NP-MRD: Showing NP-Card for (2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid (NP0215310)

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Record Information

Version

2.0

Created at

2022-09-05 14:53:33 UTC

Updated at

2022-09-05 14:53:33 UTC

NP-MRD ID

NP0215310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid

Description

Prolipyrone B belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. (2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid is found in Fusarium proliferatum. (2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid was first documented in 2018 (PMID: 30200525). Based on a literature review very few articles have been published on Prolipyrone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216532D          

 15 15  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/C(O)=O)C1=CC=C(CO)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O5/c1-6(4-9(12)13)8-3-2-7(5-11)10(14)15-8/h2-4,11H,5H2,1H3,(H,12,13)/b6-4+

> <INCHI_KEY>
QSBSCWLRCSPNST-GQCTYLIASA-N

> <FORMULA>
C10H10O5

> <MOLECULAR_WEIGHT>
210.185

> <EXACT_MASS>
210.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.0778197719946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[3-(hydroxymethyl)-2-oxo-2H-pyran-6-yl]but-2-enoic acid

> <JCHEM_LOGP>
0.10681606433333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.864473530808024

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.22064779143674

> <JCHEM_PKA_STRONGEST_BASIC>
-2.858085368141994

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
54.05810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₀O₅

Average Mass

210.1850 Da

Monoisotopic Mass

210.05282 Da

IUPAC Name

(2E)-3-[3-(hydroxymethyl)-2-oxo-2H-pyran-6-yl]but-2-enoic acid

Traditional Name

(2E)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid

CAS Registry Number

Not Available

SMILES

C\C(=C/C(O)=O)C1=CC=C(CO)C(=O)O1

InChI Identifier

InChI=1S/C10H10O5/c1-6(4-9(12)13)8-3-2-7(5-11)10(14)15-8/h2-4,11H,5H2,1H3,(H,12,13)/b6-4+

InChI Key

QSBSCWLRCSPNST-GQCTYLIASA-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
Fusarium proliferatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Lactone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Primary alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic alcohol
Alcohol
Hydrocarbon derivative
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	0.11	ChemAxon
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.06 m³·mol⁻¹	ChemAxon
Polarizability	20.08 Å³	ChemAxon
Number of Rings	1	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

29215530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71569922

PDB ID

Not Available

ChEBI ID

189328

Good Scents ID

Not Available

References

General References

Westphal KR, Muurmann AT, Paulsen IE, Norgaard KTH, Overgaard ML, Dall SM, Aalborg T, Wimmer R, Sorensen JL, Sondergaard TE: Who Needs Neighbors? PKS8 Is a Stand-Alone Gene in Fusarium graminearum Responsible for Production of Gibepyrones and Prolipyrone B. Molecules. 2018 Sep 2;23(9). pii: molecules23092232. doi: 10.3390/molecules23092232. [PubMed:30200525 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid (NP0215310)

MOL for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

3D MOL for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

3D SDF for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

3D-SDF for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

PDB for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

3D PDB for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

SMILES for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

INCHI for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

Structure for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)

3D Structure for NP0215310 ((2e)-3-[5-(hydroxymethyl)-6-oxopyran-2-yl]but-2-enoic acid)