NP-MRD: Showing NP-Card for Ptelein (NP0068524)

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Record Information

Version

2.0

Created at

2022-04-28 13:47:58 UTC

Updated at

2022-04-28 13:47:58 UTC

NP-MRD ID

NP0068524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ptelein

Description

Pteleine, also known as cyclocostunolide, belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline. Pteleine is a strong basic compound (based on its pKa). Outside of the human body, Pteleine has been detected, but not quantified in, herbs and spices. Ptelein is found in Acronychia baeuerlenii, Acronychia bauurlenii, Comptonella sessilifoliola, Drummondita calida, Dutaillyea drupacea, Dutaillyea oreophila, Euodia macrocarpa, Euodia merrilli, Haplophyllum thesioides, Helietta longifoliata, Medicosma cunninghamii, Melicope semecarpifolia, Melicope triphylla, Phellodendron chinense, Philotheca deserti var. deserti, Platydesma campanulata, Ptelea trifoliata , Ruta chalepensis , Ruta graveolens , Teclea nobilis and Zanthoxylum ailanthoides. This could make pteleine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309532D          

 17 19  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15  1  1  0  0  0  0
 15  8  1  0  0  0  0
 16  2  1  0  0  0  0
 16 12  1  0  0  0  0
 17  6  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)N=C1OC=CC1=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO3/c1-15-8-3-4-11-10(7-8)12(16-2)9-5-6-17-13(9)14-11/h3-7H,1-2H3

> <INCHI_KEY>
ALLQMEDAYDKMIO-UHFFFAOYSA-N

> <FORMULA>
C13H11NO3

> <MOLECULAR_WEIGHT>
229.2313

> <EXACT_MASS>
229.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.51267199382209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dimethoxyfuro[2,3-b]quinoline

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.3421433956666666

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.06149060638609

> <JCHEM_POLAR_SURFACE_AREA>
44.49

> <JCHEM_REFRACTIVITY>
61.69940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dimethoxyfuro[2,3-b]quinoline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.465   2.016   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3    4    8                                                       
CONECT    4    3   11                                                       
CONECT    5    6    9                                                       
CONECT    6    5   17                                                       
CONECT    7    8   10                                                       
CONECT    8    3    7   15                                                  
CONECT    9    5   12   13                                                  
CONECT   10    7   11   12                                                  
CONECT   11    4   10   14                                                  
CONECT   12    9   10   16                                                  
CONECT   13    9   14   17                                                  
CONECT   14   11   13                                                       
CONECT   15    1    8                                                       
CONECT   16    2   12                                                       
CONECT   17    6   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
4,6-Dimethoxy-furo(2,3-b)quinoline	HMDB
4,6-Dimethoxyfuro[2,3-b]quinoline, 9ci	HMDB
6-Methoxy dictamine	HMDB
6-Methoxydictamnine	HMDB
Cyclocostunolide	HMDB
Ptelein	HMDB

Chemical Formula

C₁₃H₁₁NO₃

Average Mass

229.2313 Da

Monoisotopic Mass

229.07389 Da

IUPAC Name

4,6-dimethoxyfuro[2,3-b]quinoline

Traditional Name

4,6-dimethoxyfuro[2,3-b]quinoline

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)N=C1OC=CC1=C2OC

InChI Identifier

InChI=1S/C13H11NO3/c1-15-8-3-4-11-10(7-8)12(16-2)9-5-6-17-13(9)14-11/h3-7H,1-2H3

InChI Key

ALLQMEDAYDKMIO-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
Acronychia baeuerlenii	Plant	KNApSAcK
Acronychia bauurlenii	Plant	KNApSAcK
Comptonella sessilifoliola	Plant	KNApSAcK
Drummondita calida	Plant	KNApSAcK
Dutaillyea drupacea	Plant	KNApSAcK
Dutaillyea oreophila	Plant	KNApSAcK
Euodia macrocarpa	Plant	KNApSAcK
Euodia merrilli	Plant	KNApSAcK
Haplophyllum thesioides	Plant	KNApSAcK
Helietta longifoliata	Plant	KNApSAcK
Medicosma cunninghamii	Plant	KNApSAcK
Melicope semecarpifolia	Plant	KNApSAcK
Melicope triphylla	Plant	KNApSAcK
Phellodendron chinense	LOTUS Database	35616633
Philotheca deserti var. deserti	Plant	KNApSAcK
Platydesma campanulata	-	KNApSAcK
Ptelea trifoliata	Plant	KNApSAcK
Ruta chalepensis	Plant	KNApSAcK
Ruta graveolens	Plant	KNApSAcK
Vepris nobilis	Plant	KNApSAcK
Zanthoxylum ailanthoides	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Furanoquinolines

Direct Parent

Furanoquinolines

Alternative Parents

Substituents

Furanoquinoline
Furopyridine
Anisole
Alkyl aryl ether
Pyridine
Benzenoid
Furan
Heteroaromatic compound
Oxacycle
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
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	3.08	ALOGPS
logP	2.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	3.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.7 m³·mol⁻¹	ChemAxon
Polarizability	23.51 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

HMDB0037614

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016727

KNApSAcK ID

C00026477

Chemspider ID

140372

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

159650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ptelein (NP0068524)

MOL for NP0068524 (Ptelein)

3D MOL for NP0068524 (Ptelein)

3D SDF for NP0068524 (Ptelein)

3D-SDF for NP0068524 (Ptelein)

PDB for NP0068524 (Ptelein)

3D PDB for NP0068524 (Ptelein)

SMILES for NP0068524 (Ptelein)

INCHI for NP0068524 (Ptelein)

Structure for NP0068524 (Ptelein)

3D Structure for NP0068524 (Ptelein)