NP-MRD: Showing NP-Card for Nectriapyrone (NP0057276)

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Record Information

Version

2.0

Created at

2022-04-28 02:45:46 UTC

Updated at

2022-04-28 02:45:46 UTC

NP-MRD ID

NP0057276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nectriapyrone

Description

Nectriapyrone 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. Nectriapyrone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Nectriapyrone is found in Gymnostroma missouriensis, Gyrostroma missouriense, Nalanthamala vermoesenii and Phomopsis velata. Nectriapyrone was first documented in 2005 (PMID: 16042349). Based on a literature review a significant number of articles have been published on nectriapyrone (PMID: 19504381) (PMID: 25700035) (PMID: 26001271) (PMID: 27417331) (PMID: 34822596) (PMID: 30443971).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204452D          

 14 14  0  0  0  0            999 V2000
    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 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 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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)OC(=C1)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O3/c1-5-7(2)9-6-10(13-4)8(3)11(12)14-9/h5-6H,1-4H3/b7-5+

> <INCHI_KEY>
NRLCQITWKJENAT-FNORWQNLSA-N

> <FORMULA>
C11H14O3

> <MOLECULAR_WEIGHT>
194.23

> <EXACT_MASS>
194.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.14116518523891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(2E)-but-2-en-2-yl]-4-methoxy-3-methyl-2H-pyran-2-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.0618976633333337

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.835057871258801

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
57.284800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2E)-but-2-en-2-yl]-4-methoxy-3-methylpyran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.000   4.620   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6                                                            
CONECT   11    2   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₄O₃

Average Mass

194.2300 Da

Monoisotopic Mass

194.09429 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)OC(=C1)C(\C)=C\C

InChI Identifier

InChI=1S/C11H14O3/c1-5-7(2)9-6-10(13-4)8(3)11(12)14-9/h5-6H,1-4H3/b7-5+

InChI Key

NRLCQITWKJENAT-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gymnostroma missouriensis	-	KNApSAcK
Gyrostroma missouriense	-	KNApSAcK
Nalanthamala vermoesenii	LOTUS Database	35616633
Phomopsis velata	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
Alkyl aryl ether
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Ether
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	2.95	ALOGPS
logP	2.06	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.28 m³·mol⁻¹	ChemAxon
Polarizability	21.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00010346

Chemspider ID

4513676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5358550

PDB ID

Not Available

ChEBI ID

142639

Good Scents ID

Not Available

References

General References

Lu X, Xu N, Dai HF, Mei WL, Yang ZX, Pei YH: Three new compounds from endophytic fungus L10 of Cephalotaxus hainanensis. J Asian Nat Prod Res. 2009;11(5):397-400. doi: 10.1080/10286020902819947. [PubMed:19504381 ]
Andolfi A, Boari A, Evidente M, Cimmino A, Vurro M, Ash G, Evidente A: Gulypyrones A and B and Phomentrioloxins B and C Produced by Diaporthe gulyae, a Potential Mycoherbicide for Saffron Thistle (Carthamus lanatus). J Nat Prod. 2015 Apr 24;78(4):623-9. doi: 10.1021/np500570h. Epub 2015 Feb 20. [PubMed:25700035 ]
Gong T, Zhen X, Li BJ, Yang JL, Zhu P: Two new monoterpenoid alpha-pyrones from a fungus Nectria sp. HLS206 associated with the marine sponge Gelliodes carnosa. J Asian Nat Prod Res. 2015;17(6):633-7. doi: 10.1080/10286020.2015.1040778. Epub 2015 May 22. [PubMed:26001271 ]
He WJ, Zhou XJ, Qin XC, Mai YX, Lin XP, Liao SR, Yang B, Zhang T, Tu ZC, Wang JF, Liu Y: Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7. Nat Prod Res. 2017 Mar;31(5):604-609. doi: 10.1080/14786419.2016.1207076. Epub 2016 Jul 15. [PubMed:27417331 ]
Weber D, Gorzalczany S, Martino V, Acevedo C, Sterner O, Anke T: Metabolites from endophytes of the medicinal plant Erythrina crista-galli. Z Naturforsch C J Biosci. 2005 May-Jun;60(5-6):467-77. doi: 10.1515/znc-2005-5-616. [PubMed:16042349 ]
Masi M, Bashiri S, Cimmino A, Bahmani Z, Abdollahzadeh J, Evidente A: Phytotoxins Produced by Two Biscogniauxia rosacearum Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran. Toxins (Basel). 2021 Nov 18;13(11). pii: toxins13110812. doi: 10.3390/toxins13110812. [PubMed:34822596 ]
Motoyama T, Nogawa T, Hayashi T, Hirota H, Osada H: Induction of Nectriapyrone Biosynthesis in the Rice Blast Fungus Pyricularia oryzae by Disturbance of the Two-Component Signal Transduction System. Chembiochem. 2019 Mar 1;20(5):693-700. doi: 10.1002/cbic.201800620. Epub 2019 Jan 23. [PubMed:30443971 ]
Dos Santos R, Morais-Urano RP, Marcal RM, Silva GH, Santos MFC: Acetylcholinesterase and butyrylcholinesterase inhibition by nectriapyrone and tryptophol isolated from endophytic fungus Phomopsis sp. Nat Prod Res. 2022 Aug;36(16):4153-4158. doi: 10.1080/14786419.2021.1960327. Epub 2021 Sep 9. [PubMed:34498969 ]
Reveglia P, Pacetti A, Masi M, Cimmino A, Carella G, Marchi G, Mugnai L, Evidente A: Phytotoxic metabolites produced by Diaporthe eres involved in cane blight of grapevine in Italy. Nat Prod Res. 2021 Sep;35(17):2872-2880. doi: 10.1080/14786419.2019.1679133. Epub 2019 Nov 1. [PubMed:31674838 ]
Yang ZJ, Yin Y, Ge M: [A novel chromene with anti-tumor activities from fungus Phomopsis sp]. Zhongguo Zhong Yao Za Zhi. 2015 Feb;40(4):667-71. [PubMed:26137688 ]
Guimaraes DO, Borges WS, Kawano CY, Ribeiro PH, Goldman GH, Nomizo A, Thiemann OH, Oliva G, Lopes NP, Pupo MT: Biological activities from extracts of endophytic fungi isolated from Viguiera arenaria and Tithonia diversifolia. FEMS Immunol Med Microbiol. 2008 Jan;52(1):134-44. doi: 10.1111/j.1574-695X.2007.00354.x. Epub 2007 Dec 11. [PubMed:18081849 ]
Meister J, Weber D, Martino V, Sterner O, Anke T: Phomopsidone, a novel depsidone from an endophyte of the medicinal plant Eupatorium arnottianum. Z Naturforsch C J Biosci. 2007 Jan-Feb;62(1-2):11-5. doi: 10.1515/znc-2007-1-202. [PubMed:17425098 ]

Showing NP-Card for Nectriapyrone (NP0057276)

MOL for NP0057276 (Nectriapyrone)

3D MOL for NP0057276 (Nectriapyrone)

3D SDF for NP0057276 (Nectriapyrone)

3D-SDF for NP0057276 (Nectriapyrone)

PDB for NP0057276 (Nectriapyrone)

3D PDB for NP0057276 (Nectriapyrone)

SMILES for NP0057276 (Nectriapyrone)

INCHI for NP0057276 (Nectriapyrone)

Structure for NP0057276 (Nectriapyrone)

3D Structure for NP0057276 (Nectriapyrone)