NP-MRD: Showing NP-Card for 1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol (NP0217487)

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Record Information

Version

2.0

Created at

2022-09-05 17:51:16 UTC

Updated at

2022-09-05 17:51:16 UTC

NP-MRD ID

NP0217487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

Description

1-({3-Ethyl-10-hydroxy-9-methoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei. 1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol is found in Alangium longiflorum and Carapichea ipecacuanha. 1-({3-Ethyl-10-hydroxy-9-methoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171518362D          

 33 37  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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 N   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
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    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004171518362D          

 33 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0217487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CN2CCC3=CC(OC)=C(O)C=C3C2CC1CC1NCCC2=CC(O)=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H36N2O4/c1-4-16-15-29-8-6-18-12-26(32-2)25(31)13-21(18)23(29)10-19(16)9-22-20-14-27(33-3)24(30)11-17(20)5-7-28-22/h11-14,16,19,22-23,28,30-31H,4-10,15H2,1-3H3

> <INCHI_KEY>
QBNRQKFLWJOWBD-UHFFFAOYSA-N

> <FORMULA>
C27H36N2O4

> <MOLECULAR_WEIGHT>
452.595

> <EXACT_MASS>
452.267507647

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.07728063386594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-({3-ethyl-10-hydroxy-9-methoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
3.690336023342332

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
10.401340278632118

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.834226414869757

> <JCHEM_PKA_STRONGEST_BASIC>
9.030814335845314

> <JCHEM_POLAR_SURFACE_AREA>
74.19000000000001

> <JCHEM_REFRACTIVITY>
130.78609999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-({3-ethyl-10-hydroxy-9-methoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   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      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.668   2.310   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    3   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   21   25                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆N₂O₄

Average Mass

452.5950 Da

Monoisotopic Mass

452.26751 Da

IUPAC Name

1-({3-ethyl-10-hydroxy-9-methoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

Traditional Name

1-({3-ethyl-10-hydroxy-9-methoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

CAS Registry Number

Not Available

SMILES

CCC1CN2CCC3=CC(OC)=C(O)C=C3C2CC1CC1NCCC2=CC(O)=C(OC)C=C12

InChI Identifier

InChI=1S/C27H36N2O4/c1-4-16-15-29-8-6-18-12-26(32-2)25(31)13-21(18)23(29)10-19(16)9-22-20-14-27(33-3)24(30)11-17(20)5-7-28-22/h11-14,16,19,22-23,28,30-31H,4-10,15H2,1-3H3

InChI Key

QBNRQKFLWJOWBD-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Alangium longiflorum	LOTUS Database	35616633
Cephaelis ipecacuanha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Emetine alkaloids

Sub Class

Not Available

Direct Parent

Emetine alkaloids

Alternative Parents

Substituents

Emetine alkaloid
Tetrahydroisoquinoline
Quinolizidine
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Piperidine
Tertiary aliphatic amine
Tertiary amine
Secondary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen 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	3.73	ALOGPS
logP	3.69	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	9.03	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.19 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.79 m³·mol⁻¹	ChemAxon
Polarizability	52.08 Å³	ChemAxon
Number of Rings	5	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

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

53463261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol (NP0217487)

MOL for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

3D MOL for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

3D SDF for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

3D-SDF for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

PDB for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

3D PDB for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

SMILES for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

INCHI for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

Structure for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)

3D Structure for NP0217487 (1-({3-ethyl-10-hydroxy-9-methoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl}methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol)