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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:31:07 UTC

Update Date

2022-03-07 02:53:50 UTC

HMDB ID

HMDB0033757

Secondary Accession Numbers

HMDB33757

Metabolite Identification

Common Name

Marcanine A

Description

Marcanine A, also known as griffiazanone b, belongs to the class of organic compounds known as benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. Marcanine A has been detected, but not quantified in, alcoholic beverages and fruits. This could make marcanine a a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Marcanine A.

Structure

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


  Mrv0541 02241219492D          

 18 20  0  0  0  0            999 V2000
   -1.0685    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710   -0.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548   -1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984   -0.8243    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
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  2  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6 15  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  2  0  0  0  0
 13 14  2  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033757

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)NC2=C1C(=O)C1=C(C=CC=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H9NO3/c1-7-6-10(16)15-12-11(7)13(17)8-4-2-3-5-9(8)14(12)18/h2-6H,1H3,(H,15,16)

> <INCHI_KEY>
GYAHTYNHCVTZOK-UHFFFAOYSA-N

> <FORMULA>
C14H9NO3

> <MOLECULAR_WEIGHT>
239.2262

> <EXACT_MASS>
239.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.81088948319337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methyl-1H,2H,5H,10H-benzo[g]quinoline-2,5,10-trione

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
0.8581358246666666

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.421553528900565

> <JCHEM_PKA_STRONGEST_BASIC>
-4.797859269876697

> <JCHEM_POLAR_SURFACE_AREA>
63.24

> <JCHEM_REFRACTIVITY>
67.208

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
marcanin A

> <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      -1.995   0.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.995  -0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.662  -1.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -0.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.667   0.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.662   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.329   1.541   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.664   0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.664  -0.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.329  -1.539   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.999  -1.539   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.329  -0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.329   0.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.999   1.539   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.662   3.079   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.662  -3.079   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.999   3.079   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.664  -1.539   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   14                                                  
CONECT    6    1    5   15                                                  
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    2    9                                                       
CONECT   11    4   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14    5   13   17                                                  
CONECT   15    6                                                            
CONECT   16    3                                                            
CONECT   17   14                                                            
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0033757
HETATM    1  C1  UNL     1      -2.398   2.247   0.638  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.264   0.872   0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.370   0.132  -0.287  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.152  -1.141  -0.763  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.192  -1.784  -1.119  1.00  0.00           O  
HETATM    6  N1  UNL     1      -1.947  -1.715  -0.867  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.861  -1.024  -0.488  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.033   0.253  -0.005  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.167   0.982   0.400  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.074   2.169   0.856  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.470   0.337   0.279  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.601   1.031   0.664  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.854   0.464   0.568  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.035  -0.815   0.085  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.888  -1.496  -0.296  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.633  -0.936  -0.203  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.433  -1.678  -0.614  1.00  0.00           C  
HETATM   18  O3  UNL     1       0.579  -2.843  -1.055  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.494   2.498   0.621  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.103   2.277   1.688  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.924   3.014  -0.005  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.360   0.573  -0.214  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.856  -2.703  -1.245  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.461   2.044   1.046  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.724   1.009   0.868  1.00  0.00           H  
HETATM   26  H8  UNL     1       5.023  -1.262   0.009  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.012  -2.500  -0.677  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    8
CONECT    3    4   22
CONECT    4    5    5    6
CONECT    6    7   23
CONECT    7    8    8   17
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
CONECT   16   17
CONECT   17   18   18
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Griffiazanone b	MeSH
4-Methyl-1H-1-aza-2,9,10-anthracenetrione	HMDB
4-methylbenzo[g]Quinoline-2,5,10(1H)-trione, 9ci	HMDB
Marcanine a	MeSH

Chemical Formula

C₁₄H₉NO₃

Average Molecular Weight

239.2262

Monoisotopic Molecular Weight

239.058243159

IUPAC Name

4-methyl-1H,2H,5H,10H-benzo[g]quinoline-2,5,10-trione

Traditional Name

marcanin A

CAS Registry Number

157463-84-8

SMILES

CC1=CC(=O)NC2=C1C(=O)C1=C(C=CC=C1)C2=O

InChI Identifier

InChI=1S/C14H9NO3/c1-7-6-10(16)15-12-11(7)13(17)8-4-2-3-5-9(8)14(12)18/h2-6H,1H3,(H,15,16)

InChI Key

GYAHTYNHCVTZOK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Benzoquinolines

Alternative Parents

Substituents

Benzoquinoline
Quinoline quinone
Naphthalene
Aryl ketone
Methylpyridine
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Ketone
Lactam
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
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

Extracellular (HMDB: HMDB0033757)
Cytoplasm (HMDB: HMDB0033757)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033757)

Source

Exogenous

Food

Food (HMDB: HMDB0033757)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0033757)

Not Available

Nutrient (HMDB: HMDB0033757)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	249 - 251 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	1.78	ALOGPS
logP	0.86	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.24 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.21 m³·mol⁻¹	ChemAxon
Polarizability	23.81 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.053	31661259
DarkChem	[M-H]-	153.222	31661259
DeepCCS	[M+H]+	154.331	30932474
DeepCCS	[M-H]-	151.973	30932474
DeepCCS	[M-2H]-	184.912	30932474
DeepCCS	[M+Na]+	160.424	30932474
AllCCS	[M+H]+	151.4	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	155.2	32859911
AllCCS	[M+Na]+	156.3	32859911
AllCCS	[M-H]-	154.7	32859911
AllCCS	[M+Na-2H]-	153.9	32859911
AllCCS	[M+HCOO]-	153.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Marcanine A	CC1=CC(=O)NC2=C1C(=O)C1=C(C=CC=C1)C2=O	3017.5	Standard polar	33892256
Marcanine A	CC1=CC(=O)NC2=C1C(=O)C1=C(C=CC=C1)C2=O	2127.2	Standard non polar	33892256
Marcanine A	CC1=CC(=O)NC2=C1C(=O)C1=C(C=CC=C1)C2=O	2615.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Marcanine A,1TMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C)C2=C1C(=O)C1=CC=CC=C1C2=O	2426.4	Semi standard non polar	33892256
Marcanine A,1TMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C)C2=C1C(=O)C1=CC=CC=C1C2=O	2372.2	Standard non polar	33892256
Marcanine A,1TBDMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)C1=CC=CC=C1C2=O	2613.6	Semi standard non polar	33892256
Marcanine A,1TBDMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)C1=CC=CC=C1C2=O	2574.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Marcanine A GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p9-1980000000-9ac6b281dab43cf05a7d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Marcanine A 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 - Marcanine A 10V, Positive-QTOF	splash10-0006-0090000000-a972810102c1214918a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 20V, Positive-QTOF	splash10-0006-0390000000-2b51265f3ec8bcc1ebeb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 40V, Positive-QTOF	splash10-0pi9-5930000000-45c4899a3c4498110060	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 10V, Negative-QTOF	splash10-000i-0090000000-e17ad508c39e20b27a2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 20V, Negative-QTOF	splash10-000i-0090000000-f7f6843d6a883f0626a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 40V, Negative-QTOF	splash10-00ej-5980000000-80cd6c86544d798fbb2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 10V, Positive-QTOF	splash10-0006-0090000000-9fa7debb10e1f3436126	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 20V, Positive-QTOF	splash10-0006-0090000000-f5e1477749b003df9c53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 40V, Positive-QTOF	splash10-0r0s-3930000000-3c35b44aeb6addc3a864	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 10V, Negative-QTOF	splash10-000i-0090000000-f79f832e3721a47c5ba2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 20V, Negative-QTOF	splash10-000i-0090000000-f79f832e3721a47c5ba2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Marcanine A 40V, Negative-QTOF	splash10-007a-0590000000-d153029c5429f8e0191f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB011892

KNApSAcK ID

C00028313

Chemspider ID

8281180

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10105653

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Marcanine A (HMDB0033757)

MOL for HMDB0033757 (Marcanine A)

3D MOL for HMDB0033757 (Marcanine A)

3D SDF for HMDB0033757 (Marcanine A)

3D-SDF for HMDB0033757 (Marcanine A)

PDB for HMDB0033757 (Marcanine A)

3D PDB for HMDB0033757 (Marcanine A)

SMILES for HMDB0033757 (Marcanine A)

INCHI for HMDB0033757 (Marcanine A)

Structure for HMDB0033757 (Marcanine A)

3D Structure for HMDB0033757 (Marcanine A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra