NP-MRD: Showing NP-Card for methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate (NP0321294)

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Record Information

Version

2.0

Created at

2022-09-11 23:25:47 UTC

Updated at

2022-09-11 23:25:48 UTC

NP-MRD ID

NP0321294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate

Description

Phelligridin B belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate is found in Phellinus igniarius. methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate was first documented in 2019 (PMID: 31752824). Based on a literature review very few articles have been published on phelligridin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    7.1211    0.1477    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917    0.1139    0.7348 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0049    0.1604   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6522    0.2352   -1.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5464    0.1247   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7938    0.0430    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4083   -0.0088    1.8935 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4032    0.0139    0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7706    0.0635   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    0.0355   -0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740   -0.0414    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9418   -0.0729    0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5942   -0.0243   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819   -0.0544   -1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7317   -0.1372   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1074   -0.1656   -0.2811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0915   -0.1862    1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8265   -0.2690    2.2386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7000   -0.1552    1.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.1423   -1.7668 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795    0.1725   -1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5409    0.2489   -2.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4381    1.1668    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4188   -0.6113    1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5615   -0.1287   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -0.0692    2.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8361   -0.0513    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0436    0.0804   -1.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -0.0855    1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    0.0400   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4554   -0.0137   -2.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7610   -0.2227    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8290   -0.2945    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2281   -0.1968    2.1605 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 20  1  0
 20 21  1  0
 21 22  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 21  5  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv1652309122201252D          

 22 23  0  0  0  0            999 V2000
    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 O   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   -1.2375    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
    2.8579   -2.4750    0.0000 O   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   -4.1250    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
    2.1434   -5.3625    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   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
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0321294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(O)C=C(OC1=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O7/c1-21-14(19)13-12(18)7-9(22-15(13)20)4-2-8-3-5-10(16)11(17)6-8/h2-7,16-18H,1H3/b4-2+

> <INCHI_KEY>
ONQOQEBOMCDRPX-DUXPYHPUSA-N

> <FORMULA>
C15H12O7

> <MOLECULAR_WEIGHT>
304.254

> <EXACT_MASS>
304.058302726

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.754368655671016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxo-2H-pyran-3-carboxylate

> <JCHEM_LOGP>
1.8860023199999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.248199656072728

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.49402595487907

> <JCHEM_PKA_STRONGEST_BASIC>
-6.280777058624349

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
78.7947

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -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       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20    9   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₇

Average Mass

304.2540 Da

Monoisotopic Mass

304.05830 Da

IUPAC Name

methyl 6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxo-2H-pyran-3-carboxylate

Traditional Name

methyl 6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(O)C=C(OC1=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H12O7/c1-21-14(19)13-12(18)7-9(22-15(13)20)4-2-8-3-5-10(16)11(17)6-8/h2-7,16-18H,1H3/b4-2+

InChI Key

ONQOQEBOMCDRPX-DUXPYHPUSA-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
Phellinus igniarius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Vinylogous acid
Methyl ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	1.89	ChemAxon
pKa (Strongest Acidic)	5.49	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.79 m³·mol⁻¹	ChemAxon
Polarizability	29.75 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

23327028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54729711

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tapfuma KI, Uche-Okereafor N, Sebola TE, Hussan R, Mekuto L, Makatini MM, Green E, Mavumengwana V: Cytotoxic activity of crude extracts from Datura stramonium's fungal endophytes against A549 lung carcinoma and UMG87 glioblastoma cell lines and LC-QTOF-MS/MS based metabolite profiling. BMC Complement Altern Med. 2019 Nov 21;19(1):330. doi: 10.1186/s12906-019-2752-9. [PubMed:31752824 ]
LOTUS database [Link]

Showing NP-Card for methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate (NP0321294)

MOL for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

3D MOL for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

3D SDF for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

3D-SDF for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

PDB for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

3D PDB for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

SMILES for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

INCHI for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

Structure for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)

3D Structure for NP0321294 (methyl 6-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-carboxylate)