NP-MRD: Showing NP-Card for 1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol (NP0304841)

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Record Information

Version

2.0

Created at

2022-09-10 20:13:04 UTC

Updated at

2022-09-10 20:13:04 UTC

NP-MRD ID

NP0304841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol

Description

1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol 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. Based on a literature review very few articles have been published on 1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102222132D          

 33 37  0  0  1  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  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 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
    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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    2.0625    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447    2.4750    0.0000 O   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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 32 33  2  0  0  0  0
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 22 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102222132D          

 33 37  0  0  1  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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M  END
> <DATABASE_ID>
NP0304841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC3=CC(OC)=C(OC)C=C3[C@@H]2C[C@@H]1CC1=NCCC2=CC(O)=C(O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H34N2O4/c1-4-16-15-29-8-6-18-12-26(32-2)27(33-3)14-21(18)23(29)10-19(16)9-22-20-13-25(31)24(30)11-17(20)5-7-28-22/h11-14,16,19,23,30-31H,4-10,15H2,1-3H3/t16-,19-,23-/m0/s1

> <INCHI_KEY>
OAIJXTDQJIUEGV-NVVBAYIOSA-N

> <FORMULA>
C27H34N2O4

> <MOLECULAR_WEIGHT>
450.579

> <EXACT_MASS>
450.251857583

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.92089175287973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol

> <JCHEM_LOGP>
3.8122288043599704

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.577074862747804

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.278752421646614

> <JCHEM_PKA_STRONGEST_BASIC>
8.535015619683818

> <JCHEM_POLAR_SURFACE_AREA>
74.52000000000001

> <JCHEM_REFRACTIVITY>
130.57879999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄N₂O₄

Average Mass

450.5790 Da

Monoisotopic Mass

450.25186 Da

IUPAC Name

1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol

Traditional Name

1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CCC3=CC(OC)=C(OC)C=C3[C@@H]2C[C@@H]1CC1=NCCC2=CC(O)=C(O)C=C12

InChI Identifier

InChI=1S/C27H34N2O4/c1-4-16-15-29-8-6-18-12-26(32-2)27(33-3)14-21(18)23(29)10-19(16)9-22-20-13-25(31)24(30)11-17(20)5-7-28-22/h11-14,16,19,23,30-31H,4-10,15H2,1-3H3/t16-,19-,23-/m0/s1

InChI Key

OAIJXTDQJIUEGV-NVVBAYIOSA-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

Not Available

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
Dihydroisoquinoline
Quinolizidine
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Ketimine
Tertiary amine
Tertiary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Imine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen 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	3.81	ChemAxon
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	8.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.58 m³·mol⁻¹	ChemAxon
Polarizability	50.92 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

162943115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol (NP0304841)

MOL for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

3D MOL for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

3D SDF for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

3D-SDF for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

PDB for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

3D PDB for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

SMILES for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

INCHI for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

Structure for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)

3D Structure for NP0304841 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-3,4-dihydroisoquinoline-6,7-diol)