NP-MRD: Showing NP-Card for Grandirubrine (NP0068026)

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Record Information

Version

2.0

Created at

2022-04-28 12:54:41 UTC

Updated at

2022-04-28 12:54:41 UTC

NP-MRD ID

NP0068026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Grandirubrine

Description

Grandirubrine 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. Grandirubrine is found in Abuta concolor, Abuta grandifolia, Abuta grandifolia (Mart.) Sandw.Kew. and Cissampelos pareira L. . Grandirubrine is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.1057    2.5418   -1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8029    2.1384    0.1743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    1.0691    0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5729    1.2647    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050    2.5473    0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    3.1792   -0.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043    0.2074    0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2634   -1.0453    0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -1.9995    0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783   -3.2699    0.8581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0459   -3.5754    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0418   -2.6346    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097   -1.3136    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509   -0.2316    0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7983   -0.4700    0.2981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353   -0.6962   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782   -1.2845    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -1.9055    0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -1.3247    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4788   -2.1369    1.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8030   -0.0234    0.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966    0.1335    0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0027    1.1243    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    1.1373    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7583    0.0792    0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718    2.1690   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    3.6391   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3410    2.1302   -1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179    3.6424   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985    3.9674   -1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1969    2.4439   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758   -4.6201    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -2.8440    0.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -0.4622   -1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011   -1.7279   -1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2763    0.0139   -1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -2.9593    1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -3.0752    1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5266    2.0624    0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060    2.1093    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 14  1  0
 14 15  1  0
 15 16  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9 17  1  0
 17 25  2  0
 25 24  1  0
 24 23  2  0
 23 21  1  0
 21 22  2  0
 21 19  1  0
 19 20  1  0
 19 18  2  0
 25  7  1  0
  7  8  2  0
  7  4  1  0
  8 13  1  0
  8  9  1  0
 18 17  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 12 33  1  0
 11 32  1  0
 24 40  1  0
 23 39  1  0
 20 38  1  0
 18 37  1  0
M  END


  Mrv1533004231519462D          

 25 28  0  0  0  0            999 V2000
   -0.2877    0.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5221    0.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    0.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    1.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9515    1.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -0.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2398   -0.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813   -0.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486   -1.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9640   -0.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6446   -1.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0886   -0.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8775    0.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5287    0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7059    0.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057   -1.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055   -2.2787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9462   -2.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2871   -2.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -1.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7953   -0.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145   -0.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -1.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -0.9636    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
  7 25  2  0  0  0  0
 17 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2C=CN=C3C4=C(C=CC(=O)C(O)=C4)C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C19H15NO5/c1-23-17-10-6-7-20-16-11-8-13(22)12(21)5-4-9(11)15(14(10)16)18(24-2)19(17)25-3/h4-8H,1-3H3,(H,21,22)

> <INCHI_KEY>
SKNSHDGCCINVFT-UHFFFAOYSA-N

> <FORMULA>
C19H15NO5

> <MOLECULAR_WEIGHT>
337.331

> <EXACT_MASS>
337.095022587

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.85396311467476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-14,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁸.0¹³,¹⁷]heptadeca-1(17),2(8),3,6,9,11,13,15-octaen-5-one

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
1.8306894353333327

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.014865356835164

> <JCHEM_PKA_STRONGEST_BASIC>
4.48204057477962

> <JCHEM_POLAR_SURFACE_AREA>
77.88000000000001

> <JCHEM_REFRACTIVITY>
94.12589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-14,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁸.0¹³,¹⁷]heptadeca-1(17),2(8),3,6,9,11,13,15-octaen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -0.537   1.392   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.975   1.687   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.985   0.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.497   0.819   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.998   2.276   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.509   2.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.508  -0.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.048  -0.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.498  -1.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.931  -2.407   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.266  -1.640   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.537  -2.510   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.499  -0.117   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.971   0.334   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.454   1.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.918   0.902   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.237  -2.725   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.050  -4.254   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.633  -4.856   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.403  -3.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.495  -2.093   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.485  -0.931   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.027  -1.226   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.528  -2.682   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.007  -1.799   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8   25                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    8                                                       
CONECT   17    9   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21    3   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   21    7   17                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₅NO₅

Average Mass

337.3310 Da

Monoisotopic Mass

337.09502 Da

IUPAC Name

6-hydroxy-14,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁸.0¹³,¹⁷]heptadeca-1(17),2(8),3,6,9,11,13,15-octaen-5-one

Traditional Name

6-hydroxy-14,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁸.0¹³,¹⁷]heptadeca-1(17),2(8),3,6,9,11,13,15-octaen-5-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(OC)=C2C=CN=C3C4=C(C=CC(=O)C(O)=C4)C1=C23

InChI Identifier

InChI=1S/C19H15NO5/c1-23-17-10-6-7-20-16-11-8-13(22)12(21)5-4-9(11)15(14(10)16)18(24-2)19(17)25-3/h4-8H,1-3H3,(H,21,22)

InChI Key

SKNSHDGCCINVFT-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
Abuta concolor	Plant	KNApSAcK
Abuta grandifolia	LOTUS Database	35616633
Abuta grandifolia (Mart.) Sandw.Kew.	Plant	KNApSAcK
Cissampelos pareira	Plant	KNApSAcK

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
Tropolone
Anisole
Phenol ether
Tropone
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Cyclic ketone
Azacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
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	1.57	ALOGPS
logP	1.83	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	4.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.13 m³·mol⁻¹	ChemAxon
Polarizability	34.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

630768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Grandirubrine (NP0068026)

MOL for NP0068026 (Grandirubrine)

3D MOL for NP0068026 (Grandirubrine)

3D SDF for NP0068026 (Grandirubrine)

3D-SDF for NP0068026 (Grandirubrine)

PDB for NP0068026 (Grandirubrine)

3D PDB for NP0068026 (Grandirubrine)

SMILES for NP0068026 (Grandirubrine)

INCHI for NP0068026 (Grandirubrine)

Structure for NP0068026 (Grandirubrine)

3D Structure for NP0068026 (Grandirubrine)