NP-MRD: Showing NP-Card for 3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid (NP0242681)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 03:03:17 UTC

Updated at

2022-09-07 03:03:17 UTC

NP-MRD ID

NP0242681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid

Description

5-Ethenyl-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1,3,5,10,12,14,16-heptaene-4-carboxylic acid belongs to the class of organic compounds known as quinolizines. Quinolizines are compounds containing a quinolizine moiety, which consists of two fused pyridine rings sharing a nitrogen atom. 3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid is found in Vinca major. 5-Ethenyl-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1,3,5,10,12,14,16-heptaene-4-carboxylic acid is a moderately acidic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    5.4134   -0.6384   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7557   -0.3772    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965   -0.1519    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593   -0.6626   -0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985   -0.5224   -0.6360 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5836    0.1403    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832    0.6640    1.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6843    0.5331    1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3869    1.1178    2.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    1.1188    2.8087 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266    1.7769    3.6000 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.8701    0.3168    0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628    0.9126    1.1076 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0070    0.8088    0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614    1.2341    1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4059    0.9899    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3227    0.2852   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0809   -0.1499   -1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431    0.1165   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5894   -0.1900   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425   -0.9005   -1.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003   -1.0981   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9138   -0.6894   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4735   -0.8004   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3337   -0.3602    1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455   -1.2034   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7912    1.2104    2.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170    1.3902    1.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3160    1.7747    1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3959    1.3069    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2022    0.0652   -1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854   -0.6891   -2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714   -0.2975   -2.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318   -1.9105   -2.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -0.6614   -2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7657   -2.1945   -1.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 22  1  0
 22 21  1  0
 21 20  1  0
 20 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  3
  3  8  1  0
 12  6  1  0
 19 14  1  0
 19 20  1  0
  7 27  1  0
 22 35  1  0
 22 36  1  0
 21 33  1  0
 21 34  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
  4 26  1  0
  2 25  1  0
  1 23  1  0
  1 24  1  0
M  CHG  2   5   1  11  -1
M  END


  Mrv1533004171512492D          

 22 25  0  0  0  0            999 V2000
    0.9474   -1.3083    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  CHG  2   1  -1  18   1
M  END
> <DATABASE_ID>
NP0242681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-]C(=O)C1=CC2=[N+](CCC3=C2NC2=CC=CC=C32)C=C1C=C

> <INCHI_IDENTIFIER>
InChI=1S/C18H14N2O2/c1-2-11-10-20-8-7-13-12-5-3-4-6-15(12)19-17(13)16(20)9-14(11)18(21)22/h2-6,9-10H,1,7-8H2,(H,21,22)

> <INCHI_KEY>
ZEVLMKRBFHJUPC-UHFFFAOYSA-N

> <FORMULA>
C18H14N2O2

> <MOLECULAR_WEIGHT>
290.322

> <EXACT_MASS>
290.105527699

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.862733617008956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-ethenyl-6H,7H,12H-5λ⁵-indolo[2,3-a]quinolizin-5-ylium-2-carboxylate

> <ALOGPS_LOGP>
-0.58

> <JCHEM_LOGP>
-1.1676318861384125

> <ALOGPS_LOGS>
-6.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.119106783890906

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.991170713937667

> <JCHEM_POLAR_SURFACE_AREA>
59.8

> <JCHEM_REFRACTIVITY>
97.12339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-ethenyl-6H,7H,12H-5λ⁵-indolo[2,3-a]quinolizin-5-ylium-2-carboxylate

> <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  O   UNK     0       1.768  -2.442   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.998  -0.979   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.071  -4.753   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       9.034  -3.552   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.475  -4.097   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.843  -3.391   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.139  -4.223   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.066  -5.762   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.697  -6.467   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.916  -6.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.223  -7.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.686  -7.504   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.841  -6.217   0.000  0.00  0.00           N+1
HETATM   19  C   UNK     0       4.303  -6.305   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.458  -5.017   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.921  -5.105   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.228  -6.481   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
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    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    4   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
5-Ethenyl-7,17-diazatetracyclo[8.7.0.0,.0,]heptadeca-1,3,5,10,12,14,16-heptaene-4-carboxylate	Generator
5-Ethenyl-7,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,5,10,12,14,16-heptaene-4-carboxylate	Generator

Chemical Formula

C₁₈H₁₄N₂O₂

Average Mass

290.3220 Da

Monoisotopic Mass

290.10553 Da

IUPAC Name

3-ethenyl-6H,7H,12H-5λ⁵-indolo[2,3-a]quinolizin-5-ylium-2-carboxylate

Traditional Name

3-ethenyl-6H,7H,12H-5λ⁵-indolo[2,3-a]quinolizin-5-ylium-2-carboxylate

CAS Registry Number

Not Available

SMILES

[O-]C(=O)C1=CC2=[N+](CCC3=C2NC2=CC=CC=C32)C=C1C=C

InChI Identifier

InChI=1S/C18H14N2O2/c1-2-11-10-20-8-7-13-12-5-3-4-6-15(12)19-17(13)16(20)9-14(11)18(21)22/h2-6,9-10H,1,7-8H2,(H,21,22)

InChI Key

ZEVLMKRBFHJUPC-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
Vinca major	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolizines. Quinolizines are compounds containing a quinolizine moiety, which consists of two fused pyridine rings sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolizines

Sub Class

Not Available

Direct Parent

Quinolizines

Alternative Parents

Substituents

Quinolizine
Indole or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Benzenoid
Heteroaromatic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen 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	-0.58	ALOGPS
logP	-1.2	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.12 m³·mol⁻¹	ChemAxon
Polarizability	31.86 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid (NP0242681)

MOL for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

3D MOL for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

3D SDF for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

3D-SDF for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

PDB for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

3D PDB for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

SMILES for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

INCHI for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

Structure for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)

3D Structure for NP0242681 (3-ethenyl-6h,7h-indolo[2,3-a]quinolizine-2-carboxylic acid)