                       
CONECT   13   10   18                                                       
CONECT   14   11   19                                                       
CONECT   15   12   19                                                       
CONECT   16    6    7    8                                                  
CONECT   17   10   11   12                                                  
CONECT   18    9   13   20                                                  
CONECT   19   14   15   21                                                  
CONECT   20   18                                                            
CONECT   21   19                                                            
CONECT   22    4                                                            
CONECT   23    8                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₂

Average Mass

280.3670 Da

Monoisotopic Mass

280.14633 Da

IUPAC Name

(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one

Traditional Name

(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one

CAS Registry Number

Not Available

SMILES

[H]\C(CCC(=O)CCC1=CC=C(O)C=C1)=C(\[H])C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H20O2/c20-18(13-10-17-11-14-19(21)15-12-17)9-5-4-8-16-6-2-1-3-7-16/h1-4,6-8,11-12,14-15,21H,5,9-10,13H2/b8-4+

InChI Key

HLXPZGZUVCDNGK-XBXARRHUSA-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
Curcuma comosa	LOTUS Database	35616633
Curcuma kwangsiensis	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
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:70699 )
ketone (CHEBI:70699 )
diarylheptanoid (CHEBI:70699 )

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	4.72	ALOGPS
logP	4.97	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.14 m³·mol⁻¹	ChemAxon
Polarizability	32.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0133916

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23329049

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44560848

PDB ID

Not Available

ChEBI ID

70699

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one (NP0145876)

MOL for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

3D MOL for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

3D SDF for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

3D-SDF for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

PDB for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

3D PDB for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

SMILES for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

INCHI for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

Structure for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)

3D Structure for NP0145876 ((6e)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one)