NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol (NP0251394)

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Record Information

Version

2.0

Created at

2022-09-07 14:34:53 UTC

Updated at

2022-09-07 14:34:53 UTC

NP-MRD ID

NP0251394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol

Description

(2S,3R,4R,5R,6S)-2-methyl-6-(4-{[(1R)-5,6,7-trimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. (2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol is found in Thalictrum fendleri. Based on a literature review very few articles have been published on (2S,3R,4R,5R,6S)-2-methyl-6-(4-{[(1R)-5,6,7-trimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216342D          

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M  END

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  Mrv1652309072216342D          

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 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  1  0  0  0
 22 34  1  0  0  0  0
 34 35  2  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(CCN(C)[C@@H]2CC2=CC=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C=C2)C(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C26H35NO8/c1-14-21(28)22(29)23(30)26(34-14)35-16-8-6-15(7-9-16)12-19-18-13-20(31-3)25(33-5)24(32-4)17(18)10-11-27(19)2/h6-9,13-14,19,21-23,26,28-30H,10-12H2,1-5H3/t14-,19+,21-,22+,23+,26-/m0/s1

> <INCHI_KEY>
YELKLSIRFNKMFQ-BWNGKWBCSA-N

> <FORMULA>
C26H35NO8

> <MOLECULAR_WEIGHT>
489.565

> <EXACT_MASS>
489.236267091

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.539864833465685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-methyl-6-(4-{[(1R)-5,6,7-trimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol

> <JCHEM_LOGP>
2.0296952363333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.268675668467115

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.213649647263793

> <JCHEM_PKA_STRONGEST_BASIC>
8.041277464422015

> <JCHEM_POLAR_SURFACE_AREA>
110.08000000000001

> <JCHEM_REFRACTIVITY>
128.9193

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-methyl-6-(4-{[(1R)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   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       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   35                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24   33                                                  
CONECT   33   32                                                            
CONECT   34   22   35                                                       
CONECT   35   34   19                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₅NO₈

Average Mass

489.5650 Da

Monoisotopic Mass

489.23627 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-methyl-6-(4-{[(1R)-5,6,7-trimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol

Traditional Name

(2S,3R,4R,5R,6S)-2-methyl-6-(4-{[(1R)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(CCN(C)[C@@H]2CC2=CC=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C=C2)C(OC)=C1OC

InChI Identifier

InChI=1S/C26H35NO8/c1-14-21(28)22(29)23(30)26(34-14)35-16-8-6-15(7-9-16)12-19-18-13-20(31-3)25(33-5)24(32-4)17(18)10-11-27(19)2/h6-9,13-14,19,21-23,26,28-30H,10-12H2,1-5H3/t14-,19+,21-,22+,23+,26-/m0/s1

InChI Key

YELKLSIRFNKMFQ-BWNGKWBCSA-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
Thalictrum fendleri	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
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Tetrahydroisoquinoline
Anisole
Phenoxy compound
Phenol ether
Aralkylamine
Alkyl aryl ether
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Oxacycle
Polyol
Azacycle
Acetal
Ether
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Amine
Organooxygen compound
Organopnictogen 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	2.03	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	8.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.92 m³·mol⁻¹	ChemAxon
Polarizability	52.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162894554

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol (NP0251394)

MOL for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

3D MOL for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

3D SDF for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

3D-SDF for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

PDB for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

3D PDB for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

SMILES for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

INCHI for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

Structure for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)

3D Structure for NP0251394 ((2s,3r,4r,5r,6s)-2-methyl-6-(4-{[(1r)-5,6,7-trimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)oxane-3,4,5-triol)