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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:10 UTC

Update Date

2023-02-21 17:22:57 UTC

HMDB ID

HMDB0033000

Secondary Accession Numbers

HMDB33000

Metabolite Identification

Common Name

10-Methylacridone

Description

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. 10-Methylacridone has been detected, but not quantified in, citrus. This could make 10-methylacridone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 10-Methylacridone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 05061306512D          

 16 18  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    3.5724    1.2375    0.0000 C   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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033000

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO/c1-15-12-8-4-2-6-10(12)14(16)11-7-3-5-9-13(11)15/h2-9H,1H3

> <INCHI_KEY>
XUVKSPPGPPFPQN-UHFFFAOYSA-N

> <FORMULA>
C14H11NO

> <MOLECULAR_WEIGHT>
209.2432

> <EXACT_MASS>
209.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.741302818825268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.122954878333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.18964909881743686

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
63.95840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2    4    6                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   12   14                                                  
CONECT   11    7   13   14                                                  
CONECT   12    8   10   15                                                  
CONECT   13    9   11   15                                                  
CONECT   14   10   11   16                                                  
CONECT   15    1   12   13                                                  
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0033000
HETATM    1  C1  UNL     1       0.153   2.434   0.189  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.020   1.038   0.074  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.128   0.287   0.030  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.369   0.890   0.087  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.551   0.145   0.042  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.536  -1.221  -0.061  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.304  -1.825  -0.118  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.112  -1.087  -0.074  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.088  -1.753  -0.138  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.113  -3.008  -0.233  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.246  -1.010  -0.095  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.487  -1.608  -0.156  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.661  -0.892  -0.117  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.607   0.475  -0.013  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.346   1.093   0.049  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.183   0.375   0.011  1.00  0.00           C  
HETATM   17  H1  UNL     1       0.798   2.771  -0.676  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.667   3.095   0.381  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.808   2.604   1.103  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.409   1.965   0.166  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.483   0.678   0.091  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.464  -1.773  -0.093  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.266  -2.896  -0.199  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.536  -2.684  -0.238  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.638  -1.352  -0.164  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.487   1.111   0.023  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.302   2.149   0.127  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   16
CONECT    3    4    4    8
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   15   26
CONECT   15   16   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-Methyl-9(10H)-acridinone	HMDB
10-Methyl-9(10H)-acridinone, 9ci	HMDB
10-Methyl-9(10H)-acridone	HMDB
10-Methyl-9-acridanone	HMDB
10-Methyl-9-acridanone, 8ci	HMDB
10-Methylacridin-9(10H)-one	HMDB
10-Methylacridon	HMDB
9(10H)-Acridinone, 10-methyl- (9ci)	HMDB
9-Acridanone, 10-methyl- (8ci)	HMDB
N-Methyl-9-acridone	HMDB
N-Methyl-acridone	HMDB
N-Methylacridone	HMDB

Chemical Formula

C₁₄H₁₁NO

Average Molecular Weight

209.2432

Monoisotopic Molecular Weight

209.084063979

IUPAC Name

10-methyl-9,10-dihydroacridin-9-one

Traditional Name

10-methylacridin-9-one

CAS Registry Number

719-54-0

SMILES

CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C14H11NO/c1-15-12-8-4-2-6-10(12)14(16)11-7-3-5-9-13(11)15/h2-9H,1H3

InChI Key

XUVKSPPGPPFPQN-UHFFFAOYSA-N

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
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033000)
Cell membrane (HMDB: HMDB0033000)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033000)

Source

Exogenous

Exogenous (HMDB: HMDB0033000)

Food

Food (HMDB: HMDB0033000)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0033000)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033000)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199 - 200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	37.75 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.6 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.12	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	0.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.96 m³·mol⁻¹	ChemAxon
Polarizability	22.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	147.002	31661259
DarkChem	[M-H]-	146.77	31661259
DeepCCS	[M-2H]-	172.309	30932474
DeepCCS	[M+Na]+	146.768	30932474
AllCCS	[M+H]+	143.6	32859911
AllCCS	[M+H-H2O]+	139.1	32859911
AllCCS	[M+NH4]+	147.7	32859911
AllCCS	[M+Na]+	148.9	32859911
AllCCS	[M-H]-	148.4	32859911
AllCCS	[M+Na-2H]-	147.8	32859911
AllCCS	[M+HCOO]-	147.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
10-Methylacridone	CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12	2851.4	Standard polar	33892256
10-Methylacridone	CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12	2017.5	Standard non polar	33892256
10-Methylacridone	CN1C2=CC=CC=C2C(=O)C2=CC=CC=C12	2488.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Methylacridone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-0960000000-4bccaf932e0e07077d9b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Methylacridone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 10V, Negative-QTOF	splash10-0a4i-0090000000-1351596cb53dc3547c61	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 20V, Negative-QTOF	splash10-0a4i-0090000000-2abad9b5b9114d84ec55	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 40V, Negative-QTOF	splash10-052f-1940000000-024b5a1f2fb72f77e724	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 10V, Negative-QTOF	splash10-0a4i-0090000000-9f12ac38c8faae87e87f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 20V, Negative-QTOF	splash10-0a4i-0090000000-9f12ac38c8faae87e87f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 40V, Negative-QTOF	splash10-0a4i-0390000000-fb11d194eb7deea2fb64	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 10V, Positive-QTOF	splash10-03di-0090000000-8cc4e9131b8005596fb1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 20V, Positive-QTOF	splash10-03di-0090000000-ad6dfbcd1d555fdba260	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 40V, Positive-QTOF	splash10-0lyo-2920000000-260d77ef86d134b4cd62	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 10V, Positive-QTOF	splash10-03di-0090000000-c353998d16bfd154b10e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 20V, Positive-QTOF	splash10-03di-0090000000-c353998d16bfd154b10e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Methylacridone 40V, Positive-QTOF	splash10-0a6r-4950000000-0ffe448453543fa835a5	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010989

KNApSAcK ID

C00052396

Chemspider ID

62950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69751

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1157071

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 10-Methylacridone (HMDB0033000)

MOL for HMDB0033000 (10-Methylacridone)

3D MOL for HMDB0033000 (10-Methylacridone)

3D SDF for HMDB0033000 (10-Methylacridone)

3D-SDF for HMDB0033000 (10-Methylacridone)

PDB for HMDB0033000 (10-Methylacridone)

3D PDB for HMDB0033000 (10-Methylacridone)

SMILES for HMDB0033000 (10-Methylacridone)

INCHI for HMDB0033000 (10-Methylacridone)

Structure for HMDB0033000 (10-Methylacridone)

3D Structure for HMDB0033000 (10-Methylacridone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra