NP-MRD: Showing NP-Card for Nostocarboline (NP0006163)

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Record Information

Version

2.0

Created at

2020-12-09 03:12:44 UTC

Updated at

2021-07-15 16:54:01 UTC

NP-MRD ID

NP0006163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nostocarboline

Provided By

NPAtlas

Description

Nostocarboline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Nostocarboline is found in Nostoc. Nostocarboline was first documented in 2005 (PMID: 16378379). Based on a literature review a small amount of articles have been published on Nostocarboline (PMID: 16468755) (PMID: 20714150) (PMID: 21797171) (PMID: 22289366).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118253D          

 25 27  0  0  0  0            999 V2000
    4.2095   -0.3857    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -0.0854   -0.0615 N   0  3  0  0  0  4  0  0  0  0  0  0
    2.3545    1.0620   -0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016    1.2903   -0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631    0.4080   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -0.7623    0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868   -0.9616    0.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693   -1.4295    0.7572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7054   -0.7735    0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579   -1.0472    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0429   -0.1767    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494    0.9911   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8864    2.1124   -0.9047 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    1.2736   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.3957   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009    0.1957   -0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2908   -1.4824   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5626   -0.1680    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0993    1.7489   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    2.1968   -1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -1.8725    0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218   -2.3622    1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129   -1.9700    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1052   -0.3834    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763    2.1859   -1.0523 H   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7  2  1  0  0  0  0
 15  9  1  0  0  0  0
 15  5  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4 20  1  0  0  0  0
  7 21  1  0  0  0  0
  8 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 14 25  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
NP0006163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C([H])=C(Cl)C([H])=C2C2=C([H])C([H])=[N+](C([H])=C12)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H9ClN2/c1-15-5-4-9-10-6-8(13)2-3-11(10)14-12(9)7-15/h2-7H,1H3/p+1

> <INCHI_KEY>
RGQUDRQSJYJYAQ-UHFFFAOYSA-O

> <FORMULA>
C12H10ClN2

> <MOLECULAR_WEIGHT>
217.68

> <EXACT_MASS>
217.0527025

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
23.483930500625366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-chloro-2-methyl-9H-pyrido[3,4-b]indol-2-ium

> <ALOGPS_LOGP>
-2.16

> <JCHEM_LOGP>
-1.4661104211384117

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.374520164932232

> <JCHEM_POLAR_SURFACE_AREA>
19.669999999999998

> <JCHEM_REFRACTIVITY>
62.2755

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-chloro-2-methyl-9H-pyrido[3,4-b]indol-2-ium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.210  -0.386   0.039  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.780  -0.085  -0.062  0.00  0.00           N+1
HETATM    3  C   UNK     0       2.354   1.062  -0.637  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.002   1.290  -0.703  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.063   0.408  -0.213  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.518  -0.762   0.373  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.887  -0.962   0.424  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.569  -1.430   0.757  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.705  -0.774   0.462  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.058  -1.047   0.654  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.043  -0.177   0.243  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.649   0.991  -0.374  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -4.886   2.112  -0.905  0.00  0.00          Cl+0
HETATM   14  C   UNK     0      -2.293   1.274  -0.570  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.314   0.396  -0.155  0.00  0.00           C+0
HETATM   16  H   UNK     0       4.801   0.196  -0.685  0.00  0.00           H+0
HETATM   17  H   UNK     0       4.291  -1.482  -0.145  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.563  -0.168   1.079  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.099   1.749  -1.018  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.627   2.197  -1.156  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.240  -1.873   0.880  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.522  -2.362   1.236  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.313  -1.970   1.139  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.105  -0.383   0.389  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.976   2.186  -1.052  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2   21                                                  
CONECT    8    6    9   22                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   25                                                  
CONECT   15   14    9    5                                                  
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    4                                                            
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₂H₁₀ClN₂

Average Mass

217.6800 Da

Monoisotopic Mass

217.05270 Da

IUPAC Name

6-chloro-2-methyl-9H-pyrido[3,4-b]indol-2-ium

Traditional Name

6-chloro-2-methyl-9H-pyrido[3,4-b]indol-2-ium

CAS Registry Number

Not Available

SMILES

C[N+]1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1

InChI Identifier

InChI=1S/C12H9ClN2/c1-15-5-4-9-10-6-8(13)2-3-11(10)14-12(9)7-15/h2-7H,1H3/p+1

InChI Key

RGQUDRQSJYJYAQ-UHFFFAOYSA-O

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
Nostoc	NPAtlas	16378379

Species Where Detected

Species Name	Source	Reference
Nostoc 78-12A	KNApSAcK Database	22123792
Nostoc sp.	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as beta carbolines. These are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Indole
Aryl chloride
Aryl halide
Pyridine
Pyridinium
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:66637 )
alkaloid (CHEBI:66637 )
organic cation (CHEBI:66637 )
beta-carbolines (CHEBI:66637 )

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	-2.2	ALOGPS
logP	-1.5	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	11.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.28 m³·mol⁻¹	ChemAxon
Polarizability	23.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005779

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034081

Chemspider ID

4483628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nostocarboline

METLIN ID

Not Available

PubChem Compound

5326150

PDB ID

Not Available

ChEBI ID

66637

Good Scents ID

Not Available

References

General References

Becher PG, Beuchat J, Gademann K, Juttner F: Nostocarboline: isolation and synthesis of a new cholinesterase inhibitor from Nostoc 78-12A. J Nat Prod. 2005 Dec;68(12):1793-5. doi: 10.1021/np050312l. [PubMed:16378379 ]
Blom JF, Brutsch T, Barbaras D, Bethuel Y, Locher HH, Hubschwerlen C, Gademann K: Potent algicides based on the cyanobacterial alkaloid nostocarboline. Org Lett. 2006 Feb 16;8(4):737-40. doi: 10.1021/ol052968b. [PubMed:16468755 ]
Locher HH, Ritz D, Pfaff P, Gaertner M, Knezevic A, Sabato D, Schroeder S, Barbaras D, Gademann K: Dimers of nostocarboline with potent antibacterial activity. Chemotherapy. 2010;56(4):318-24. doi: 10.1159/000320033. Epub 2010 Aug 13. [PubMed:20714150 ]
Gademann K: Out in the green: biologically active metabolites produced by cyanobacteria. Chimia (Aarau). 2011;65(6):416-9. doi: 10.2533/chimia.2011.416. [PubMed:21797171 ]
Gademann K, Sieber S: Chemical interference of biological systems with natural products. Chimia (Aarau). 2011;65(11):835-8. doi: 10.2533/chimia.2011.835. [PubMed:22289366 ]

Showing NP-Card for Nostocarboline (NP0006163)

MOL for NP0006163 (Nostocarboline)

3D MOL for NP0006163 (Nostocarboline)

3D SDF for NP0006163 (Nostocarboline)

3D-SDF for NP0006163 (Nostocarboline)

PDB for NP0006163 (Nostocarboline)

3D PDB for NP0006163 (Nostocarboline)

SMILES for NP0006163 (Nostocarboline)

INCHI for NP0006163 (Nostocarboline)

Structure for NP0006163 (Nostocarboline)

3D Structure for NP0006163 (Nostocarboline)