NP-MRD: Showing NP-Card for Casimiroin (NP0051206)

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Record Information

Version

2.0

Created at

2022-04-27 22:36:36 UTC

Updated at

2022-04-27 22:36:36 UTC

NP-MRD ID

NP0051206

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Casimiroin

Description

Casimiroin belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Casimiroin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Casimiroin has been detected, but not quantified in, pomes. Casimiroin is found in Casimiroa edulis , Casimiroa pubescena and Dictyoloma vandellianum. This could make casimiroin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

XM5
  Mrv0541 02241214172D          

 17 19  0  0  0  0            999 V2000
   -1.7845    1.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499    1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253    1.0277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    1.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907    0.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339    0.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1685   -0.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9697   -0.1524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303    0.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    0.9822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -1.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461   -1.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3053   -0.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399    0.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6953   -1.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607   -1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  5  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  2  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051206

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)N(C)C2=C1C=CC1=C2OCO1

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO4/c1-13-10(14)5-9(15-2)7-3-4-8-12(11(7)13)17-6-16-8/h3-5H,6H2,1-2H3

> <INCHI_KEY>
DPXXJCMMMXZVSW-UHFFFAOYSA-N

> <FORMULA>
C12H11NO4

> <MOLECULAR_WEIGHT>
233.22

> <EXACT_MASS>
233.068807845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.030425343517866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methoxy-9-methyl-2H,8H,9H-[1,3]dioxolo[4,5-h]quinolin-8-one

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
0.44372236833333356

> <ALOGPS_LOGS>
-1.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9387374816841167

> <JCHEM_POLAR_SURFACE_AREA>
48

> <JCHEM_REFRACTIVITY>
60.8055

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
casimiroin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: XM5                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -3.331   3.179   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.520   1.870   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.981   1.918   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.253   3.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.169   0.609   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.370   0.657   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.181  -0.652   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.677  -0.284   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.790   1.251   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.364   1.833   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.453  -2.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.086  -2.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.897  -0.748   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.437  -0.796   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.248   0.513   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.165  -2.153   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.353  -3.462   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    6    9                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13    5   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15    2   14                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
4-Methoxy-1-methyl-7,8-methylenedioxy-2(1H)-quinolinone	HMDB
6-Methoxy-9-methyl-1,3-dioxolo(4,5-H)quinolin-8(9H)-one	HMDB
6-Methoxy-9-methyl-1,3-dioxolo[4,5-H]quinolin-8(9H)-one, 9ci	HMDB
6-Methoxy-9-methyl-(1,3)dioxolo(4,5-H)quinolin-8(9H)-one	HMDB

Chemical Formula

C₁₂H₁₁NO₄

Average Mass

233.2200 Da

Monoisotopic Mass

233.06881 Da

IUPAC Name

6-methoxy-9-methyl-2H,8H,9H-[1,3]dioxolo[4,5-h]quinolin-8-one

Traditional Name

casimiroin

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)N(C)C2=C1C=CC1=C2OCO1

InChI Identifier

InChI=1S/C12H11NO4/c1-13-10(14)5-9(15-2)7-3-4-8-12(11(7)13)17-6-16-8/h3-5H,6H2,1-2H3

InChI Key

DPXXJCMMMXZVSW-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
Casimiroa edulis	Plant	KNApSAcK
Casimiroa pubescena	Plant	KNApSAcK
Dictyoloma vandellianum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Dihydroquinoline
Benzodioxole
Alkyl aryl ether
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactam
Ether
Oxacycle
Azacycle
Acetal
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:3452 )
Quinoline alkaloids (C10654 )

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	1.34	ALOGPS
logP	0.44	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.81 m³·mol⁻¹	ChemAxon
Polarizability	23.03 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