NP-MRD: Showing NP-Card for (-)-N-Methylcoclaurine (NP0067800)

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Record Information

Version

2.0

Created at

2022-04-28 12:38:46 UTC

Updated at

2022-04-28 12:38:46 UTC

NP-MRD ID

NP0067800

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-N-Methylcoclaurine

Description

(R)-N-methylcoclaurine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (R)-N-methylcoclaurine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (-)-N-Methylcoclaurine is found in Cyclea barbata Miers , Cyclea peltata Diels , Glaucium leiocarpum, Nelumbo nucifera, Roemeria refracta, Xylopia pancheri, Xylopia parviflora and Xylopia vieillardi. (-)-N-Methylcoclaurine was first documented in 2020 (PMID: 31865477). Based on a literature review very few articles have been published on (R)-N-methylcoclaurine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282214382D          

 22 24  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2 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
  1 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 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
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067800

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)[C@@H](CC1=CC=C(O)C=C1)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m1/s1

> <INCHI_KEY>
BOKVLBSSPUTWLV-MRXNPFEDSA-N

> <FORMULA>
C18H21NO3

> <MOLECULAR_WEIGHT>
299.37

> <EXACT_MASS>
299.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.33583412707052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.1465105410333543

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.47756485467126

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.871975490197116

> <JCHEM_PKA_STRONGEST_BASIC>
8.114347853574051

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
87.37310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-1betah-coclaurine

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8                                                            
CONECT   10    2   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12    1   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(R)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol	ChEBI

Chemical Formula

C₁₈H₂₁NO₃

Average Mass

299.3700 Da

Monoisotopic Mass

299.15214 Da

IUPAC Name

(1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

Traditional Name

2-methyl-1betah-coclaurine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)[C@@H](CC1=CC=C(O)C=C1)N(C)CC2

InChI Identifier

InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m1/s1

InChI Key

BOKVLBSSPUTWLV-MRXNPFEDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cyclea barbata	Plant	KNApSAcK
Cyclea peltata Diels	Plant	KNApSAcK
Glaucium leiocarpum	LOTUS Database	35616633
Nelumbo nucifera	LOTUS Database	35616633
Roemeria refracta	LOTUS Database	35616633
Xylopia pancheri	Plant	KNApSAcK
Xylopia parviflora	Plant	KNApSAcK
Xylopia vieillardi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-methylcoclaurine (CHEBI:16387 )
Isoquinoline alkaloids (C05243 )

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	2.69	ALOGPS
logP	3.15	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	8.11	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.37 m³·mol⁻¹	ChemAxon
Polarizability	33.34 Å³	ChemAxon
Number of Rings	3	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

C00025619

Chemspider ID

389493

KEGG Compound ID

C05243

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440595

PDB ID

Not Available

ChEBI ID

16387

Good Scents ID

Not Available

References

General References

Zhao W, Shen C, Zhu J, Ou C, Liu M, Dai W, Liu X, Liu J: Identification and characterization of methyltransferases involved in benzylisoquinoline alkaloids biosynthesis from Stephania intermedia. Biotechnol Lett. 2020 Mar;42(3):461-469. doi: 10.1007/s10529-019-02785-0. Epub 2019 Dec 21. [PubMed:31865477 ]

Showing NP-Card for (-)-N-Methylcoclaurine (NP0067800)

MOL for NP0067800 ((-)-N-Methylcoclaurine)

3D MOL for NP0067800 ((-)-N-Methylcoclaurine)

3D SDF for NP0067800 ((-)-N-Methylcoclaurine)

3D-SDF for NP0067800 ((-)-N-Methylcoclaurine)

PDB for NP0067800 ((-)-N-Methylcoclaurine)

3D PDB for NP0067800 ((-)-N-Methylcoclaurine)

SMILES for NP0067800 ((-)-N-Methylcoclaurine)

INCHI for NP0067800 ((-)-N-Methylcoclaurine)

Structure for NP0067800 ((-)-N-Methylcoclaurine)

3D Structure for NP0067800 ((-)-N-Methylcoclaurine)