NP-MRD: Showing NP-Card for 6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one (NP0271518)

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Record Information

Version

2.0

Created at

2022-09-08 17:50:01 UTC

Updated at

2022-09-08 17:50:01 UTC

NP-MRD ID

NP0271518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one

Description

Gibepyrone 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. 6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one was first documented in 2015 (PMID: 26385195). Based on a literature review a small amount of articles have been published on Gibepyrone B (PMID: 27856636).

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-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  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₂O₃

Average Mass

180.2030 Da

Monoisotopic Mass

180.07864 Da

IUPAC Name

6-[(2E)-4-hydroxybut-2-en-2-yl]-3-methyl-2H-pyran-2-one

Traditional Name

6-[(2E)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H12O3/c1-7(5-6-11)9-4-3-8(2)10(12)13-9/h3-5,11H,6H2,1-2H3/b7-5+

InChI Key

VAFOLTKCMXTVQD-FNORWQNLSA-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 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
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	1.07	ChemAxon
pKa (Strongest Acidic)	15.6	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.42 m³·mol⁻¹	ChemAxon
Polarizability	19.29 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

8595202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10419772

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Janevska S, Arndt B, Niehaus EM, Burkhardt I, Rosler SM, Brock NL, Humpf HU, Dickschat JS, Tudzynski B: Gibepyrone Biosynthesis in the Rice Pathogen Fusarium fujikuroi Is Facilitated by a Small Polyketide Synthase Gene Cluster. J Biol Chem. 2016 Dec 30;291(53):27403-27420. doi: 10.1074/jbc.M116.753053. Epub 2016 Nov 17. [PubMed:27856636 ]
Li Y, Tang H, Tian X, Lin H, Wang M, Yao M: Three new cytotoxic isomalabaricane triterpenes from the marine sponge Stelletta tenuis. Fitoterapia. 2015 Oct;106:226-30. doi: 10.1016/j.fitote.2015.09.012. Epub 2015 Sep 15. [PubMed:26385195 ]
LOTUS database [Link]

Showing NP-Card for 6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one (NP0271518)

MOL for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

3D MOL for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

3D SDF for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

3D-SDF for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

PDB for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

3D PDB for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

SMILES for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

INCHI for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

Structure for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)

3D Structure for NP0271518 (6-[(2e)-4-hydroxybut-2-en-2-yl]-3-methylpyran-2-one)