NP-MRD: Showing NP-Card for Griffiazanone B (NP0069916)

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Record Information

Version

2.0

Created at

2022-04-28 15:13:11 UTC

Updated at

2022-04-28 15:13:11 UTC

NP-MRD ID

NP0069916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Griffiazanone B

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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Marcanine A has been detected, but not quantified in, alcoholic beverages and fruits. Griffiazanone B is found in Annona glabra , Goniothalamus griffithii, Goniothalamus laoticus and Goniothalamus tamirensis. This could make marcanine a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 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>
NP0069916

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

Synonyms

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

Chemical Formula

C₁₄H₉NO₃

Average Mass

239.2262 Da

Monoisotopic Mass

239.05824 Da

IUPAC Name

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

Traditional Name

marcanin A

CAS Registry Number

Not Available

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

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
Annona glabra	Plant	KNApSAcK
Goniothalamus griffithii	Plant	KNApSAcK
Goniothalamus laoticus	LOTUS Database	35616633
Goniothalamus tamirensis	LOTUS Database	35616633

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

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	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

External Links

HMDB ID

HMDB0033757

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Griffiazanone B (NP0069916)

MOL for NP0069916 (Griffiazanone B)

3D MOL for NP0069916 (Griffiazanone B)

3D SDF for NP0069916 (Griffiazanone B)

3D-SDF for NP0069916 (Griffiazanone B)

PDB for NP0069916 (Griffiazanone B)

3D PDB for NP0069916 (Griffiazanone B)

SMILES for NP0069916 (Griffiazanone B)

INCHI for NP0069916 (Griffiazanone B)

Structure for NP0069916 (Griffiazanone B)

3D Structure for NP0069916 (Griffiazanone B)