NP-MRD: Showing NP-Card for 4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one (NP0245177)

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Record Information

Version

1.0

Created at

2022-09-07 06:09:31 UTC

Updated at

2022-09-07 06:09:31 UTC

NP-MRD ID

NP0245177

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one

Description

4-Hydroxy-6[4-hydroxystyryl]2-pyrone belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. 4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one is found in Phaeolepiota aurea. It was first documented in 2020 (PMID: 32936196). Based on a literature review a significant number of articles have been published on 4-hydroxy-6[4-hydroxystyryl]2-pyrone (PMID: 36061687) (PMID: 32905056) (PMID: 32789325) (PMID: 31809940).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208092D          

 17 18  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 O   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
    2.1434   -2.8875    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
    2.8579   -4.1250    0.0000 O   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
    0.0000   -4.1250    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
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    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   -6.6000    0.0000 O   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
    0.7145   -2.8875    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  7 17  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=CC2=CC(O)=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H10O4/c14-10-4-1-9(2-5-10)3-6-12-7-11(15)8-13(16)17-12/h1-8,14-15H

> <INCHI_KEY>
ORVQWHLMVLOZPX-UHFFFAOYSA-N

> <FORMULA>
C13H10O4

> <MOLECULAR_WEIGHT>
230.219

> <EXACT_MASS>
230.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.38014148125312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]-2H-pyran-2-one

> <JCHEM_LOGP>
2.2230971640000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.476945494888044

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.38835792313139

> <JCHEM_PKA_STRONGEST_BASIC>
-5.951770618045129

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
65.97040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-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       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667 -12.320   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  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₀O₄

Average Mass

230.2190 Da

Monoisotopic Mass

230.05791 Da

IUPAC Name

4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]-2H-pyran-2-one

Traditional Name

4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=CC2=CC(O)=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C13H10O4/c14-10-4-1-9(2-5-10)3-6-12-7-11(15)8-13(16)17-12/h1-8,14-15H

InChI Key

ORVQWHLMVLOZPX-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
Phaeolepiota aurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.22	ChemAxon
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.97 m³·mol⁻¹	ChemAxon
Polarizability	23.38 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

103871342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54680648

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Patel MS, Parekh JN, Chudasama DD, Patel HC, Dalwadi P, Kunjadiya A, Bhatt V, Ram KR: Meglumine-Promoted Eco-Compatible Pseudo-Three-Component Reaction for the Synthesis of 1,1-Dihomoarylmethane Scaffolds and Their Green Credentials. ACS Omega. 2022 Aug 18;7(34):30420-30439. doi: 10.1021/acsomega.2c03787. eCollection 2022 Aug 30. [PubMed:36061687 ]
Sharma S, Dutta NB, Bhuyan M, Das B, Baishya G: Correction: tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions. Org Biomol Chem. 2020 Sep 21;18(35):6965-6966. doi: 10.1039/d0ob90117b. Epub 2020 Sep 3. [PubMed:32936196 ]
Conlon TA, Fitzsimons PE, Borovickova I, Kirby F, Murphy S, Knerr I, Crushell E: Hypoglycemia is not a defining feature of metabolic crisis in mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase deficiency: Further evidence of specific biochemical markers which may aid diagnosis. JIMD Rep. 2020 Jun 30;55(1):26-31. doi: 10.1002/jmd2.12146. eCollection 2020 Sep. [PubMed:32905056 ]
Sharma S, Dutta NB, Bhuyan M, Das B, Baishya G: tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions. Org Biomol Chem. 2020 Aug 26;18(33):6537-6548. doi: 10.1039/d0ob01304h. [PubMed:32789325 ]
Bhat ZS, Rather MA, Ul Lah H, Hussain A, Maqbool M, Yousuf SK, Jabeen Z, Wani MA, Ahmad Z: In vitro bactericidal activity of 3-cinnamoyl-4-hydroxy-6-methyl-2-pyrone (CHP) against drug-susceptible, drug-resistant and drug-tolerant isolates of Mycobacterium tuberculosis. J Glob Antimicrob Resist. 2020 Sep;22:57-62. doi: 10.1016/j.jgar.2019.11.018. Epub 2019 Dec 3. [PubMed:31809940 ]
LOTUS database [Link]

Showing NP-Card for 4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one (NP0245177)

MOL for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

3D MOL for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

3D SDF for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

3D-SDF for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

PDB for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

3D PDB for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

SMILES for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

INCHI for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

Structure for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)

3D Structure for NP0245177 (4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one)