NP-MRD: Showing NP-Card for Haplopine (NP0051230)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:37:24 UTC

Updated at

2022-04-27 22:37:24 UTC

NP-MRD ID

NP0051230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haplopine

Description

4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol, also known as heliparvifoline, belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline. Haplopine is found in Aegle marmelos , Afraegle paniculata , Dictamnus albus , Dictamnus dasycarpus , Dutaillyea baudouinii, Euodia fargesii, Geijera balansae, Haplophyllum acutifolium , Haplophyllum bucharicum Litv., Haplophyllum cappadocicum, Haplophyllum dauricum, Haplophyllum dubium, Haplophyllum ferganicum, Haplophyllum foliosum, Haplophyllum latifolium, Haplophyllum obtusifolium, Haplophyllum patavinum, Haplophyllum pedicellatum, Haplophyllum perforatum, Haplophyllum ramosissimum, Haplophyllum robustum, Haplophyllum thesioides, Haplophyllum vucanicum, Melicope lasioneura, Melicope semecarpifolia, Monnieria trifolia, Oricia suaveolens, Sarcomelicope glauca, Skimmia laureola, Skimmia reevesiana, Toddalia asiatica , Vepris suaveolens, Zanthoxylum ailanthoides, Zanthoxylum arnottianum, Zanthoxylum beecheyanum, Zanthoxylum bungeanum , Zanthoxylum cuspidatum, Zanthoxylum dissitum, Zanthoxylum integrifoliolum, Zanthoxylum microcarpum, Zanthoxylum nitidum , Zanthoxylum rhoifolium and Zanthoxylum simulans. 4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.5363   -1.3609    0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634   -0.8549   -0.8646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102   -0.0625   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.3095   -0.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6538    2.1807   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    3.4431   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178    3.3214   -0.1743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    2.0744   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479    1.5015    0.2607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7714    0.1662    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667   -0.4123    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0182    0.3657    0.9813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133    0.8924    0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0864   -1.7786    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -2.3442    0.9647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0109   -2.5959    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -2.0065   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3170   -0.6404   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -2.0516   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532   -0.5374    0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613   -1.9430    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477    1.9001   -1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7158    4.3503   -0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1110    1.9948    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0034    0.3833    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7221    0.7161   -0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -1.7417    1.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -3.6662    0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -2.6037   -0.4443 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  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  3  1  0
  8  4  1  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
 13 24  1  0
 13 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv1533004181503072D          

 18 20  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.0000    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
    2.8579    0.8250    0.0000 O   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  3 18  2  0  0  0  0
  8 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=NC2=C(OC)C(O)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO4/c1-16-11-7-3-4-9(15)12(17-2)10(7)14-13-8(11)5-6-18-13/h3-6,15H,1-2H3

> <INCHI_KEY>
LJKPBWHZRNQEMO-UHFFFAOYSA-N

> <FORMULA>
C13H11NO4

> <MOLECULAR_WEIGHT>
245.234

> <EXACT_MASS>
245.068807838

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
24.416302791079225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dimethoxyfuro[2,3-b]quinolin-7-ol

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.0385780739999997

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.841514041959111

> <JCHEM_PKA_STRONGEST_BASIC>
1.8233926524476796

> <JCHEM_POLAR_SURFACE_AREA>
64.72

> <JCHEM_REFRACTIVITY>
63.6803

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
haplopine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    3    8                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
Heliparvifoline	Kegg

Chemical Formula

C₁₃H₁₁NO₄

Average Mass

245.2340 Da

Monoisotopic Mass

245.06881 Da

IUPAC Name

4,8-dimethoxyfuro[2,3-b]quinolin-7-ol

Traditional Name

haplopine

CAS Registry Number

Not Available

SMILES

COC1=C2C=COC2=NC2=C(OC)C(O)=CC=C12

InChI Identifier

InChI=1S/C13H11NO4/c1-16-11-7-3-4-9(15)12(17-2)10(7)14-13-8(11)5-6-18-13/h3-6,15H,1-2H3

InChI Key

LJKPBWHZRNQEMO-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
Aegle marmelos	Plant	KNApSAcK
Afraegle paniculata	Plant	KNApSAcK
Dictamnus albus	Plant	KNApSAcK
Dictamnus dasycarpus	Plant	KNApSAcK
Dutaillyea baudouinii	Plant	KNApSAcK
Euodia fargesii	Plant	KNApSAcK
Geijera balansae	Plant	KNApSAcK
Haplophyllum acutifolium	Plant	KNApSAcK
Haplophyllum bucharicum	Plant	KNApSAcK
Haplophyllum cappadocicum	Plant	KNApSAcK
Haplophyllum dauricum	Plant	KNApSAcK
Haplophyllum dubium	Plant	KNApSAcK
Haplophyllum ferganicum	Plant	KNApSAcK
Haplophyllum foliosum	Plant	KNApSAcK
Haplophyllum latifolium	Plant	KNApSAcK
Haplophyllum obtusifolium	Plant	KNApSAcK
Haplophyllum patavinum	Plant	KNApSAcK
Haplophyllum pedicellatum	Plant	KNApSAcK
Haplophyllum perforatum	Plant	KNApSAcK
Haplophyllum ramosissimum	Plant	KNApSAcK
Haplophyllum robustum	Plant	KNApSAcK
Haplophyllum thesioides	LOTUS Database	35616633
Haplophyllum vucanicum	Plant	KNApSAcK
Melicope lasioneura	Plant	KNApSAcK
Melicope semecarpifolia	Plant	KNApSAcK
Monnieria trifolia	Plant	KNApSAcK
Oricia suaveolens	Plant	KNApSAcK
Sarcomelicope glauca	Plant	KNApSAcK
Skimmia laureola	Plant	KNApSAcK
Skimmia reevesiana	Plant	KNApSAcK
Toddalia asiatica	Plant	KNApSAcK
Vepris suaveolens	LOTUS Database	35616633
Zanthoxylum ailanthoides	Plant	KNApSAcK
Zanthoxylum arnottianum	Plant	KNApSAcK
Zanthoxylum beecheyanum	LOTUS Database	35616633
Zanthoxylum bungeanum	Plant	KNApSAcK
Zanthoxylum cuspidatum	Plant	KNApSAcK
Zanthoxylum dissitum	Plant	KNApSAcK
Zanthoxylum integrifoliolum	Plant	KNApSAcK
Zanthoxylum microcarpum	Plant	KNApSAcK
Zanthoxylum nitidum	Plant	KNApSAcK
Zanthoxylum rhoifolium	Plant	KNApSAcK
Zanthoxylum simulans	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
1-hydroxy-2-unsubstituted benzenoid
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

organic heterotricyclic compound (CHEBI:5620 )
oxacycle (CHEBI:5620 )
organonitrogen heterocyclic compound (CHEBI:5620 )
Quinoline alkaloids (C10694 )

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	2.51	ALOGPS
logP	2.04	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	1.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.68 m³·mol⁻¹	ChemAxon
Polarizability	24.42 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002172

Chemspider ID

Not Available

KEGG Compound ID

C10694

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281846

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Haplopine (NP0051230)

MOL for NP0051230 (Haplopine)

3D MOL for NP0051230 (Haplopine)

3D SDF for NP0051230 (Haplopine)

3D-SDF for NP0051230 (Haplopine)

PDB for NP0051230 (Haplopine)

3D PDB for NP0051230 (Haplopine)

SMILES for NP0051230 (Haplopine)

INCHI for NP0051230 (Haplopine)

Structure for NP0051230 (Haplopine)

3D Structure for NP0051230 (Haplopine)