NP-MRD: Showing NP-Card for Rutalinium (NP0083615)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 04:36:03 UTC

Updated at

2022-04-29 04:36:03 UTC

NP-MRD ID

NP0083615

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rutalinium

Description

Rutalinium belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Rutalinium is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Rutalinium has been detected, but not quantified in, herbs and spices. Rutalinium is found in Ruta graveolens and Ruta graveolens ssp.hortensis . This could make rutalinium a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    1.5478    3.2730    0.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104    2.0734    1.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    0.8565    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    0.5173    0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -0.6928   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4169   -1.5141   -0.4707 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.0573   -2.7868   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134   -1.1681   -0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045   -2.0248   -0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -1.6537   -0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205   -0.4426   -0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -0.1084   -0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4142    0.3747    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0823    0.0422    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8926   -1.0817   -0.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982   -0.1186   -0.0956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9860    0.5565   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2185   -0.8494    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6929    0.9237    0.9751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0663    0.3712    2.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084    1.4371    1.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918    3.4111    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368    3.4051   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432    4.1197    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155   -2.9253   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0325   -2.8740   -1.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -3.5850   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046   -2.9601   -1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079   -2.3030   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961   -0.3817    0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    1.3166    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    0.7407   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130    1.5272   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5402   -0.1450   -2.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9542   -0.0970    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5575   -1.3595   -0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019   -1.6032    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840    1.7751    0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366   -0.1431    2.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1027    1.6842    2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1699    2.4125    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 14  2  0
 14 13  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  4 21  1  0
 21 19  1  0
 19 20  1  0
 19 16  1  0
 16 17  1  6
 16 18  1  0
 16 15  1  0
  4  3  1  0
  8 14  1  0
 15  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 31  1  0
 12 30  1  0
 10 29  1  0
  9 28  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 21 40  1  0
 21 41  1  0
 19 38  1  6
 20 39  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  1   6   1
M  END


  Mrv0541 04041306412D          

 21 23  0  0  0  0            999 V2000
    5.2643   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -3.2411    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5498   -4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2643   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788   -4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8354   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8354   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -5.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2643   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788   -1.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2643   -2.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6932   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6932   -2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4077   -1.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6932   -4.4786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4077   -4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -6.5411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8353   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788   -0.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2643   -1.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
 10  4  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  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
  6 13  1  0  0  0  0
  1  6  2  0  0  0  0
 12  1  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 18  1  0  0  0  0
  2 19  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
NP0083615

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=C(O)C=CC2=[N+](C)C2=C1CC(O)C(C)(C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO4/c1-16(2)13(19)8-11-14(20-4)10-7-9(18)5-6-12(10)17(3)15(11)21-16/h5-7,13,19H,8H2,1-4H3/p+1

> <INCHI_KEY>
YNZXAOOXQYAYLT-UHFFFAOYSA-O

> <FORMULA>
C16H20NO4

> <MOLECULAR_WEIGHT>
290.3343

> <EXACT_MASS>
290.139233133

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.331589153167503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7-dihydroxy-5-methoxy-2,2,10-trimethyl-2H,3H,4H-pyrano[2,3-b]quinolin-10-ium

> <ALOGPS_LOGP>
-1.06

> <JCHEM_LOGP>
-2.591828677471745

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.647675062477042

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9044864785300275

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3939925532175694

> <JCHEM_POLAR_SURFACE_AREA>
62.80000000000001

> <JCHEM_REFRACTIVITY>
78.87390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dihydroxy-5-methoxy-2,2,10-trimethyl-3H,4H-pyrano[2,3-b]quinolin-10-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-APR-13         0                                  
HETATM    1  C   UNK     0       9.827  -5.280   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       8.493  -6.050   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       8.493  -7.590   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.827  -8.360   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.160  -7.590   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.160  -6.050   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.159  -8.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.159  -9.900   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.493 -10.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.827  -9.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.160  -2.970   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.827  -3.740   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.494  -5.280   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.494  -3.740   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.828  -2.970   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.494  -8.360   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.828  -7.590   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.493 -12.210   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.159  -5.280   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.160  -1.430   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.827  -2.200   0.000  0.00  0.00           C+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4    7                                                  
CONECT    4    5   10    3                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5   13    1                                                  
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    4    9                                                       
CONECT   11   12   14   20   21                                             
CONECT   12    1   11                                                       
CONECT   13    6   14                                                       
CONECT   14   13   11   15                                                  
CONECT   15   14                                                            
CONECT   16    5   17                                                       
CONECT   17   16                                                            
CONECT   18    9                                                            
CONECT   19    2                                                            
CONECT   20   11                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀NO₄

Average Mass

290.3343 Da

Monoisotopic Mass

290.13923 Da

IUPAC Name

3,7-dihydroxy-5-methoxy-2,2,10-trimethyl-2H,3H,4H-pyrano[2,3-b]quinolin-10-ium

Traditional Name

3,7-dihydroxy-5-methoxy-2,2,10-trimethyl-3H,4H-pyrano[2,3-b]quinolin-10-ium

CAS Registry Number

Not Available

SMILES

COC1=C2C=C(O)C=CC2=[N+](C)C2=C1CC(O)C(C)(C)O2

InChI Identifier

InChI=1S/C16H19NO4/c1-16(2)13(19)8-11-14(20-4)10-7-9(18)5-6-12(10)17(3)15(11)21-16/h5-7,13,19H,8H2,1-4H3/p+1

InChI Key

YNZXAOOXQYAYLT-UHFFFAOYSA-O

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
Ruta graveolens	Plant	KNApSAcK
Ruta graveolens ssp.hortensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Hydroxyquinoline
Pyranopyridine
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Pyridine
Benzenoid
Pyridinium
Heteroaromatic compound
Secondary alcohol
Ether
Oxacycle
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organic cation
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	-1.1	ALOGPS
logP	-2.6	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.9	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.87 m³·mol⁻¹	ChemAxon
Polarizability	31.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033348

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011376

KNApSAcK ID

Not Available

Chemspider ID

153689

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176456

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rutalinium (NP0083615)

MOL for NP0083615 (Rutalinium)

3D MOL for NP0083615 (Rutalinium)

3D SDF for NP0083615 (Rutalinium)

3D-SDF for NP0083615 (Rutalinium)

PDB for NP0083615 (Rutalinium)

3D PDB for NP0083615 (Rutalinium)

SMILES for NP0083615 (Rutalinium)

INCHI for NP0083615 (Rutalinium)

Structure for NP0083615 (Rutalinium)

3D Structure for NP0083615 (Rutalinium)