NP-MRD: Showing NP-Card for fomentariol (NP0247900)

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Record Information

Version

2.0

Created at

2022-09-07 09:55:04 UTC

Updated at

2022-09-07 09:55:04 UTC

NP-MRD ID

NP0247900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fomentariol

Description

Fomentariol belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. fomentariol is found in Fomes fomentarius. fomentariol was first documented in 2015 (PMID: 26839505). Based on a literature review very few articles have been published on Fomentariol (PMID: 29675285).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    1.3863   -3.1926    0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -1.9823    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2475   -1.1506   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4996   -1.6914   -0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970    0.2047   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864    1.0705    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3484    0.7864    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110    1.7903    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6414    1.4014    0.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    0.8617   -1.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833    0.4360   -1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775   -0.5091   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.2482   -0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049    0.9544   -0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9848    1.2053   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4327    2.5283   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1286    3.2093   -0.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791   -1.1212    0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2423   -0.9526    0.8415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -2.2386    1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0653   -3.0781    1.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149   -2.4914    1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391   -3.5835    1.6093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802   -1.6184    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341   -2.6701    0.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209    2.1191   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4846   -0.2067    1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4943    1.8327    2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1832    2.7866    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2926    2.0923    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3351    1.8060   -1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7806    0.8472   -1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437    1.7647   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485    0.5502   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866    3.0699   -1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1106    2.2496   -2.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1700    2.7017    0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7873   -1.5806    1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325   -3.8993    2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3548   -4.0536    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
  2  1  2  0
  2 24  1  0
 24 22  2  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 20 18  2  0
 18 19  1  0
 18 13  1  0
 24 12  1  0
 17 37  1  0
 16 35  1  0
 16 36  1  0
 15 34  1  0
 14 33  1  0
 11 32  1  0
 10 31  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  4 25  1  0
 23 40  1  0
 21 39  1  0
 19 38  1  0
M  END


  Mrv1652309072211552D          

 24 25  0  0  0  0            999 V2000
    3.4479    1.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502    1.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0313   -0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8563   -0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2688   -1.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -1.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315   -1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -2.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -3.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -3.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    1.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
  2 24  1  0  0  0  0
 12 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC\C=C\C1=C2C=CC(\C=C\CO)=C(O)C(=O)C2=C(O)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O7/c18-7-1-3-9-5-6-10-11(4-2-8-19)14(21)17(24)16(23)12(10)15(22)13(9)20/h1-6,18-19,21,23-24H,7-8H2,(H,20,22)/b3-1+,4-2+

> <INCHI_KEY>
VWFRIRTWXNOGIL-ZPUQHVIOSA-N

> <FORMULA>
C17H16O7

> <MOLECULAR_WEIGHT>
332.308

> <EXACT_MASS>
332.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.76355954495283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,4,6-tetrahydroxy-1,7-bis[(1E)-3-hydroxyprop-1-en-1-yl]-5H-benzo[7]annulen-5-one

> <JCHEM_LOGP>
1.269146547666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.674528855301244

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.672732348824983

> <JCHEM_PKA_STRONGEST_BASIC>
2.8879675366338953

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
92.55749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,3,4,6-tetrahydroxy-1,7-bis[(1E)-3-hydroxyprop-1-en-1-yl]benzo[7]annulen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       6.436   2.729   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.779   1.228   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.280   0.885   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.240   2.089   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.948  -0.502   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.488  -0.502   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.258  -1.836   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.798  -1.836   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.568  -3.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.280  -1.890   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.779  -2.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.575  -1.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.241  -2.042   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.241  -3.582   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.907  -4.352   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.907  -5.892   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.241  -6.662   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.907  -1.272   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.574  -2.042   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.907   0.268   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.574   1.038   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.241   1.038   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.241   2.578   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.575   0.268   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    2   12                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₇

Average Mass

332.3080 Da

Monoisotopic Mass

332.08960 Da

IUPAC Name

2,3,4,6-tetrahydroxy-1,7-bis[(1E)-3-hydroxyprop-1-en-1-yl]-5H-benzo[7]annulen-5-one

Traditional Name

2,3,4,6-tetrahydroxy-1,7-bis[(1E)-3-hydroxyprop-1-en-1-yl]benzo[7]annulen-5-one

CAS Registry Number

Not Available

SMILES

OC\C=C\C1=C2C=CC(\C=C\CO)=C(O)C(=O)C2=C(O)C(O)=C1O

InChI Identifier

InChI=1S/C17H16O7/c18-7-1-3-9-5-6-10-11(4-2-8-19)14(21)17(24)16(23)12(10)15(22)13(9)20/h1-6,18-19,21,23-24H,7-8H2,(H,20,22)/b3-1+,4-2+

InChI Key

VWFRIRTWXNOGIL-ZPUQHVIOSA-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
Fomes fomentarius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Tropolone
Tropone
Styrene
Phenol
Benzenoid
Vinylogous acid
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	1.27	ChemAxon
pKa (Strongest Acidic)	6.67	ChemAxon
pKa (Strongest Basic)	2.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.56 m³·mol⁻¹	ChemAxon
Polarizability	33.76 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

10289311

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21675848

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maljuric N, Golubovic J, Ravnikar M, Zigon D, Strukelj B, Otasevic B: Isolation and Determination of Fomentariol: Novel Potential Antidiabetic Drug from Fungal Material. J Anal Methods Chem. 2018 Feb 20;2018:2434691. doi: 10.1155/2018/2434691. eCollection 2018. [PubMed:29675285 ]
Seo DW, Yi YJ, Lee MS, Yun BS, Lee SM: Differential Modulation of Lipopolysaccharide-Induced Inflammatory Cytokine Production by and Antioxidant Activity of Fomentariol in RAW264.7 Cells. Mycobiology. 2015 Dec;43(4):450-7. doi: 10.5941/MYCO.2015.43.4.450. Epub 2015 Dec 31. [PubMed:26839505 ]
LOTUS database [Link]

Showing NP-Card for fomentariol (NP0247900)

MOL for NP0247900 (fomentariol)

3D MOL for NP0247900 (fomentariol)

3D SDF for NP0247900 (fomentariol)

3D-SDF for NP0247900 (fomentariol)

PDB for NP0247900 (fomentariol)

3D PDB for NP0247900 (fomentariol)

SMILES for NP0247900 (fomentariol)

INCHI for NP0247900 (fomentariol)

Structure for NP0247900 (fomentariol)

3D Structure for NP0247900 (fomentariol)