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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:52:04 UTC

Update Date

2022-03-07 02:55:25 UTC

HMDB ID

HMDB0037614

Secondary Accession Numbers

HMDB37614

Metabolite Identification

Common Name

Pteleine

Description

Pteleine belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline. Pteleine has been detected, but not quantified in, herbs and spices. This could make pteleine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pteleine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0037614

> <DATABASE_NAME>
hmdb

> <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

COMPND    HMDB0037614
HETATM    1  C1  UNL     1       4.793   0.049   0.198  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.553   0.437  -0.304  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.343   0.043   0.257  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.247  -0.771   1.365  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.040  -1.151   1.907  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.156  -0.705   1.325  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.340  -1.042   1.807  1.00  0.00           N  
HETATM    8  C6  UNL     1      -2.501  -0.606   1.238  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.764  -0.801   1.529  1.00  0.00           O  
HETATM   10  C7  UNL     1      -4.572  -0.185   0.708  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.786   0.478  -0.209  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.485   0.210   0.129  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.246   0.564  -0.379  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.201   1.387  -1.499  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.195   0.793  -2.784  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.086   0.110   0.215  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.148   0.462  -0.289  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.113   0.691   1.060  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.578   0.070  -0.594  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.737  -1.001   0.540  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.159  -1.124   1.827  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.962  -1.784   2.769  1.00  0.00           H  
HETATM   23  H6  UNL     1      -5.674  -0.180   0.724  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.097   1.097  -1.045  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.706  -0.204  -2.774  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.741   1.469  -3.538  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.275   0.588  -3.026  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.152   1.103  -1.160  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   16
CONECT    7    8    8
CONECT    8    9   12
CONECT    9   10
CONECT   10   11   11   23
CONECT   11   12   24
CONECT   12   13   13
CONECT   13   14   16
CONECT   14   15
CONECT   15   25   26   27
CONECT   16   17   17
CONECT   17   28
END

View in JSmol View Stereo Labels

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 Molecular Weight

229.2313

Monoisotopic Molecular Weight

229.073893223

IUPAC Name

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

Traditional Name

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

CAS Registry Number

2221-41-2

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037614)

Cellular substructure

Membrane (HMDB: HMDB0037614)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037614)

Source

Exogenous

Food

Food (HMDB: HMDB0037614)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037614)

Not Available

Nutrient (HMDB: HMDB0037614)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134 - 135 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.703	31661259
DarkChem	[M-H]-	151.613	31661259
DeepCCS	[M+H]+	150.55	30932474
DeepCCS	[M-H]-	148.192	30932474
DeepCCS	[M-2H]-	181.249	30932474
DeepCCS	[M+Na]+	156.643	30932474
AllCCS	[M+H]+	149.9	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.8	32859911
AllCCS	[M+Na]+	155.0	32859911
AllCCS	[M-H]-	153.9	32859911
AllCCS	[M+Na-2H]-	153.5	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pteleine	COC1=CC2=C(C=C1)N=C1OC=CC1=C2OC	2868.9	Standard polar	33892256
Pteleine	COC1=CC2=C(C=C1)N=C1OC=CC1=C2OC	2093.1	Standard non polar	33892256
Pteleine	COC1=CC2=C(C=C1)N=C1OC=CC1=C2OC	2249.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pteleine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rb-0980000000-187105ad5b49a40f9860	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pteleine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pteleine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pteleine , positive-QTOF	splash10-01q0-0980000000-1f2cffa73a14026e5529	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 10V, Positive-QTOF	splash10-001i-0090000000-e3a9eca4891387c54f7d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 20V, Positive-QTOF	splash10-001i-0090000000-7545a9d198cf4528a135	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 40V, Positive-QTOF	splash10-0uxr-0590000000-1c65ec95373e28d7665e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 10V, Negative-QTOF	splash10-004i-0090000000-259431dbb10036e5f233	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 20V, Negative-QTOF	splash10-004i-0090000000-ca87738429dd5480c07f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 40V, Negative-QTOF	splash10-00xs-0910000000-65ae02ee4b5b80d32fb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 10V, Negative-QTOF	splash10-004i-0090000000-ed4a3dc85d622798a3a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 20V, Negative-QTOF	splash10-004i-0290000000-6b2a9e741706df0a1988	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 40V, Negative-QTOF	splash10-00kb-0910000000-7c7444912942490f7de0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 10V, Positive-QTOF	splash10-001i-0090000000-ade84bbaac177e7ac3e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 20V, Positive-QTOF	splash10-001i-0090000000-ade84bbaac177e7ac3e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pteleine 40V, Positive-QTOF	splash10-001i-0590000000-2d4b2ace38b0a93f3d04	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Pteleine (HMDB0037614)

MOL for HMDB0037614 (Pteleine)

3D MOL for HMDB0037614 (Pteleine)

3D SDF for HMDB0037614 (Pteleine)

3D-SDF for HMDB0037614 (Pteleine)

PDB for HMDB0037614 (Pteleine)

3D PDB for HMDB0037614 (Pteleine)

SMILES for HMDB0037614 (Pteleine)

INCHI for HMDB0037614 (Pteleine)

Structure for HMDB0037614 (Pteleine)

3D Structure for HMDB0037614 (Pteleine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra