NP-MRD: Showing NP-Card for 2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one (NP0083545)

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Record Information

Version

2.0

Created at

2022-04-29 04:33:23 UTC

Updated at

2022-04-29 04:33:23 UTC

NP-MRD ID

NP0083545

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one

Description

Hallacridone belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Hallacridone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Hallacridone has been detected, but not quantified in, herbs and spices. 2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one is found in Ruta bracteosa, Ruta callus cultures, Ruta chalepensis , Ruta graveolens , Ruta macrophylla and Thamnosma montana. This could make hallacridone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    5.0308   -1.3025    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623   -0.1530   -0.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225    0.4225   -1.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.3032   -0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794   -0.2825   -0.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018    0.4350   -0.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6980    1.4371   -1.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8321    2.3214   -1.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5131    2.2410   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3981    3.1384   -2.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183    1.2691   -0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    1.2436   -0.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258    2.0919   -1.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722    0.2956    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2385    0.3222    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600   -0.6115    1.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -1.5110    1.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611   -1.5155    1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -0.5965    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.5855    0.5374 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544   -1.6198    1.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1731    0.3535   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0008    1.2980   -1.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645   -1.4633    1.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9801   -1.0825    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1824   -2.2204   -0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3505   -1.0852    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340    3.0907   -2.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262    3.8702   -2.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9062    1.0224   -0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8378   -0.6009    1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708   -2.2439    2.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9920   -2.2646    2.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5542   -2.4754    1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6519   -1.3757    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202   -2.1662    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 22  2  0
 22  6  1  0
  6  7  2  0
  7 23  1  0
 23  4  1  0
  4  5  2  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 22 20  1  0
  5  6  1  0
 18 19  1  0
  9 11  1  0
 21 34  1  0
 21 35  1  0
 21 36  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
  5 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  8 28  1  0
 10 29  1  0
M  END


  Mrv0541 02241219302D          

 23 26  0  0  0  0            999 V2000
   -2.4508   -1.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335   -2.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -1.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252   -0.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0426   -0.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6143   -1.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0818   -2.5732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -1.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -1.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -0.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162    0.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162    0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5522    1.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970    2.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066    2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066   -2.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -1.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5522   -0.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418    0.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5714   -0.1228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170    0.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143    2.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 21  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 23  2  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  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083545

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(C=CC=C2)C(=O)C2=C1C1=C(OC(=C1)C(C)=O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO4/c1-9(20)14-7-11-15(23-14)8-13(21)16-17(11)19(2)12-6-4-3-5-10(12)18(16)22/h3-8,21H,1-2H3

> <INCHI_KEY>
GZVRDNACRGJZNW-UHFFFAOYSA-N

> <FORMULA>
C18H13NO4

> <MOLECULAR_WEIGHT>
307.3001

> <EXACT_MASS>
307.084457909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.08199496707556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-acetyl-5-hydroxy-11-methyl-6H,11H-furo[2,3-c]acridin-6-one

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
3.106161599666666

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.6065342470121

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.1390649935259

> <JCHEM_PKA_STRONGEST_BASIC>
-1.946142547630357

> <JCHEM_POLAR_SURFACE_AREA>
70.75

> <JCHEM_REFRACTIVITY>
85.06070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.575  -3.431   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.049  -3.888   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.982  -2.821   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.287  -1.297   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.813  -0.838   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.880  -1.905   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.153  -4.803   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.458  -3.279   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.610  -2.211   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.306  -0.686   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.524   0.228   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.524   1.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.897   2.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.354   3.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.439   4.803   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.439  -4.193   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.134  -2.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.202  -1.754   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.897  -0.229   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.811   0.990   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      -1.067  -0.229   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -1.525   1.143   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.880   4.041   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    8                                                            
CONECT    8    3    7    9                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17    9   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   11   18   20                                                  
CONECT   20   13   19                                                       
CONECT   21    4   10   22                                                  
CONECT   22   21                                                            
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one, 9ci	HMDB

Chemical Formula

C₁₈H₁₃NO₄

Average Mass

307.3001 Da

Monoisotopic Mass

307.08446 Da

IUPAC Name

2-acetyl-5-hydroxy-11-methyl-6H,11H-furo[2,3-c]acridin-6-one

Traditional Name

2-acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6-one

CAS Registry Number

Not Available

SMILES

CN1C2=C(C=CC=C2)C(=O)C2=C1C1=C(OC(=C1)C(C)=O)C=C2O

InChI Identifier

InChI=1S/C18H13NO4/c1-9(20)14-7-11-15(23-14)8-13(21)16-17(11)19(2)12-6-4-3-5-10(12)18(16)22/h3-8,21H,1-2H3

InChI Key

GZVRDNACRGJZNW-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
Ruta bracteosa	Plant	KNApSAcK
Ruta callus cultures	Plant	KNApSAcK
Ruta chalepensis	Plant	KNApSAcK
Ruta graveolens	Plant	KNApSAcK
Ruta macrophylla	Plant	KNApSAcK
Thamnosma montana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Dihydroquinolone
Dihydroquinoline
Benzofuran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Furan
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Ketone
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.21	ALOGPS
logP	3.11	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.06 m³·mol⁻¹	ChemAxon
Polarizability	32.08 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

HMDB0029826

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001038

KNApSAcK ID

Not Available

Chemspider ID

30776794

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14380428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one (NP0083545)

MOL for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

3D MOL for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

3D SDF for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

3D-SDF for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

PDB for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

3D PDB for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

SMILES for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

INCHI for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

Structure for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)

3D Structure for NP0083545 (2-Acetyl-5-hydroxy-11-methylfuro[2,3-c]acridin-6(11H)-one)