NP-MRD: Showing NP-Card for Galipine (NP0051222)

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Record Information

Version

2.0

Created at

2022-04-27 22:37:08 UTC

Updated at

2022-04-27 22:37:08 UTC

NP-MRD ID

NP0051222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Galipine

Description

Galipine belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. Galipine is found in Angostura trifoliata, Cusparia febrifuga and Galipea officinalis . Galipine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    6.6584    1.8399   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0003    0.6174   -0.5760 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6518    0.4547   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815    1.5268    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6508    1.4431    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9999    0.2616    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730    0.1425    0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248    0.5976   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669    0.5101   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3194   -0.6775   -0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6642   -0.8398   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2883   -2.0334   -0.5167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5260   -3.0860   -1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3327    0.2429    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6729    0.1060    0.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3849    1.1659    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7122    2.3314    1.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3613    2.4795    1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785    1.4199    0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    1.5315    0.3921 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384   -0.7991   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846   -0.7274   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -1.7849   -1.0828 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0881   -3.0215   -1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7502    1.7582   -0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4869    2.1088    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2201    2.6803   -0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4923    2.4576    0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211    2.2644    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -0.8777    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416    0.8682    1.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679    0.0410   -1.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0251    1.6666   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7881   -1.5194   -0.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6685   -3.3432   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504   -3.9728   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0371   -2.7763   -2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1764   -0.8033    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4305    1.1118    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2725    3.1702    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8667    3.4293    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344   -1.7409   -0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -2.9660   -1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844   -3.6814   -0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6766   -3.5770   -2.1700 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 20  9  1  0
 19 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
 24 43  1  0
 24 44  1  0
 24 45  1  0
M  END


  Mrv1533005011511262D          

 24 26  0  0  0  0            999 V2000
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    0.7145   -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
    1.4289    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
    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
    3.5724   -0.4125    0.0000 C   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 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
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CCC2=CC(OC)=C3C=CC=CC3=N2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO3/c1-22-18-11-9-14(12-20(18)24-3)8-10-15-13-19(23-2)16-6-4-5-7-17(16)21-15/h4-7,9,11-13H,8,10H2,1-3H3

> <INCHI_KEY>
XYXVQWAPEQXRET-UHFFFAOYSA-N

> <FORMULA>
C20H21NO3

> <MOLECULAR_WEIGHT>
323.392

> <EXACT_MASS>
323.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.46995978059461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxyquinoline

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
4.068165328

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.364591226734799

> <JCHEM_POLAR_SURFACE_AREA>
40.58

> <JCHEM_REFRACTIVITY>
93.28330000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galipine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19    9                                                       
CONECT   21    6   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₁NO₃

Average Mass

323.3920 Da

Monoisotopic Mass

323.15214 Da

IUPAC Name

2-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxyquinoline

Traditional Name

galipine

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CCC2=CC(OC)=C3C=CC=CC3=N2)C=C1OC

InChI Identifier

InChI=1S/C20H21NO3/c1-22-18-11-9-14(12-20(18)24-3)8-10-15-13-19(23-2)16-6-4-5-7-17(16)21-15/h4-7,9,11-13H,8,10H2,1-3H3

InChI Key

XYXVQWAPEQXRET-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
Angostura trifoliata	-	KNApSAcK
Cusparia febrifuga	Plant	KNApSAcK
Galipea officinalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Not Available

Direct Parent

Quinolines and derivatives

Alternative Parents

Substituents

Quinoline
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
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	4.26	ALOGPS
logP	4.07	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	6.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	93.28 m³·mol⁻¹	ChemAxon
Polarizability	36.47 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

68235

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Galipine (NP0051222)

MOL for NP0051222 (Galipine)

3D MOL for NP0051222 (Galipine)

3D SDF for NP0051222 (Galipine)

3D-SDF for NP0051222 (Galipine)

PDB for NP0051222 (Galipine)

3D PDB for NP0051222 (Galipine)

SMILES for NP0051222 (Galipine)

INCHI for NP0051222 (Galipine)

Structure for NP0051222 (Galipine)

3D Structure for NP0051222 (Galipine)