NP-MRD: Showing NP-Card for (5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid (NP0327322)

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Record Information

Version

2.0

Created at

2022-09-12 09:48:11 UTC

Updated at

2022-09-12 09:48:11 UTC

NP-MRD ID

NP0327322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid

Description

Pafuranone A belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. Based on a literature review very few articles have been published on Pafuranone A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122211482D          

 38 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122211482D          

 38 40  0  0  1  0            999 V2000
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 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  2  0  0  0  0
 10 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 33 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0327322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C\C=C\[C@@]1(C)OC(C[C@@H](C)C2=C(C)OC(=O)C3=C2O[C@](C)(\C=C\C=C\CC)C3=O)=C(C(O)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O8/c1-7-9-11-13-15-29(5)25(31)22(27(33)34)20(37-29)17-18(3)21-19(4)36-28(35)23-24(21)38-30(6,26(23)32)16-14-12-10-8-2/h9-16,18H,7-8,17H2,1-6H3,(H,33,34)/b11-9+,12-10+,15-13+,16-14+/t18-,29-,30-/m1/s1

> <INCHI_KEY>
SEXVUFSUQVYADQ-BYZLVFGUSA-N

> <FORMULA>
C30H34O8

> <MOLECULAR_WEIGHT>
522.594

> <EXACT_MASS>
522.225368055

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.21828069504196

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-5-[(1E,3E)-hexa-1,3-dien-1-yl]-2-[(2R)-2-[(2R)-2-[(1E,3E)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxo-2H,3H,4H-furo[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid

> <JCHEM_LOGP>
5.6393967493333355

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.098521873752642

> <JCHEM_PKA_STRONGEST_BASIC>
-4.659156936133803

> <JCHEM_POLAR_SURFACE_AREA>
116.2

> <JCHEM_REFRACTIVITY>
149.91030000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-[(1E,3E)-hexa-1,3-dien-1-yl]-2-[(2R)-2-[(2R)-2-[(1E,3E)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.926   6.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.104   7.201   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.611   6.881   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.641   8.026   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.148   7.706   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.178   8.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.684   8.530   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.845  10.061   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.208   7.065   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.273   1.800   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.273  -0.260   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.192   0.215   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.336  -0.815   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.801  -0.339   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.945  -1.370   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.625  -2.876   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.700   7.065   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.165   6.589   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.485   5.083   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      11.309   7.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.224   8.530   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.130   9.776   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    9   37                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   31                                                  
CONECT   21   20   14   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   23   20   32                                                  
CONECT   32   31                                                            
CONECT   33   10   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   33    7   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₈

Average Mass

522.5940 Da

Monoisotopic Mass

522.22537 Da

IUPAC Name

(5R)-5-[(1E,3E)-hexa-1,3-dien-1-yl]-2-[(2R)-2-[(2R)-2-[(1E,3E)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxo-2H,3H,4H-furo[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid

Traditional Name

(5R)-5-[(1E,3E)-hexa-1,3-dien-1-yl]-2-[(2R)-2-[(2R)-2-[(1E,3E)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC\C=C\C=C\[C@@]1(C)OC(C[C@@H](C)C2=C(C)OC(=O)C3=C2O[C@](C)(\C=C\C=C\CC)C3=O)=C(C(O)=O)C1=O

InChI Identifier

InChI=1S/C30H34O8/c1-7-9-11-13-15-29(5)25(31)22(27(33)34)20(37-29)17-18(3)21-19(4)36-28(35)23-24(21)38-30(6,26(23)32)16-14-12-10-8-2/h9-16,18H,7-8,17H2,1-6H3,(H,33,34)/b11-9+,12-10+,15-13+,16-14+/t18-,29-,30-/m1/s1

InChI Key

SEXVUFSUQVYADQ-BYZLVFGUSA-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 aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyranone
Alkyl aryl ether
Pyran
3-furanone
Heteroaromatic compound
Vinylogous ester
Dihydrofuran
Cyclic ketone
Lactone
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	5.64	ChemAxon
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	149.91 m³·mol⁻¹	ChemAxon
Polarizability	56.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

80564754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146683577

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid (NP0327322)

MOL for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

3D MOL for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

3D SDF for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

3D-SDF for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

PDB for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

3D PDB for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

SMILES for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

INCHI for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

Structure for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)

3D Structure for NP0327322 ((5r)-5-[(1e,3e)-hexa-1,3-dien-1-yl]-2-[(2r)-2-[(2r)-2-[(1e,3e)-hexa-1,3-dien-1-yl]-2,6-dimethyl-3,4-dioxofuro[3,2-c]pyran-7-yl]propyl]-5-methyl-4-oxofuran-3-carboxylic acid)