NP-MRD: Showing NP-Card for Knemolone C (NP0333018)

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Record Information

Version

2.0

Created at

2024-05-03 08:58:39 UTC

Updated at

2026-02-06 05:03:24 UTC

NP-MRD ID

NP0333018

Natural Product DOI

https://doi.org/10.57994/2311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Knemolone C

Description

Knemolone C belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Knemolone C was first documented in 2025 (PMID: 40860039). Based on a literature review very few articles have been published on Knemolone C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01152311352D          

 23 24  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  3  7  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 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
 14 19  1  0  0  0  0
  7 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333018

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O)C=C(O)C=C1CCCCCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O3/c1-15(21)20-17(13-18(22)14-19(20)23)12-8-3-2-5-9-16-10-6-4-7-11-16/h4,6-7,10-11,13-14,22-23H,2-3,5,8-9,12H2,1H3

> <INCHI_KEY>
RDAVYEVHHQTOBN-UHFFFAOYSA-N

> <FORMULA>
C20H24O3

> <MOLECULAR_WEIGHT>
312.409

> <EXACT_MASS>
312.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.05211577726192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[2,4-dihydroxy-6-(6-phenylhexyl)phenyl]ethan-1-one

> <JCHEM_LOGP>
5.888400043333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.954593209874819

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.976598622158991

> <JCHEM_PKA_STRONGEST_BASIC>
-4.907553740436256

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
93.16480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-[2,4-dihydroxy-6-(6-phenylhexyl)phenyl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JAN-23         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    7   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₃

Average Mass

312.4090 Da

Monoisotopic Mass

312.17254 Da

IUPAC Name

1-[2,4-dihydroxy-6-(6-phenylhexyl)phenyl]ethan-1-one

Traditional Name

1-[2,4-dihydroxy-6-(6-phenylhexyl)phenyl]ethanone

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)C=C(O)C=C1CCCCCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C20H24O3/c1-15(21)20-17(13-18(22)14-19(20)23)12-8-3-2-5-9-16-10-6-4-7-11-16/h4,6-7,10-11,13-14,22-23H,2-3,5,8-9,12H2,1H3

InChI Key

RDAVYEVHHQTOBN-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-03	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.17 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	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, 600.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.17, CDCl₃, simulated)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Knema oblongifolia		Not Available
Knema oblongifolia		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acetophenone
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	5.89	ChemAxon
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	93.16 m³·mol⁻¹	ChemAxon
Polarizability	36.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Kirchhoffer OA, Nitschke J, Luscher A, Nothias LF, Marcourt L, Hanna N, Grondin A, Kohler T, Ferreira Queiroz E, Soldati T, Wolfender JL: Phenylalkyl Acetophenones and Anacardic Acids from Knema oblongifolia with Synthetic Analogues as Anti-infectives and Antibacterial Agents. ACS Bio Med Chem Au. 2025 Jun 9;5(4):650-664. doi: 10.1021/acsbiomedchemau.5c00052. eCollection 2025 Aug 20. [PubMed:40860039 ]
DOI: 10.1021/acsbiomedchemau.5c00052
PMID: 40860039

Showing NP-Card for Knemolone C (NP0333018)

MOL for NP0333018 (Knemolone C)

3D MOL for NP0333018 (Knemolone C)

3D SDF for NP0333018 (Knemolone C)

3D-SDF for NP0333018 (Knemolone C)

PDB for NP0333018 (Knemolone C)

3D PDB for NP0333018 (Knemolone C)

SMILES for NP0333018 (Knemolone C)

INCHI for NP0333018 (Knemolone C)

Structure for NP0333018 (Knemolone C)

3D Structure for NP0333018 (Knemolone C)