NP-MRD: Showing NP-Card for (2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine (NP0222660)

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Record Information

Version

2.0

Created at

2022-09-06 00:33:06 UTC

Updated at

2022-09-06 00:33:06 UTC

NP-MRD ID

NP0222660

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine

Description

CHEMBL459625 belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. (2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine is found in Strychnos potatorum. Based on a literature review very few articles have been published on CHEMBL459625.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202332D          

 33 39  0  0  1  0            999 V2000
   11.7202   -3.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4850   -6.3218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2920   -6.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5469   -7.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309062202332D          

 33 39  0  0  1  0            999 V2000
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 25 33  1  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC3C(NC4=CC=CC=C34)[C@@H]2C[C@@H]1C[C@H]1NCCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C29H36N4/c1-2-18-17-33-14-12-23-21-8-4-6-10-25(21)32-29(23)27(33)16-19(18)15-26-28-22(11-13-30-26)20-7-3-5-9-24(20)31-28/h3-10,18-19,23,26-27,29-32H,2,11-17H2,1H3/t18-,19-,23?,26+,27-,29?/m0/s1

> <INCHI_KEY>
WPRCHZNIQPXBQO-IWOKYBKVSA-N

> <FORMULA>
C29H36N4

> <MOLECULAR_WEIGHT>
440.635

> <EXACT_MASS>
440.293997175

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.21933959566068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,12bS)-3-ethyl-2-{[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-1H,2H,3H,4H,6H,7H,7aH,12H,12aH,12bH-indolo[2,3-a]quinolizine

> <JCHEM_LOGP>
4.638938230333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.38268192952092

> <JCHEM_PKA_STRONGEST_BASIC>
10.104035763178738

> <JCHEM_POLAR_SURFACE_AREA>
43.089999999999996

> <JCHEM_REFRACTIVITY>
136.94230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,12bS)-3-ethyl-2-[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl]-1H,2H,3H,4H,6H,7H,7aH,12H,12aH,12bH-indolo[2,3-a]quinolizine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      21.878  -7.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.847  -8.551   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.323 -10.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.829 -10.336   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      23.305 -11.801   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      24.812 -12.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.288 -13.585   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.257 -14.730   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.418 -16.261   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.664 -17.167   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.503 -18.698   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.096 -19.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.850 -18.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.011 -16.888   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      21.981 -15.743   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      22.751 -14.410   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.275 -12.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.769 -12.625   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.293 -11.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.786 -10.840   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.310  -9.375   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      19.341  -8.231   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      18.865  -6.766   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.359  -6.446   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.328  -7.591   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.804  -9.055   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      15.558  -9.960   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      14.312  -9.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.806  -9.375   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.775  -8.231   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.251  -6.766   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.758  -6.446   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.788  -7.591   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   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   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   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   25   28                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆N₄

Average Mass

440.6350 Da

Monoisotopic Mass

440.29400 Da

IUPAC Name

(2S,3R,12bS)-3-ethyl-2-{[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]methyl}-1H,2H,3H,4H,6H,7H,7aH,12H,12aH,12bH-indolo[2,3-a]quinolizine

Traditional Name

(2S,3R,12bS)-3-ethyl-2-[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-ylmethyl]-1H,2H,3H,4H,6H,7H,7aH,12H,12aH,12bH-indolo[2,3-a]quinolizine

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CCC3C(NC4=CC=CC=C34)[C@@H]2C[C@@H]1C[C@H]1NCCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C29H36N4/c1-2-18-17-33-14-12-23-21-8-4-6-10-25(21)32-29(23)27(33)16-19(18)15-26-28-22(11-13-30-26)20-7-3-5-9-24(20)31-28/h3-10,18-19,23,26-27,29-32H,2,11-17H2,1H3/t18-,19-,23?,26+,27-,29?/m0/s1

InChI Key

WPRCHZNIQPXBQO-IWOKYBKVSA-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
Strychnos potatorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Quinolizidine
Quinolizine
3-alkylindole
Indole
Indole or derivatives
Dihydroindole
Secondary aliphatic/aromatic amine
Aralkylamine
Piperidine
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Secondary amine
Azacycle
Organoheterocyclic compound
Secondary aliphatic amine
Organonitrogen compound
Hydrocarbon derivative
Amine
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	4.64	ChemAxon
pKa (Strongest Acidic)	16.38	ChemAxon
pKa (Strongest Basic)	10.1	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.94 m³·mol⁻¹	ChemAxon
Polarizability	52.22 Å³	ChemAxon
Number of Rings	7	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

23327554

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559929

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine (NP0222660)

MOL for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

3D MOL for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

3D SDF for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

3D-SDF for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

PDB for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

3D PDB for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

SMILES for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

INCHI for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

Structure for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)

3D Structure for NP0222660 ((2s,3r,12bs)-3-ethyl-2-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-ylmethyl]-1h,2h,3h,4h,6h,7h,7ah,12h,12ah,12bh-indolo[2,3-a]quinolizine)