NP-MRD: Showing NP-Card for Carcrisine A (NP0069046)

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Record Information

Version

2.0

Created at

2022-04-28 14:18:31 UTC

Updated at

2022-04-28 14:18:31 UTC

NP-MRD ID

NP0069046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carcrisine A

Description

8,9-Dimethoxy-1H,2H,3H-4λ⁵-pyrrolo[2,1-a]isoquinolin-4-ylium belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine. Carcrisine A is found in Carduus crispus. 8,9-Dimethoxy-1H,2H,3H-4λ⁵-pyrrolo[2,1-a]isoquinolin-4-ylium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.0154   -0.9104   -2.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718    0.0543   -1.4179 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -0.0215   -0.9718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -0.9964   -1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192   -0.9950   -0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -1.9407   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489   -1.9096   -0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304   -0.9672    0.0950 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5842   -0.0129    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040   -0.0345    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    0.9139    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8694    0.9413   -0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7583    1.9146    0.3706 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3002    2.8696    1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943    0.8748    1.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601   -0.1047    2.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -0.8073    0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456   -0.7832   -3.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859   -1.9411   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137   -0.7777   -2.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609   -1.7166   -2.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -2.6859   -2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7291   -2.6771   -1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    1.6641    1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3600    3.3650    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    2.3908    2.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724    3.6387    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375    1.6619    0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6481    1.2280    2.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1967    0.4068    2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8136   -0.7986    2.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3217   -0.0806    0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458   -1.7629    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 12  2  0
 12 13  1  0
 13 14  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8 17  1  0
 17 16  1  0
 16 15  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 10  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 14 25  1  0
 14 26  1  0
 14 27  1  0
 11 24  1  0
 17 32  1  0
 17 33  1  0
 16 30  1  0
 16 31  1  0
 15 28  1  0
 15 29  1  0
  7 23  1  0
  6 22  1  0
  4 21  1  0
M  CHG  1   8   1
M  END


  Mrv1533004191513182D          

 17 19  0  0  0  0            999 V2000
   -0.6549   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.1753    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.3140   -0.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597   -2.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  3 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0069046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C3=[N+](CCC3)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16NO2/c1-16-13-8-10-5-7-15-6-3-4-12(15)11(10)9-14(13)17-2/h5,7-9H,3-4,6H2,1-2H3/q+1

> <INCHI_KEY>
BHUXEEVRLQFWKE-UHFFFAOYSA-N

> <FORMULA>
C14H16NO2

> <MOLECULAR_WEIGHT>
230.286

> <EXACT_MASS>
230.117555179

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.792181443995524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8,9-dimethoxy-1H,2H,3H-4λ⁵-pyrrolo[2,1-a]isoquinolin-4-ylium

> <ALOGPS_LOGP>
-1.62

> <JCHEM_LOGP>
-2.621136814471745

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.610503294143196

> <JCHEM_POLAR_SURFACE_AREA>
22.34

> <JCHEM_REFRACTIVITY>
67.16940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,9-dimethoxy-1H,2H,3H-4λ⁵-pyrrolo[2,1-a]isoquinolin-4-ylium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -1.222  -2.753   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.411  -1.444   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.128  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.939  -0.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.479  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.290   1.078   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.829   1.030   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.557  -0.327   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0       8.053  -0.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.166  -2.230   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.740  -2.812   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.746  -1.636   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.207  -1.588   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.395  -2.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.856  -2.849   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.045  -4.158   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.494  -4.110   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆NO₂

Average Mass

230.2860 Da

Monoisotopic Mass

230.11756 Da

IUPAC Name

8,9-dimethoxy-1H,2H,3H-4λ⁵-pyrrolo[2,1-a]isoquinolin-4-ylium

Traditional Name

8,9-dimethoxy-1H,2H,3H-4λ⁵-pyrrolo[2,1-a]isoquinolin-4-ylium

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C3=[N+](CCC3)C=CC2=C1

InChI Identifier

InChI=1S/C14H16NO2/c1-16-13-8-10-5-7-15-6-3-4-12(15)11(10)9-14(13)17-2/h5,7-9H,3-4,6H2,1-2H3/q+1

InChI Key

BHUXEEVRLQFWKE-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, 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
Carduus crispus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Not Available

Direct Parent

Isoquinolines and derivatives

Alternative Parents

Substituents

Isoquinoline
Anisole
Phenol ether
Alkyl aryl ether
Pyridine
Pyridinium
Benzenoid
Heteroaromatic compound
Ether
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic cation
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	-1.6	ALOGPS
logP	-2.6	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	22.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.17 m³·mol⁻¹	ChemAxon
Polarizability	25.79 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

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

10105261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Carcrisine A (NP0069046)

MOL for NP0069046 (Carcrisine A)

3D MOL for NP0069046 (Carcrisine A)

3D SDF for NP0069046 (Carcrisine A)

3D-SDF for NP0069046 (Carcrisine A)

PDB for NP0069046 (Carcrisine A)

3D PDB for NP0069046 (Carcrisine A)

SMILES for NP0069046 (Carcrisine A)

INCHI for NP0069046 (Carcrisine A)

Structure for NP0069046 (Carcrisine A)

3D Structure for NP0069046 (Carcrisine A)