Np mrd loader

Showing NP-Card for 9-Fluorenone (NP0002771)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2020-11-23 19:40:01 UTC
Updated at2021-08-12 19:52:06 UTC
NP-MRD IDNP0002771
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-Fluorenone
Provided ByBMRBBMRB logo
DescriptionFluoren-9-one is also known as 9-oxofluorene. 9-Fluorenone is found in Vitis vinifera. It was first documented in 1993 (PMID: 8328814). Based on a literature review a significant number of articles have been published on fluoren-9-one (PMID: 17984079) (PMID: 25756381) (PMID: 28079374) (PMID: 34016776).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002771 (9-Fluorenone)


     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.0000   -3.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6807   -1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844   -0.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209    1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    0.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    0.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537    1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6844   -0.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443   -2.7495    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517   -0.5200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2246    2.3331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    2.9569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902    2.9569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2246    2.3331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1517   -0.5200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1443   -2.7495    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  2  1  0
  8  3  1  0
 14  9  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
 13 22  1  0
M  END
Download

3D MOL for NP0002771 (9-Fluorenone)

NP0002771
     RDKit          3D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.3035    2.9562    0.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1662    1.7276    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772    0.7828    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464    0.8644    0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4828   -0.2298    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919   -1.4530    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5203   -1.5432   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893   -0.4478   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -0.2859   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -1.1910   -0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -0.7656   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4569    0.5555   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    1.4410   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    1.0408    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696    1.8402    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5462   -0.1024    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130   -2.3342   -0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670   -2.5111   -0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -2.2336   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -1.4885   -0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4970    0.8883   -0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320    2.4892    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  2  1  0
  8  3  1  0
 14  9  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
 13 22  1  0
M  END
Download

3D SDF for NP0002771 (9-Fluorenone)


     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.0000   -3.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6807   -1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844   -0.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209    1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    0.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    0.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537    1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6844   -0.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443   -2.7495    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517   -0.5200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2246    2.3331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    2.9569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902    2.9569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2246    2.3331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1517   -0.5200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1443   -2.7495    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  2  1  0
  8  3  1  0
 14  9  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
 13 22  1  0
M  END
> <DATABASE_ID>
NP0002771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C2=CC=CC=C2C2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H

> <INCHI_KEY>
YLQWCDOCJODRMT-UHFFFAOYSA-N

> <FORMULA>
C13H8O

> <MOLECULAR_WEIGHT>
180.206

> <EXACT_MASS>
180.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
19.490761944301514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9H-fluoren-9-one

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.1065783993333334

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.545454903944419

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
55.711700000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluorenone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002771 (9-Fluorenone)

NP0002771
     RDKit          3D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.3035    2.9562    0.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1662    1.7276    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772    0.7828    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464    0.8644    0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4828   -0.2298    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919   -1.4530    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5203   -1.5432   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893   -0.4478   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -0.2859   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -1.1910   -0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -0.7656   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4569    0.5555   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    1.4410   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    1.0408    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696    1.8402    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5462   -0.1024    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130   -2.3342   -0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670   -2.5111   -0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -2.2336   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -1.4885   -0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4970    0.8883   -0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320    2.4892    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  2  1  0
  8  3  1  0
 14  9  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
 13 22  1  0
M  END
Download

PDB for NP0002771 (9-Fluorenone)

HEADER    PROTEIN                                 21-JUL-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-15         0                                  
HETATM    1  C   UNK     0      27.312 -24.418   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.312 -22.878   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.621 -22.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.007 -22.878   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.007 -24.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.621 -25.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.625 -22.878   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.625 -24.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.316 -25.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.011 -22.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.320 -22.878   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.320 -24.418   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.011 -25.188   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      31.316 -26.728   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   10                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    5   14                                                  
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    9                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END
Download

3D PDB for NP0002771 (9-Fluorenone)

COMPND    NP0002771
HETATM    1  O1  UNL     1      -0.304   2.956   0.499  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.166   1.728   0.290  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.277   0.783   0.248  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.646   0.864   0.393  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.483  -0.230   0.300  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.892  -1.453   0.048  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.520  -1.543  -0.098  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.689  -0.448  -0.005  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.765  -0.286  -0.119  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.782  -1.191  -0.361  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.104  -0.766  -0.421  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.457   0.555  -0.246  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.425   1.441  -0.005  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.100   1.041   0.059  1.00  0.00           C  
HETATM   15  H1  UNL     1      -3.070   1.840   0.588  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.546  -0.102   0.423  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.513  -2.334  -0.031  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.067  -2.511  -0.296  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.516  -2.234  -0.501  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.894  -1.489  -0.612  1.00  0.00           H  
HETATM   21  H7  UNL     1       4.497   0.888  -0.293  1.00  0.00           H  
HETATM   22  H8  UNL     1       2.632   2.489   0.141  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4    4    8
CONECT    4    5   15
CONECT    5    6    6   16
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9
CONECT    9   10   10   14
CONECT   10   11   19
CONECT   11   12   12   20
CONECT   12   13   21
CONECT   13   14   14   22
END
Download

SMILES for NP0002771 (9-Fluorenone)

O=C1C2=CC=CC=C2C2=C1C=CC=C2
Download

INCHI for NP0002771 (9-Fluorenone)

InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
Download
View in JSmol
Synonyms
ValueSource
9-FluorenoneChEBI
9-OxofluoreneChEBI
9H-Fluoren-9-oneChEBI
Diphenylene ketoneChEBI
FluorenoneChEBI
Fluoren-9-oneMeSH
Chemical FormulaC13H8O
Average Mass180.2060 Da
Monoisotopic Mass180.05751 Da
IUPAC Name9H-fluoren-9-one
Traditional Namefluorenone
CAS Registry NumberNot Available
SMILES
O=C1C2=CC=CC=C2C2=C1C=CC=C2
InChI Identifier
InChI=1S/C13H8O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8H
InChI KeyYLQWCDOCJODRMT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vitis viniferaLOTUS Database
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.45ALOGPS
logP3.11ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.71 m³·mol⁻¹ChemAxon
Polarizability19.49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9824
KEGG Compound IDC06712
BioCyc ID9FLUORENONE
BiGG IDNot Available
Wikipedia LinkFluorenone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17922
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Pothuluri JV, Freeman JP, Evans FE, Cerniglia CE: Biotransformation of fluorene by the fungus Cunninghamella elegans. Appl Environ Microbiol. 1993 Jun;59(6):1977-80. doi: 10.1128/aem.59.6.1977-1980.1993. [PubMed:8328814 ]
  3. Li S, Zhang Q: Mechanistic studies on the dibenzofuran formation from phenanthrene, fluorene and 9-fluorenone. Int J Mol Sci. 2015 Mar 6;16(3):5271-84. doi: 10.3390/ijms16035271. [PubMed:25756381 ]
  4. Ghosh R, Mora AK, Nath S, Palit DK: Ultrafast Dynamics of Hydrogen Bond Breaking and Making in the Excited State of Fluoren-9-one: Time-Resolved Visible Pump-IR Probe Spectroscopic Study. J Phys Chem B. 2017 Feb 9;121(5):1068-1080. doi: 10.1021/acs.jpcb.6b11293. Epub 2017 Jan 30. [PubMed:28079374 ]
  5. Feng R, Zhang X, Murugesan V, Hollas A, Chen Y, Shao Y, Walter E, Wellala NPN, Yan L, Rosso KM, Wang W: Reversible ketone hydrogenation and dehydrogenation for aqueous organic redox flow batteries. Science. 2021 May 21;372(6544):836-840. doi: 10.1126/science.abd9795. [PubMed:34016776 ]