NP-MRD: Showing NP-Card for (s)-n-methylcoclaurine (NP0221136)

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Record Information

Version

2.0

Created at

2022-09-05 22:37:43 UTC

Updated at

2022-09-05 22:37:44 UTC

NP-MRD ID

NP0221136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(s)-n-methylcoclaurine

Description

(S)-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 (S)-N-Methylcoclaurine is a very strong basic compound (based on its pKa) (S)-N-Methylcoclaurine exists in all living organisms, ranging from bacteria to humans. (s)-n-methylcoclaurine is found in Aristolochia gigantea, Clematis parviloba, Cocculus laurifolius, Delphinium pentagynum, Glaucium fimbrilligerum, Gnetum montanum, Mus musculus, Romneya coulteri, Stephania excentrica, Stephania pierrei and Xylopia parviflora. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    4.1205    2.8928    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4685    2.7208   -0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632    1.6814   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2672    0.7852    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689   -0.2405    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -0.4154   -1.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    0.4684   -2.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9220    1.5079   -1.8701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741    2.3655   -2.9326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -1.5140   -1.2202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6226   -0.9597   -1.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.1255   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9630    1.2379   -0.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    1.9863    0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119    1.4009    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7266    2.1698    2.7235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189    0.0583    1.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962   -0.6946    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -2.5328   -0.2590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -3.6718   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -2.5333    0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910   -1.1848    1.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9621    2.1798    0.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4315    2.8113    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5647    3.9175    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    0.9051    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    0.3824   -3.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329    3.1192   -2.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692   -1.9906   -2.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533   -0.2922   -2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070   -1.7729   -1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943    1.7735   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    3.0659    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5670    3.1522    2.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9948   -0.4172    2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -1.7606    0.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -3.7811    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -3.8268   -1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -4.5764   -0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -3.1043    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2723   -3.1118    1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240   -0.7310    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0060   -1.3449    1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6 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
 10 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22  5  1  0
  5  4  2  0
  4  3  1  0
  5  6  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  9 28  1  0
  7 27  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
  4 26  1  0
M  END


  Mrv0541 05161317532D          

 22 24  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    0.7145   -0.4125    0.0000 C   0  0  0  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
    2.8579    0.0000    0.0000 C   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
    2.1434   -2.8875    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  6  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  2  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 21 17  1  0  0  0  0
 22  2  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1

> <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-/m0/s1

> <INCHI_KEY>
BOKVLBSSPUTWLV-INIZCTEOSA-N

> <FORMULA>
C18H21NO3

> <MOLECULAR_WEIGHT>
299.3642

> <EXACT_MASS>
299.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.249873541988606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.1348029627290432

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.478747372643047

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.87366736995705

> <JCHEM_PKA_STRONGEST_BASIC>
8.196163455842322

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
87.3731

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-N-methylcoclaurine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   22                                                            
CONECT    3    5   12                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   14                                                       
CONECT    7    8   13                                                       
CONECT    8    7   19                                                       
CONECT    9   12   16                                                       
CONECT   10   13   18                                                       
CONECT   11   15   17                                                       
CONECT   12    3    4    9                                                  
CONECT   13    7   10   15                                                  
CONECT   14    5    6   20                                                  
CONECT   15   11   13   16                                                  
CONECT   16    9   15   19                                                  
CONECT   17   11   18   21                                                  
CONECT   18   10   17   22                                                  
CONECT   19    1    8   16                                                  
CONECT   20   14                                                            
CONECT   21   17                                                            
CONECT   22    2   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₈H₂₁NO₃

Average Mass

299.3642 Da

Monoisotopic Mass

299.15214 Da

IUPAC Name

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

Traditional Name

(S)-N-methylcoclaurine

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1

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-/m0/s1

InChI Key

BOKVLBSSPUTWLV-INIZCTEOSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aristolochia gigantea	LOTUS Database	35616633
Clematis parviloba	LOTUS Database	35616633
Cocculus laurifolius	LOTUS Database	35616633
Delphinium pentagynum	LOTUS Database	35616633
Glaucium fimbrilligerum	LOTUS Database	35616633
Gnetum montanum	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Romneya coulteri	LOTUS Database	35616633
Stephania excentrica	LOTUS Database	35616633
Stephania pierrei	LOTUS Database	35616633
Xylopia parviflora	LOTUS Database	35616633

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:17041 )
Isoquinoline alkaloids (C05176 )

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	3.13	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	8.2	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	33.25 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

HMDB0060319

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025268

Chemspider ID

Not Available

KEGG Compound ID

C05176

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440584

PDB ID

Not Available

ChEBI ID

17041

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (s)-n-methylcoclaurine (NP0221136)

MOL for NP0221136 ((s)-n-methylcoclaurine)

3D MOL for NP0221136 ((s)-n-methylcoclaurine)

3D SDF for NP0221136 ((s)-n-methylcoclaurine)

3D-SDF for NP0221136 ((s)-n-methylcoclaurine)

PDB for NP0221136 ((s)-n-methylcoclaurine)

3D PDB for NP0221136 ((s)-n-methylcoclaurine)

SMILES for NP0221136 ((s)-n-methylcoclaurine)

INCHI for NP0221136 ((s)-n-methylcoclaurine)

Structure for NP0221136 ((s)-n-methylcoclaurine)

3D Structure for NP0221136 ((s)-n-methylcoclaurine)