NP-MRD: Showing NP-Card for (+)-Coculine (NP0067959)

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Record Information

Version

2.0

Created at

2022-04-28 12:48:08 UTC

Updated at

2022-04-28 12:48:08 UTC

NP-MRD ID

NP0067959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Coculine

Description

COCCULINE, also known as cucoline or sinomenine, 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. (+)-Coculine is found in Cocculus carolinus DC., Cocculus laurifolius, Cocculus laurifolius DC., Cocculus orbiculatus and Cocculus trilobus DC. . (+)-Coculine was first documented in 2012 (PMID: 23244208). Based on a literature review very few articles have been published on COCCULINE (PMID: 34061521).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    4.3898    0.5613    1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3256   -0.0819    0.4084 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3130    0.8254    0.0974 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1445    0.9761   -1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028   -0.1690   -1.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -0.8069   -1.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4279   -1.9786   -1.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070   -2.7343   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -1.7182    0.7504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1143   -1.8113    1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.5277    2.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0688    0.2824    1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2423    0.9597    0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    1.6744   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282    1.7303   -1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227    2.4591   -2.4403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4404    1.0183   -1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1711    0.3050   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1139   -0.4436    0.1046 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0736    0.4357    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -0.1354    1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    1.0991    1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7237    1.3683    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425    1.8184    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655    0.9625   -1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6976    1.9454   -1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306   -0.4711   -2.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -2.5557   -2.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820   -1.6632   -1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -3.2403   -0.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -3.4500   -0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -2.3752    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373   -2.4485    2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9679    0.0695    2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6190   -0.7571    2.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9299    0.9130    1.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441    2.2093   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142    3.4379   -2.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537    1.0608   -1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893   -0.1094    1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839    1.3653    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  1
 20  3  1  0
 19  6  1  0
 19  9  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  1
  4 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
M  END


  Mrv1652304282214482D          

 20 23  0  0  1  0            999 V2000
    3.3464    1.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119   -0.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4871   -0.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5217    1.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    0.4690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8376   -0.2353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327   -0.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0575   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0350   -0.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7302    1.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041    1.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    2.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3520    1.3991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0782    0.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629    1.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    2.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761    1.8376    0.0000 O   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  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1CC=C2CCN3CCC4=CC=C(O)C=C4[C@]23C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO2/c1-20-15-5-3-13-7-9-18-8-6-12-2-4-14(19)10-16(12)17(13,18)11-15/h2-4,10,15,19H,5-9,11H2,1H3/t15-,17-/m0/s1

> <INCHI_KEY>
HJMBLPWMTXSDPK-RDJZCZTQSA-N

> <FORMULA>
C17H21NO2

> <MOLECULAR_WEIGHT>
271.36

> <EXACT_MASS>
271.15722892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.37481757286507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,16S)-16-methoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,13-tetraen-4-ol

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
1.6500909811546942

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.831601330272399

> <JCHEM_PKA_STRONGEST_BASIC>
8.905804602481723

> <JCHEM_POLAR_SURFACE_AREA>
32.7

> <JCHEM_REFRACTIVITY>
80.68510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,16S)-16-methoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,13-tetraen-4-ol

> <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       6.247   2.116   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.984   0.764   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.182  -0.551   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.643  -0.514   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.019   0.653   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.707   2.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.366   0.875   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.564  -0.439   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.301  -1.791   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.841  -1.828   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.065  -0.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.059   1.452   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.363   2.044   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.874   3.497   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.388   3.781   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.390   2.612   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.879   1.159   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.904   2.895   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.415   4.348   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.049   3.430   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13   17                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    7                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-3,7-dimethoxy-17-methylmorphin-7-en- 6-one	MeSH
Cucoline	MeSH
Cucoline hydrochloride	MeSH
Cucoline, hydrochloride	MeSH
Cuculine	MeSH
Kukoline	MeSH
Sinomenin hydrochloride	MeSH
Sinomenine	MeSH
Sinomenine a bismethyliodide	MeSH
Sinomenine hydrochloride	MeSH

Chemical Formula

C₁₇H₂₁NO₂

Average Mass

271.3600 Da

Monoisotopic Mass

271.15723 Da

IUPAC Name

(1S,16S)-16-methoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,13-tetraen-4-ol

Traditional Name

(1S,16S)-16-methoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,13-tetraen-4-ol

CAS Registry Number

Not Available

SMILES

CO[C@H]1CC=C2CCN3CCC4=CC=C(O)C=C4[C@]23C1

InChI Identifier

InChI=1S/C17H21NO2/c1-20-15-5-3-13-7-9-18-8-6-12-2-4-14(19)10-16(12)17(13,18)11-15/h2-4,10,15,19H,5-9,11H2,1H3/t15-,17-/m0/s1

InChI Key

HJMBLPWMTXSDPK-RDJZCZTQSA-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 carolinus DC.	Plant	KNApSAcK
Cocculus laurifolius	LOTUS Database	35616633
Cocculus laurifolius DC.	Plant	KNApSAcK
Cocculus orbiculatus	LOTUS Database	35616633
Cocculus trilobus DC.	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
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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	2.65	ALOGPS
logP	1.65	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.69 m³·mol⁻¹	ChemAxon
Polarizability	30.37 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

C00025781

Chemspider ID

10393324

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21769966

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Clementson S, Matheu SA, Rorsted EM, Pedersen H, Jensen AA, Clausen RP, Vital P, Glibstrup E, Jessing M, Kristensen JL: Erythrina Alkaloid Analogues as nAChR Antagonists-A Flexible Platform for Leads in Drug Discovery. J Org Chem. 2021 Jun 18;86(12):8248-8262. doi: 10.1021/acs.joc.1c00707. Epub 2021 Jun 1. [PubMed:34061521 ]
Perol D, Provencal J, Hardy-Bessard AC, Coeffic D, Jacquin JP, Agostini C, Bachelot T, Guastalla JP, Pivot X, Martin JP, Bajard A, Ray-Coquard I: Can treatment with Cocculine improve the control of chemotherapy-induced emesis in early breast cancer patients? A randomized, multi-centered, double-blind, placebo-controlled Phase III trial. BMC Cancer. 2012 Dec 17;12:603. doi: 10.1186/1471-2407-12-603. [PubMed:23244208 ]

Showing NP-Card for (+)-Coculine (NP0067959)

MOL for NP0067959 ((+)-Coculine)

3D MOL for NP0067959 ((+)-Coculine)

3D SDF for NP0067959 ((+)-Coculine)

3D-SDF for NP0067959 ((+)-Coculine)

PDB for NP0067959 ((+)-Coculine)

3D PDB for NP0067959 ((+)-Coculine)

SMILES for NP0067959 ((+)-Coculine)

INCHI for NP0067959 ((+)-Coculine)

Structure for NP0067959 ((+)-Coculine)

3D Structure for NP0067959 ((+)-Coculine)