NP-MRD: Showing NP-Card for 1-Hydroxy-3-methoxy-N-methylacridone (NP0066627)

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Record Information

Version

2.0

Created at

2022-04-28 10:51:30 UTC

Updated at

2022-04-28 10:51:30 UTC

NP-MRD ID

NP0066627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Hydroxy-3-methoxy-N-methylacridone

Description

1-Hydroxy-3-methoxy-10-methylacridone 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. 1-Hydroxy-3-methoxy-10-methylacridone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1-Hydroxy-3-methoxy-10-methylacridone has been detected, but not quantified in, herbs and spices. 1-Hydroxy-3-methoxy-N-methylacridone is found in Citrus maxima, Esenbeckia febrifuga, Fagara macrophylla , Glycosmis pentaphylla, Limonia acidissima, Ruta graveolens , Thamnosma montana, Zanthoxylum gilletii, Zanthoxylum leprieurii and Zanthoxylum rubescens. This could make 1-hydroxy-3-methoxy-10-methylacridone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.1835    0.3357   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9520    0.9889   -0.3120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303    0.3151   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7389   -1.0385   -0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4958   -1.7055   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421   -3.0588   -0.2879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223   -0.9813   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890   -1.6343   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9904   -2.8784   -0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -0.8651   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346   -1.5567   -0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175   -0.8548   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3696    0.5108   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1573    1.1922   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    0.4971   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587    1.1440   -0.1570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418    2.5724   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.4081   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697    1.0720   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9908    1.0187   -0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3439    0.0006   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2117   -0.5386    0.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291   -1.6447   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003   -3.7606   -0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2565   -2.6288   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3944   -1.3245   -0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    1.1077    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1306    2.2691   -0.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5087    2.8457   -1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0592    3.1458   -0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    2.9123    0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6177    2.1343   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 18  1  0
 18  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
  4  3  1  0
 15 10  1  0
 16 18  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 32  1  0
  6 24  1  0
  4 23  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
M  END


  Mrv0541 02241215582D          

 19 21  0  0  0  0            999 V2000
   -2.8586    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -0.8260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0021   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0021    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154    1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -1.6517    0.0000 C   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
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 14 16  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1N2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO3/c1-16-11-6-4-3-5-10(11)15(18)14-12(16)7-9(19-2)8-13(14)17/h3-8,17H,1-2H3

> <INCHI_KEY>
OCUBFJMZYYIVBO-UHFFFAOYSA-N

> <FORMULA>
C15H13NO3

> <MOLECULAR_WEIGHT>
255.2686

> <EXACT_MASS>
255.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.74770717597406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-3-methoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.311718290999999

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.041327265250542

> <JCHEM_PKA_STRONGEST_BASIC>
-1.42280750574405

> <JCHEM_POLAR_SURFACE_AREA>
49.77000000000001

> <JCHEM_REFRACTIVITY>
72.4025

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-3-methoxy-10-methylacridin-9-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      -5.336   0.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.002  -1.542   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.670  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.670   0.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.002   1.541   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.335  -1.542   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.004  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.004   0.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.335   1.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.330  -1.542   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.662  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.662   0.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.330   1.541   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.335   3.083   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.330   3.083   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.999  -1.542   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.335  -3.083   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   19                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    5    9   15                                                  
CONECT   11    8   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13   16                                                  
CONECT   15   10                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17                                                            
CONECT   19    7                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-Hydroxy-3-methoxy-10-methyl-9(10H)-acridinone	HMDB
1-Hydroxy-3-methoxy-10-methyl-9-acridanone	HMDB
1-Hydroxy-3-methoxy-N-methylacridone	HMDB
1-HMMA CPD	MeSH

Chemical Formula

C₁₅H₁₃NO₃

Average Mass

255.2686 Da

Monoisotopic Mass

255.08954 Da

IUPAC Name

1-hydroxy-3-methoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1-hydroxy-3-methoxy-10-methylacridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1N2C

InChI Identifier

InChI=1S/C15H13NO3/c1-16-11-6-4-3-5-10(11)15(18)14-12(16)7-9(19-2)8-13(14)17/h3-8,17H,1-2H3

InChI Key

OCUBFJMZYYIVBO-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
Citrus maxima	LOTUS Database	35616633
Esenbeckia febrifuga	LOTUS Database	35616633
Fagara macrophylla	Plant	KNApSAcK
Glycosmis pentaphylla	LOTUS Database	35616633
Limonia acidissima	LOTUS Database	35616633
Ruta graveolens	Plant	KNApSAcK
Thamnosma montana	LOTUS Database	35616633
Zanthoxylum gilletii	LOTUS Database	35616633
Zanthoxylum leprieurii	LOTUS Database	35616633
Zanthoxylum rubescens	LOTUS Database	35616633

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
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Ether
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen 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	2.74	ALOGPS
logP	3.31	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.04	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.4 m³·mol⁻¹	ChemAxon
Polarizability	26.75 Å³	ChemAxon
Number of Rings	3	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

HMDB0029322

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000383

KNApSAcK ID

C00024230

Chemspider ID

4526466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5377412

PDB ID

Not Available

ChEBI ID

725388

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-Hydroxy-3-methoxy-N-methylacridone (NP0066627)

MOL for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

3D MOL for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

3D SDF for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

3D-SDF for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

PDB for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

3D PDB for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

SMILES for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

INCHI for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

Structure for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)

3D Structure for NP0066627 (1-Hydroxy-3-methoxy-N-methylacridone)