NP-MRD: Showing NP-Card for peniapyrone A (NP0333314)

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Record Information

Version

2.0

Created at

2024-05-30 03:45:11 UTC

Updated at

2024-11-01 01:36:21 UTC

NP-MRD ID

NP0333314

Natural Product DOI

https://doi.org/10.57994/2672

Secondary Accession Numbers

None

Natural Product Identification

Common Name

peniapyrone A

Description

Peniapyrone A 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. Based on a literature review very few articles have been published on peniapyrone A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02112306212D          

 19 21  0  0  1  0            999 V2000
    4.0716    1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124    2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878    2.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5978    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7732    1.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2406    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    2.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    0.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    2.1727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1632    2.1984    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286    2.8997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2940    3.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425    0.0689    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  0  0  0  0
  7  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
  7 12  1  1  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  5 17  1  0  0  0  0
  6 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@H](O)OC3=C(C(=O)OC(C)=C3)[C@]1(C)C=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O5/c1-6-5-8-10(12(16)17-6)13(2)4-3-7(14)9(13)11(15)18-8/h3-5,9,11,15H,1-2H3/t9-,11-,13-/m1/s1

> <INCHI_KEY>
KBXYZFUVYISFDW-IRUJWGPZSA-N

> <FORMULA>
C13H12O5

> <MOLECULAR_WEIGHT>
248.234

> <EXACT_MASS>
248.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.81273140651543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,6S,7R)-7-hydroxy-2,11-dimethyl-8,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),3,10-triene-5,13-dione

> <JCHEM_LOGP>
0.7496798500000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.59677902943125

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.885226458569013

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1612019359383146

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
64.79220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6S,7R)-7-hydroxy-2,11-dimethyl-8,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),3,10-triene-5,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-FEB-23         0                                  
HETATM    1  C   UNK     0       7.600   2.939   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.061   2.891   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.333   1.534   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.250   4.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.711   4.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.983   2.795   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.443   2.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.449   1.571   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.977   2.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.863   3.689   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.040   4.683   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.113   1.360   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.632   4.056   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.171   4.104   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       1.360   5.413   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.549   6.722   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.899   5.461   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.794   1.486   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.066   0.129   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   18                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   12   13                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10                                                            
CONECT   12    7                                                            
CONECT   13    7   10   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5                                                       
CONECT   18    6    3   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₂O₅

Average Mass

248.2340 Da

Monoisotopic Mass

248.06847 Da

IUPAC Name

(2R,6S,7R)-7-hydroxy-2,11-dimethyl-8,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),3,10-triene-5,13-dione

Traditional Name

(2R,6S,7R)-7-hydroxy-2,11-dimethyl-8,12-dioxatricyclo[7.4.0.0^{2,6}]trideca-1(9),3,10-triene-5,13-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@H](O)OC3=C(C(=O)OC(C)=C3)[C@]1(C)C=CC2=O

InChI Identifier

InChI=1S/C13H12O5/c1-6-5-8-10(12(16)17-6)13(2)4-3-7(14)9(13)11(15)18-8/h3-5,9,11,15H,1-2H3/t9-,11-,13-/m1/s1

InChI Key

KBXYZFUVYISFDW-IRUJWGPZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C5D5N, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C5D5N, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, C2D6OS, simulated)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802, C2D6OS, simulated)	baiy@iae.ac.cn	Institute of Applied Ecology, Chinese Academy of Sciences	Yan Bai	2024-05-30	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
brefeldianum		Not Available
brefeldianum F4a		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pyranones and derivatives. These 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

B'-hydroxy-alpha,beta-unsaturated-ketone
Pyranone
Fatty acid ester
Fatty acyl
Beta-hydroxy ketone
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Enol ester
Acryloyl-group
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.75	ChemAxon
pKa (Strongest Acidic)	11.89	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	64.79 m³·mol⁻¹	ChemAxon
Polarizability	23.81 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for peniapyrone A (NP0333314)

MOL for NP0333314 (peniapyrone A)

3D MOL for NP0333314 (peniapyrone A)

3D SDF for NP0333314 (peniapyrone A)

3D-SDF for NP0333314 (peniapyrone A)

PDB for NP0333314 (peniapyrone A)

3D PDB for NP0333314 (peniapyrone A)

SMILES for NP0333314 (peniapyrone A)

INCHI for NP0333314 (peniapyrone A)

Structure for NP0333314 (peniapyrone A)

3D Structure for NP0333314 (peniapyrone A)