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Showing NP-Card for 8-acetyl-7-hydroxychromen-2-one (NP0315580)

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Record Information
Version2.0
Created at2022-09-11 14:17:07 UTC
Updated at2022-09-11 14:17:08 UTC
NP-MRD IDNP0315580
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-acetyl-7-hydroxychromen-2-one
Description8-Acetyl-7-hydroxycoumarin belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. 8-acetyl-7-hydroxychromen-2-one was first documented in 2006 (PMID: 19127719). Based on a literature review a small amount of articles have been published on 8-Acetyl-7-hydroxycoumarin (PMID: 35892288) (PMID: 19243988).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0315580 (8-acetyl-7-hydroxychromen-2-one)


  Mrv1652309112216172D          

 15 16  0  0  0  0            999 V2000
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  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
 10 11  2  0  0  0  0
 11 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
  4 15  2  0  0  0  0
  9 15  1  0  0  0  0
M  END
Download

3D MOL for NP0315580 (8-acetyl-7-hydroxychromen-2-one)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -2.2624    1.5733    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1637    0.0750    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.5168    0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9075   -0.6332    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064   -1.9953    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -2.8132    0.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4620   -2.6094   -0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5624   -1.8185   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455   -0.4497   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5700    0.3742   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4723    1.7502   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986    2.2772   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1158    3.5330   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588    1.4959   -0.0100 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337    0.1806   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9585    1.9529   -0.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056    2.0201    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3616    1.8348    0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104   -2.5564    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804   -3.6889   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5424   -2.2406   -0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5275   -0.1116   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3537    2.3666   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4 15  2  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  5  4  1  0
  9 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 11 23  1  0
 10 22  1  0
  8 21  1  0
  7 20  1  0
  6 19  1  0
M  END
Download

3D SDF for NP0315580 (8-acetyl-7-hydroxychromen-2-one)


  Mrv1652309112216172D          

 15 16  0  0  0  0            999 V2000
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  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
 10 11  2  0  0  0  0
 11 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
  4 15  2  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C2OC(=O)C=CC2=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O4/c1-6(12)10-8(13)4-2-7-3-5-9(14)15-11(7)10/h2-5,13H,1H3

> <INCHI_KEY>
XWYMACPLPPQCHC-UHFFFAOYSA-N

> <FORMULA>
C11H8O4

> <MOLECULAR_WEIGHT>
204.181

> <EXACT_MASS>
204.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.388198704685987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-acetyl-7-hydroxy-2H-chromen-2-one

> <JCHEM_LOGP>
1.6874418123333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.775795484861842

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.605401770202847

> <JCHEM_PKA_STRONGEST_BASIC>
-6.433934327291769

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
53.932300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-acetyl-7-hydroxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0315580 (8-acetyl-7-hydroxychromen-2-one)

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PDB for NP0315580 (8-acetyl-7-hydroxychromen-2-one)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    4    9                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0315580 (8-acetyl-7-hydroxychromen-2-one)
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SMILES for NP0315580 (8-acetyl-7-hydroxychromen-2-one)
CC(=O)C1=C2OC(=O)C=CC2=CC=C1O
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INCHI for NP0315580 (8-acetyl-7-hydroxychromen-2-one)
InChI=1S/C11H8O4/c1-6(12)10-8(13)4-2-7-3-5-9(14)15-11(7)10/h2-5,13H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H8O4
Average Mass204.1810 Da
Monoisotopic Mass204.04226 Da
IUPAC Name8-acetyl-7-hydroxy-2H-chromen-2-one
Traditional Name8-acetyl-7-hydroxychromen-2-one
CAS Registry NumberNot Available
SMILES
CC(=O)C1=C2OC(=O)C=CC2=CC=C1O
InChI Identifier
InChI=1S/C11H8O4/c1-6(12)10-8(13)4-2-7-3-5-9(14)15-11(7)10/h2-5,13H,1H3
InChI KeyXWYMACPLPPQCHC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassHydroxycoumarins  
Direct Parent7-hydroxycoumarins  
Alternative Parents
Substituents
  • 7-hydroxycoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Acetophenone
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP1.69ChemAxon
pKa (Strongest Acidic)7.61ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity53.93 m³·mol⁻¹ChemAxon
Polarizability19.39 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4549513  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5411574  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sharma A, Nuthakki VK, Gairola S, Singh B, Bharate SB: A Coumarin-Donepezil Hybrid as a Blood-Brain Barrier Permeable Dual Cholinesterase Inhibitor: Isolation, Synthetic Modifications, and Biological Evaluation of Natural Coumarins. ChemMedChem. 2022 Sep 16;17(18):e202200300. doi: 10.1002/cmdc.202200300. Epub 2022 Aug 16. [PubMed:35892288  ] 
  2. Li D, Ji B, Sun H: Probing the binding of 8-Acetyl-7-hydroxycoumarin to human serum albumin by spectroscopic methods and molecular modeling. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Jul;73(1):35-40. doi: 10.1016/j.saa.2009.01.023. Epub 2009 Jan 31. [PubMed:19243988  ] 
  3. Cespedes CL, Avila JG, Martinez A, Serrato B, Calderon-Mugica JC, Salgado-Garciglia R: Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). J Agric Food Chem. 2006 May 17;54(10):3521-7. doi: 10.1021/jf053071w. [PubMed:19127719  ] 
  4. LOTUS database [Link]