NP-MRD: Showing NP-Card for Isococculidine (NP0050990)

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Record Information

Version

2.0

Created at

2022-04-27 22:26:57 UTC

Updated at

2022-04-27 22:26:57 UTC

NP-MRD ID

NP0050990

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isococculidine

Description

Isococculidine belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof. Isococculidine is found in Cocculus laurifolius. Isococculidine was first documented in 1988 (PMID: 21401176). Based on a literature review very few articles have been published on Isococculidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
    4.5042    2.9301    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1422    2.6470    0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993    1.3131    0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    0.2982    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1509   -1.0003   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8088   -1.2741   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8540   -0.2670   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569    1.0173   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046   -0.5752   -0.2661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3716    0.5534   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1107    1.4648    0.0026 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1919    2.0049   -0.7140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1080    3.3874   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    0.7932    1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737   -0.3548    1.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049   -1.1293    0.9848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8348   -2.4888    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466   -2.2645   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297   -1.6844   -1.1862 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -2.7033   -1.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557   -2.6624   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6469    4.0265    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9064    2.4754    1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021    2.5215   -0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6844    0.4554    0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814   -1.8064   -0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    1.8331   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    1.1664   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.1870   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354    2.3296    0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544    3.7381    0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261    3.7212   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9030    3.9063   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5494    1.2984    1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7550   -0.8166    2.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4183   -1.2913    1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857   -3.3309    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919   -2.6527    1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -3.2185   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695   -1.5897   -1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -3.7237   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466   -2.7703   -2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -3.1443    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649   -3.3202   -0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
  9 10  1  6
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3  8  1  0
  8  7  2  0
 16 15  1  0
 15 14  2  0
 14 11  1  0
 19  9  1  0
  7  6  1  0
  7  9  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 11 30  1  1
 10 28  1  0
 10 29  1  0
 16 36  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
  5 26  1  0
  4 25  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  8 27  1  0
 15 35  1  0
 14 34  1  0
M  END


  Mrv1652304282200262D          

 21 24  0  0  1  0            999 V2000
    3.7415    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -0.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -0.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    0.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880    1.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    1.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592    1.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344    1.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8384    1.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2672    0.3552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0779    0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -0.5763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8130   -1.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023   -1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294   -0.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0318    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    0.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1615   -0.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4344   -1.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7744   -1.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5992   -0.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
 12 18  1  1  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050990

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@]23[C@H](CCN2CCC2=CC=C(OC)C=C32)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO2/c1-20-15-5-3-13-7-9-19-10-8-14-4-6-16(21-2)12-18(14,19)17(13)11-15/h3-6,11,14,16H,7-10,12H2,1-2H3/t14-,16-,18-/m0/s1

> <INCHI_KEY>
FWXCNFQLKQCXQP-ZVZYQTTQSA-N

> <FORMULA>
C18H23NO2

> <MOLECULAR_WEIGHT>
285.387

> <EXACT_MASS>
285.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.13762418273073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13R,16R)-4,16-dimethoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,14-tetraene

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.3889387863333336

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.219818653065554

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
85.357

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13R,16R)-4,16-dimethoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,14-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.984   0.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.245  -0.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.705  -0.617   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.889   0.916   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.644   2.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.184   2.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.844   3.365   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.304   3.330   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.565   1.979   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.365   0.663   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.879   0.378   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.388  -1.076   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.384  -2.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.871  -1.958   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.362  -0.505   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.059   0.089   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.066   1.624   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.901  -1.361   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.411  -2.815   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.046  -1.897   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.585  -1.862   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9    4   11   15                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    9                                                       
CONECT   18   12   19                                                       
CONECT   19   18                                                            
CONECT   20    2   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₃NO₂

Average Mass

285.3870 Da

Monoisotopic Mass

285.17288 Da

IUPAC Name

(1S,13R,16R)-4,16-dimethoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,14-tetraene

Traditional Name

(1S,13R,16R)-4,16-dimethoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,14-tetraene

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@]23[C@H](CCN2CCC2=CC=C(OC)C=C32)C=C1

InChI Identifier

InChI=1S/C18H23NO2/c1-20-15-5-3-13-7-9-19-10-8-14-4-6-16(21-2)12-18(14,19)17(13)11-15/h3-6,11,14,16H,7-10,12H2,1-2H3/t14-,16-,18-/m0/s1

InChI Key

FWXCNFQLKQCXQP-ZVZYQTTQSA-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
Cocculus laurifolius	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Erythrinanes

Direct Parent

Erythrinanes

Alternative Parents

Substituents

Erythrinane skeleton
Tetrahydroisoquinoline
Indole or derivatives
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:5999 )
Isoquinoline alkaloids (C09546 )

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	2.65	ALOGPS
logP	2.39	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	10.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.36 m³·mol⁻¹	ChemAxon
Polarizability	32.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00001871

Chemspider ID

390765

KEGG Compound ID

C09546

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442300

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Prakash O, Roy R, Jain S, Bhakuni DS: The Complete Assignment of the (1)H- and (13)C-nmr Spectra of Isococculidine. J Nat Prod. 1988 May;51(3):603-5. doi: 10.1021/np50057a032. [PubMed:21401176 ]

Showing NP-Card for Isococculidine (NP0050990)

MOL for NP0050990 (Isococculidine)

3D MOL for NP0050990 (Isococculidine)

3D SDF for NP0050990 (Isococculidine)

3D-SDF for NP0050990 (Isococculidine)

PDB for NP0050990 (Isococculidine)

3D PDB for NP0050990 (Isococculidine)

SMILES for NP0050990 (Isococculidine)

INCHI for NP0050990 (Isococculidine)

Structure for NP0050990 (Isococculidine)

3D Structure for NP0050990 (Isococculidine)