NP-MRD: Showing NP-Card for 6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one (NP0152695)

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Record Information

Version

2.0

Created at

2022-09-02 09:13:35 UTC

Updated at

2022-09-02 09:13:35 UTC

NP-MRD ID

NP0152695

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one

Description

Argentilactone belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. 6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one was first documented in 2006 (PMID: 17050183). Based on a literature review a small amount of articles have been published on Argentilactone (PMID: 30150478) (PMID: 26734764) (PMID: 26150808) (PMID: 24752170).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    3.4122    1.2476    0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7656    0.1529    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809   -0.7173   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900    0.0528   -1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -0.8762   -1.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1662   -1.5087   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409   -1.3428    0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912   -0.5036   -0.6629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6850   -0.5004   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7874    0.3673    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9971    1.3760    1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352    1.6886    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409    2.6489    0.5575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8712    0.8427   -0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465    1.2911    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9575    1.1419    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8050    2.2232    0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672    0.5485   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5052   -0.5211    0.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -1.1735    0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -1.4810   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.8166   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297    0.6201   -1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8218   -1.7002   -1.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3923   -0.4108   -2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -2.1296    0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7832   -1.8410    1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501   -0.8797   -1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0086   -1.5333    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564   -0.0950   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5659    0.1735    1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0726    2.0225    2.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14  8  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
M  END


  Mrv1652309022211132D          

 14 14  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C1CC=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h6-8,10-11H,2-5,9H2,1H3/b8-6-

> <INCHI_KEY>
DSPGZXFLJQTNDA-VURMDHGXSA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.274

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.41838460980032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1Z)-hept-1-en-1-yl]-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
3.7812033416666666

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.526112218611953

> <JCHEM_PKA_STRONGEST_BASIC>
-6.809754604123182

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
58.912800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1Z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₈O₂

Average Mass

194.2740 Da

Monoisotopic Mass

194.13068 Da

IUPAC Name

6-[(1Z)-hept-1-en-1-yl]-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-[(1Z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C1CC=CC(=O)O1

InChI Identifier

InChI=1S/C12H18O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h6-8,10-11H,2-5,9H2,1H3/b8-6-

InChI Key

DSPGZXFLJQTNDA-VURMDHGXSA-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 dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	4.03	ALOGPS
logP	3.78	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	17.53	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.91 m³·mol⁻¹	ChemAxon
Polarizability	22.42 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

Not Available

Chemspider ID

4576092

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5463411

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Silva LDC, Tauhata SBF, Baeza LC, de Oliveira CMA, Kato L, Borges CL, de Almeida Soares CM, Pereira M: Argentilactone Molecular Targets in Paracoccidioides brasiliensis Identified by Chemoproteomics. Antimicrob Agents Chemother. 2018 Oct 24;62(11):e00737-18. doi: 10.1128/AAC.00737-18. Print 2018 Nov. [PubMed:30150478 ]
Araujo FS, Coelho LM, Silva Ldo C, da Silva Neto BR, Parente-Rocha JA, Bailao AM, de Oliveira CM, Fernandes Gda R, Hernandez O, Ochoa JG, Soares CM, Pereira M: Effects of Argentilactone on the Transcriptional Profile, Cell Wall and Oxidative Stress of Paracoccidioides spp. PLoS Negl Trop Dis. 2016 Jan 6;10(1):e0004309. doi: 10.1371/journal.pntd.0004309. eCollection 2016 Jan. [PubMed:26734764 ]
Prado RS, Bailao AM, Silva LC, de Oliveira CM, Marques MF, Silva LP, Silveira-Lacerda EP, Lima AP, Soares CM, Pereira M: Proteomic profile response of Paracoccidioides lutzii to the antifungal argentilactone. Front Microbiol. 2015 Jun 18;6:616. doi: 10.3389/fmicb.2015.00616. eCollection 2015. [PubMed:26150808 ]
Prado RS, Alves RJ, Oliveira CM, Kato L, Silva RA, Quintino GO, do Desterro Cunha S, de Almeida Soares CM, Pereira M: Inhibition of Paracoccidioides lutzii Pb01 isocitrate lyase by the natural compound argentilactone and its semi-synthetic derivatives. PLoS One. 2014 Apr 21;9(4):e94832. doi: 10.1371/journal.pone.0094832. eCollection 2014. [PubMed:24752170 ]
Cortes MJ, Armstrong V, Barrero AF, Bandoni AE, Priestap HA, Fournet A, Prina E: Configuration and leishmanicidal activity of (-)-argentilactone epoxides. Nat Prod Res. 2006 Sep;20(11):1008-14. doi: 10.1080/14786410600921391. [PubMed:17050183 ]
LOTUS database [Link]

Showing NP-Card for 6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one (NP0152695)

MOL for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

3D MOL for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

3D SDF for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

3D-SDF for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

PDB for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

3D PDB for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

SMILES for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

INCHI for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

Structure for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)

3D Structure for NP0152695 (6-[(1z)-hept-1-en-1-yl]-5,6-dihydropyran-2-one)