NP-MRD: Showing NP-Card for Frutinone A (NP0051418)

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Record Information

Version

1.0

Created at

2022-04-27 22:47:34 UTC

Updated at

2022-04-27 22:47:34 UTC

NP-MRD ID

NP0051418

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Frutinone A

Description

Frutinone A belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Frutinone A is found in Polygala fruticosa . It was first documented in 2012 (PMID: 22533317). Based on a literature review a small amount of articles have been published on Frutinone A (PMID: 25252104) (PMID: 35341150) (PMID: 31921367) (PMID: 31341490).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200472D          

 20 23  0  0  0  0            999 V2000
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051418

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H8O4/c17-14-9-5-1-3-7-11(9)19-15-10-6-2-4-8-12(10)20-16(18)13(14)15/h1-8H

> <INCHI_KEY>
RFWULRHBGYKEEZ-UHFFFAOYSA-N

> <FORMULA>
C16H8O4

> <MOLECULAR_WEIGHT>
264.236

> <EXACT_MASS>
264.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
26.043877202383648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11,12-dihydro-5,10-dioxatetraphene-11,12-dione

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.2019015423333332

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4158288171027875

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
71.53420000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
frutinone A

> <JCHEM_VEBER_RULE>
0

$$$$

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       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.366   0.188   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.879   4.553   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.358   5.427   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.342   3.680   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₈O₄

Average Mass

264.2360 Da

Monoisotopic Mass

264.04226 Da

IUPAC Name

11,12-dihydro-5,10-dioxatetraphene-11,12-dione

Traditional Name

frutinone A

CAS Registry Number

Not Available

SMILES

O=C1OC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1O2

InChI Identifier

InChI=1S/C16H8O4/c17-14-9-5-1-3-7-11(9)19-15-10-6-2-4-8-12(10)20-16(18)13(14)15/h1-8H

InChI Key

RFWULRHBGYKEEZ-UHFFFAOYSA-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
Polygala fruticosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Chromone
Coumarin
Benzopyran
1-benzopyran
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:5179 )

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	3.17	ALOGPS
logP	2.2	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.53 m³·mol⁻¹	ChemAxon
Polarizability	26.04 Å³	ChemAxon
Number of Rings	4	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

C00002429

Chemspider ID

390534

KEGG Compound ID

C09008

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441965

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shin Y, Yoo C, Moon Y, Lee Y, Hong S: Efficient synthesis of frutinone A and its derivatives through palladium-catalyzed C - H activation/carbonylation. Chem Asian J. 2015 Apr;10(4):878-81. doi: 10.1002/asia.201402876. Epub 2014 Sep 22. [PubMed:25252104 ]
Gong F, Qu R, Yang Y, Li Y, Cheng Y, Zhang Q, Huang R, Fan Q, Dai J, Lv Y: The Mechanism of Ginseng and Astragalus Decoction in the Treatment of Malignant Pleural Effusion Based on Network Pharmacology and Molecular Docking Technology. Evid Based Complement Alternat Med. 2022 Mar 15;2022:7731402. doi: 10.1155/2022/7731402. eCollection 2022. [PubMed:35341150 ]
Li Q, Zhuang C, Wang D, Zhang W, Jia R, Sun F, Zhang Y, Du Y: Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A. Beilstein J Org Chem. 2019 Dec 12;15:2958-2965. doi: 10.3762/bjoc.15.291. eCollection 2019. [PubMed:31921367 ]
Hao J, Hu H, Liu J, Wang X, Liu X, Wang J, Niu M, Zhao Y, Xiao X: Integrated Metabolomics and Network Pharmacology Study on Immunoregulation Mechanisms of Panax ginseng through Macrophages. Evid Based Complement Alternat Med. 2019 Jun 25;2019:3630260. doi: 10.1155/2019/3630260. eCollection 2019. [PubMed:31341490 ]
Thelingwani RS, Dhansay K, Smith P, Chibale K, Masimirembwa CM: Potent inhibition of CYP1A2 by Frutinone A, an active ingredient of the broad spectrum antimicrobial herbal extract from P. fruticosa. Xenobiotica. 2012 Oct;42(10):989-1000. doi: 10.3109/00498254.2012.681077. Epub 2012 Apr 25. [PubMed:22533317 ]

Showing NP-Card for Frutinone A (NP0051418)

MOL for NP0051418 (Frutinone A)

3D MOL for NP0051418 (Frutinone A)

3D SDF for NP0051418 (Frutinone A)

3D-SDF for NP0051418 (Frutinone A)

PDB for NP0051418 (Frutinone A)

3D PDB for NP0051418 (Frutinone A)

SMILES for NP0051418 (Frutinone A)

INCHI for NP0051418 (Frutinone A)

Structure for NP0051418 (Frutinone A)

3D Structure for NP0051418 (Frutinone A)