NP-MRD: Showing NP-Card for 4'-Hydroxy-2-O-methylanigorufone (NP0138363)

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Record Information

Version

1.0

Created at

2022-05-31 17:56:31 UTC

Updated at

2022-05-31 17:56:31 UTC

NP-MRD ID

NP0138363

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-Hydroxy-2-O-methylanigorufone

Description

9-(4-Hydroxyphenyl)-2-methoxy-1H-phenalen-1-one belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. 9-(4-Hydroxyphenyl)-2-methoxy-1H-phenalen-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 9-(4-Hydroxyphenyl)-2-methoxy-1H-phenalen-1-one has been detected, but not quantified in, fruits. This could make 9-(4-hydroxyphenyl)-2-methoxy-1H-phenalen-1-one a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -2.6547    3.8378    0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014    3.1984   -0.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6879    1.8111   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7676    1.0607   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023   -0.3713   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -1.0726   -0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092   -2.4416   -0.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7047   -3.0969   -0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5085   -2.4016   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161   -3.0830   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8539   -2.3816   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -0.9800   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.2968    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1363   -0.4355   -0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865    0.1295   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736    0.8708    0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9402    1.4556    0.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235    1.0210    1.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4733    0.4406    1.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161   -0.3412   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5164   -1.0325   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947    1.1010   -0.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    1.7801   -0.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5797    4.9234    0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6532    3.4365    0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732    3.5145    1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381    1.5691   -0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8237   -0.5461   -0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8555   -2.9745   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969   -4.1769   -0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443   -4.1617   -0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -2.8975    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506   -1.0131   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1574    0.0283   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250    1.3384   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9520    1.6092    2.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7420    0.5785    2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 21  1  0
 21 20  2  0
 20 22  1  0
 22 23  2  0
 20 12  1  0
 12 11  2  0
 11 10  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 22  3  1  0
 19 13  1  0
 21  5  1  0
 10  9  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
 11 32  1  0
 10 31  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv0541 05061308002D          

 23 26  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 14  4  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  2  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 15  1  0  0  0  0
 22 20  2  0  0  0  0
 23  1  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138363

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=CC=CC3=C2C(C1=O)=C(C=C3)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O3/c1-23-17-11-14-4-2-3-13-7-10-16(19(18(13)14)20(17)22)12-5-8-15(21)9-6-12/h2-11,21H,1H3

> <INCHI_KEY>
PXMSSFOVGYLJLV-UHFFFAOYSA-N

> <FORMULA>
C20H14O3

> <MOLECULAR_WEIGHT>
302.3234

> <EXACT_MASS>
302.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.365830376050376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(4-hydroxyphenyl)-2-methoxy-1H-phenalen-1-one

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
3.8443859979999995

> <ALOGPS_LOGS>
-5.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.315775396640333

> <JCHEM_PKA_STRONGEST_BASIC>
-4.925304593076627

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
91.10489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(4-hydroxyphenyl)-2-methoxyphenalen-1-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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    3    4                                                       
CONECT    3    2   13                                                       
CONECT    4    2   14                                                       
CONECT    5    8   12                                                       
CONECT    6    9   12                                                       
CONECT    7   10   13                                                       
CONECT    8    5   15                                                       
CONECT    9    6   15                                                       
CONECT   10    7   16                                                       
CONECT   11   14   17                                                       
CONECT   12    5    6   16                                                  
CONECT   13    3    7   18                                                  
CONECT   14    4   11   18                                                  
CONECT   15    8    9   21                                                  
CONECT   16   10   12   19                                                  
CONECT   17   11   20   23                                                  
CONECT   18   13   14   19                                                  
CONECT   19   16   18   20                                                  
CONECT   20   17   19   22                                                  
CONECT   21   15                                                            
CONECT   22   20                                                            
CONECT   23    1   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₄O₃

Average Mass

302.3234 Da

Monoisotopic Mass

302.09429 Da

IUPAC Name

9-(4-hydroxyphenyl)-2-methoxy-1H-phenalen-1-one

Traditional Name

9-(4-hydroxyphenyl)-2-methoxyphenalen-1-one

CAS Registry Number

204134-70-3

SMILES

COC1=CC2=CC=CC3=C2C(C1=O)=C(C=C3)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H14O3/c1-23-17-11-14-4-2-3-13-7-10-16(19(18(13)14)20(17)22)12-5-8-15(21)9-6-12/h2-11,21H,1H3

InChI Key

PXMSSFOVGYLJLV-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 phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Phenalen-1-one
Phenalen
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.66	ALOGPS
logP	3.84	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.1 m³·mol⁻¹	ChemAxon
Polarizability	32.37 Å³	ChemAxon
Number of Rings	4	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

HMDB0034690

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013220

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

71358480

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4'-Hydroxy-2-O-methylanigorufone (NP0138363)

MOL for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

3D MOL for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

3D SDF for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

3D-SDF for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

PDB for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

3D PDB for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

SMILES for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

INCHI for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

Structure for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)

3D Structure for NP0138363 (4'-Hydroxy-2-O-methylanigorufone)