NP-MRD: Showing NP-Card for noonaphilone A (NP0333119)

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Record Information

Version

2.0

Created at

2024-05-09 18:37:59 UTC

Updated at

2025-07-30 22:23:46 UTC

NP-MRD ID

NP0333119

Natural Product DOI

https://doi.org/10.57994/2419

Secondary Accession Numbers

None

Natural Product Identification

Common Name

noonaphilone A

Description

Noonaphilone A belongs to the class of organic compounds known as m-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 3, respectively. Based on a literature review very few articles have been published on noonaphilone A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212321142D          

 31 33  0  0  1  0            999 V2000
   -1.0616   -2.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876   -2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015   -0.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7161   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169   -1.4747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5225   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9183    0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139    1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172    2.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9128    2.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161    3.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3117    3.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    4.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7106    5.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    6.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1095    6.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    6.4869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9129    7.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    0.8881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -1.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -0.0207    0.0000 O   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
  3  5  2  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
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 12  2  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 16 28  2  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END


  Mrv2104 01212321142D          

 31 33  0  0  1  0            999 V2000
   -1.0616   -2.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876   -2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015   -0.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7161   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169   -1.4747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5225   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9183    0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139    1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172    2.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9128    2.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161    3.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3117    3.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    4.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7106    5.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    6.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1095    6.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    6.4869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9129    7.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    0.8881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -1.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -0.0207    0.0000 O   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
  3  5  2  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
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 12  2  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 16 28  2  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333119

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=C(C)C(=O)[C@]3(C)OC(=O)C(C(=O)\C=C\C=C\C=C\C=C\C(O)=O)=C3C2=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C24H20O7/c1-14-12-16-15(2)22(28)24(3)21(17(16)13-30-14)20(23(29)31-24)18(25)10-8-6-4-5-7-9-11-19(26)27/h4-13H,1-3H3,(H,26,27)/b6-4+,7-5+,10-8+,11-9+/t24-/m1/s1

> <INCHI_KEY>
ZLROEGWGMUPBDW-UBWHLJHDSA-N

> <FORMULA>
C24H20O7

> <MOLECULAR_WEIGHT>
420.417

> <EXACT_MASS>
420.120902984

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
44.494763732634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-10-[(6aR)-3,5,6a-trimethyl-6,8-dioxo-6H,6aH,8H-furo[2,3-h]isochromen-9-yl]-10-oxodeca-2,4,6,8-tetraenoic acid

> <JCHEM_LOGP>
2.859373816333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.644815523647708

> <JCHEM_PKA_STRONGEST_BASIC>
-5.189236664901034

> <JCHEM_POLAR_SURFACE_AREA>
106.97

> <JCHEM_REFRACTIVITY>
119.96089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-10-[(6aR)-3,5,6a-trimethyl-6,8-dioxofuro[2,3-h]isochromen-9-yl]-10-oxodeca-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-23         0                                  
HETATM    1  O   UNK     0      -1.982  -5.419   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.170  -4.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.369  -4.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.097  -5.515   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.180  -2.849   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.452  -1.492   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.263  -0.183   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.803  -0.231   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.531  -1.588   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.070  -1.636   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.719  -2.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.898  -2.753   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.842  -3.970   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.087  -1.444   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.081  -0.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.714   1.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.826   2.294   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.459   3.789   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.571   4.855   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.203   6.350   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.315   7.416   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.948   8.912   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.060   9.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.693  11.473   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.804  12.539   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -7.283  12.109   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.437  14.034   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.235   1.658   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.507  -0.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.394  -2.386   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.816  -0.039   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5                                                       
CONECT   12    2   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14   16   29                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   16                                                            
CONECT   29   15   30   31                                                  
CONECT   30   29   12                                                       
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₀O₇

Average Mass

420.4170 Da

Monoisotopic Mass

420.12090 Da

IUPAC Name

(2E,4E,6E,8E)-10-[(6aR)-3,5,6a-trimethyl-6,8-dioxo-6H,6aH,8H-furo[2,3-h]isochromen-9-yl]-10-oxodeca-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-10-[(6aR)-3,5,6a-trimethyl-6,8-dioxofuro[2,3-h]isochromen-9-yl]-10-oxodeca-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C)C(=O)[C@]3(C)OC(=O)C(C(=O)\C=C\C=C\C=C\C=C\C(O)=O)=C3C2=CO1

InChI Identifier

InChI=1S/C24H20O7/c1-14-12-16-15(2)22(28)24(3)21(17(16)13-30-14)20(23(29)31-24)18(25)10-8-6-4-5-7-9-11-19(26)27/h4-13H,1-3H3,(H,26,27)/b6-4+,7-5+,10-8+,11-9+/t24-/m1/s1

InChI Key

ZLROEGWGMUPBDW-UBWHLJHDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	The University of Queensland	Thulasi Sritharan	2024-05-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	The University of Queensland	Thulasi Sritharan	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	The University of Queensland	Thulasi Sritharan	2024-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	The University of Queensland	Thulasi Sritharan	2024-05-09	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	The University of Queensland	Thulasi Sritharan	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	t.sritharan@uq.edu.au	The University of Queensland	Thulasi Sritharan	2024-05-09	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus noonimiae		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as m-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 3, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

M-quinomethanes

Alternative Parents

Substituents

M-quinomethane
Cyclohexenone
Alpha-acyloxy ketone
Short-chain keto acid
Heterocyclic fatty acid
Fatty acid ester
Branched fatty acid
Beta-keto acid
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Unsaturated fatty acid
Pyran
Keto acid
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Dihydrofuran
Acryloyl-group
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.86	ChemAxon
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.96 m³·mol⁻¹	ChemAxon
Polarizability	44.49 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	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

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

Showing NP-Card for noonaphilone A (NP0333119)

MOL for NP0333119 (noonaphilone A)

3D MOL for NP0333119 (noonaphilone A)

3D SDF for NP0333119 (noonaphilone A)

3D-SDF for NP0333119 (noonaphilone A)

PDB for NP0333119 (noonaphilone A)

3D PDB for NP0333119 (noonaphilone A)

SMILES for NP0333119 (noonaphilone A)

INCHI for NP0333119 (noonaphilone A)

Structure for NP0333119 (noonaphilone A)

3D Structure for NP0333119 (noonaphilone A)