NP-MRD: Showing NP-Card for (-)-Tabouensinium chloride (NP0083390)

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Record Information

Version

2.0

Created at

2022-04-29 04:27:19 UTC

Updated at

2022-04-29 04:27:19 UTC

NP-MRD ID

NP0083390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Tabouensinium chloride

Description

(3S)-3-hydroxy-5-methoxy-2,2,10-trimethyl-2H,3H,4H,10H-1λ⁴-pyrano[2,3-b]quinolin-1-ylium chloride 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. (-)-Tabouensinium chloride is found in Araliopsis tabouensis. Based on a literature review very few articles have been published on (3S)-3-hydroxy-5-methoxy-2,2,10-trimethyl-2H,3H,4H,10H-1λ⁴-pyrano[2,3-b]quinolin-1-ylium chloride.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    1.9768    3.1754    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7434    2.2148   -0.5772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3429    0.9104   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    0.6655   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -0.6579   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5462   -1.6203    0.1593 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.1408   -3.0034    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -1.3687    0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -2.3557    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1859   -2.1148    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948   -0.8206   -0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6563    0.1790   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2991   -0.0667   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229   -1.0111    0.0524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563   -0.0430   -0.0165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0116   -0.6545   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119    0.4483    1.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2991    1.0414   -0.9545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3139    1.9569   -1.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    1.7249   -0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0 15  0  0  0  0  0  0
    2.7695    3.8642    0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828    3.8435    0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    2.7714    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984   -3.4088    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231   -3.6213   -0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9727   -3.0133    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617   -3.3567    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214   -2.9174    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6612   -0.6433   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674    1.1914   -0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9595   -1.7627   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9047   -0.2727   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1496   -0.3365   -1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032    0.3549    1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982   -0.1670    2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7080    1.4905    1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458    0.5492   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4595    2.0766   -2.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7418    2.4381   -1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2011    2.3201    0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4 20  1  0
 20 18  1  0
 18 19  1  0
 18 15  1  0
 15 16  1  6
 15 17  1  0
 15 14  1  0
 14  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 13  3  1  0
  5  4  1  0
  9  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 20 40  1  0
 20 41  1  0
 18 38  1  6
 19 39  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 12 31  1  0
 11 30  1  0
 10 29  1  0
  9 28  1  0
M  CHG  2   6   1  21  -1
M  END


  Mrv1652304292206272D          

 21 22  0  0  1  0            999 V2000
   -1.0907   -1.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.5785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -0.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3382   -0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527   -0.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672   -0.3410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4816   -0.7535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672    0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796    0.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493    1.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    0.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3382    0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762    0.8965    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.0907    0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907   -0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8052   -0.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197   -0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197    0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8052    0.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762    1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9368    0.0000    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
M  CHG  2  13   1  21  -1
M  END
> <DATABASE_ID>
NP0083390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[Cl-].COC1=C2C[C@H](O)C(C)(C)OC2=[N+](C)C2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H20NO3.ClH/c1-16(2)13(18)9-11-14(19-4)10-7-5-6-8-12(10)17(3)15(11)20-16;/h5-8,13,18H,9H2,1-4H3;1H/q+1;/p-1/t13-;/m0./s1

> <INCHI_KEY>
FQEHWANAXOHLLV-ZOWNYOTGSA-M

> <FORMULA>
C16H20ClNO3

> <MOLECULAR_WEIGHT>
309.79

> <EXACT_MASS>
309.1131712

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.310085319077686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-hydroxy-5-methoxy-2,2,10-trimethyl-2H,3H,4H-pyrano[2,3-b]quinolin-10-ium chloride

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-2.288263355805079

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.637561461380447

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3947306167921925

> <JCHEM_POLAR_SURFACE_AREA>
42.57

> <JCHEM_REFRACTIVITY>
76.893

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-hydroxy-5-methoxy-2,2,10-trimethyl-3H,4H-pyrano[2,3-b]quinolin-10-ium chloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -2.036  -3.716   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.702  -2.946   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.702  -1.406   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.631  -0.636   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.965  -1.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.299  -0.636   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.632  -1.406   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.299   0.904   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.815   0.636   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.825   2.351   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.965   1.674   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.631   0.904   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.702   1.674   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0      -2.036   0.904   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.036  -0.636   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.370  -1.406   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.703  -0.636   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.703   0.904   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.370   1.674   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.702   3.214   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       9.215   0.000   0.000  0.00  0.00          Cl-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀ClNO₃

Average Mass

309.7900 Da

Monoisotopic Mass

309.11317 Da

IUPAC Name

(3S)-3-hydroxy-5-methoxy-2,2,10-trimethyl-2H,3H,4H-pyrano[2,3-b]quinolin-10-ium chloride

Traditional Name

(3S)-3-hydroxy-5-methoxy-2,2,10-trimethyl-3H,4H-pyrano[2,3-b]quinolin-10-ium chloride

CAS Registry Number

Not Available

SMILES

[Cl-].COC1=C2C[C@H](O)C(C)(C)OC2=[N+](C)C2=C1C=CC=C2

InChI Identifier

InChI=1S/C16H20NO3.ClH/c1-16(2)13(18)9-11-14(19-4)10-7-5-6-8-12(10)17(3)15(11)20-16;/h5-8,13,18H,9H2,1-4H3;1H/q+1;/p-1/t13-;/m0./s1

InChI Key

FQEHWANAXOHLLV-ZOWNYOTGSA-M

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
Araliopsis tabouensis	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
Pyranopyridine
Alkyl aryl ether
Benzenoid
Pyridinium
Pyridine
Pyran
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic chloride salt
Organic salt
Organooxygen compound
Organonitrogen compound
Alcohol
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	-1.2	ALOGPS
logP	-2.3	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.89 m³·mol⁻¹	ChemAxon
Polarizability	30.31 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052070

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163184280

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Tabouensinium chloride (NP0083390)

MOL for NP0083390 ((-)-Tabouensinium chloride)

3D MOL for NP0083390 ((-)-Tabouensinium chloride)

3D SDF for NP0083390 ((-)-Tabouensinium chloride)

3D-SDF for NP0083390 ((-)-Tabouensinium chloride)

PDB for NP0083390 ((-)-Tabouensinium chloride)

3D PDB for NP0083390 ((-)-Tabouensinium chloride)

SMILES for NP0083390 ((-)-Tabouensinium chloride)

INCHI for NP0083390 ((-)-Tabouensinium chloride)

Structure for NP0083390 ((-)-Tabouensinium chloride)

3D Structure for NP0083390 ((-)-Tabouensinium chloride)