NP-MRD: Showing NP-Card for 4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol (NP0144531)

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Record Information

Version

2.0

Created at

2022-09-01 23:31:57 UTC

Updated at

2022-09-01 23:31:57 UTC

NP-MRD ID

NP0144531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol

Description

Bargustanine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Bargustanine is a very strong basic compound (based on its pKa). Outside of the human body, Bargustanine has been detected, but not quantified in, tea. 4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol is found in Berberis vulgaris. This could make bargustanine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305162D          

 38 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061305162D          

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 10  8  1  0  0  0  0
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 16 12  2  0  0  0  0
 17  8  1  0  0  0  0
 17 13  2  0  0  0  0
 18  5  1  0  0  0  0
 18 11  2  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20  6  1  0  0  0  0
 21 11  1  0  0  0  0
 21 20  2  0  0  0  0
 22 12  1  0  0  0  0
 23 14  1  0  0  0  0
 23 22  2  0  0  0  0
 24 13  1  0  0  0  0
 25 17  1  0  0  0  0
 26 25  1  0  0  0  0
 27 18  1  0  0  0  0
 27 26  1  0  0  0  0
 28 24  2  0  0  0  0
 29 25  2  0  0  0  0
 29 28  1  0  0  0  0
 30  1  1  0  0  0  0
 30  9  1  0  0  0  0
 30 15  1  0  0  0  0
 31  2  1  0  0  0  0
 31 10  1  0  0  0  0
 31 26  1  0  0  0  0
 32 20  1  0  0  0  0
 33 21  1  0  0  0  0
 34 27  1  0  0  0  0
 35 28  1  0  0  0  0
 36  3  1  0  0  0  0
 36 22  1  0  0  0  0
 37  4  1  0  0  0  0
 37 24  1  0  0  0  0
 38 23  1  0  0  0  0
 38 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144531

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=C3C(C(O)C4=CC(O)=C(O)C=C4)N(C)CCC3=CC(OC)=C2O)C=C2CN(C)CCC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H34N2O7/c1-30-9-7-16-12-22(36-3)23(14-19(16)15-30)38-29-25-17(13-24(37-4)28(29)35)8-10-31(2)26(25)27(34)18-5-6-20(32)21(33)11-18/h5-6,11-14,26-27,32-35H,7-10,15H2,1-4H3

> <INCHI_KEY>
AYINLWLMPMZNKE-UHFFFAOYSA-N

> <FORMULA>
C29H34N2O7

> <MOLECULAR_WEIGHT>
522.5895

> <EXACT_MASS>
522.236601452

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
55.40279309538265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy]-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl})methyl]benzene-1,2-diol

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.2109764137396732

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.01299219778703

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3129149502926865

> <JCHEM_PKA_STRONGEST_BASIC>
9.322064967586378

> <JCHEM_POLAR_SURFACE_AREA>
115.09000000000002

> <JCHEM_REFRACTIVITY>
145.1178

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl})methyl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   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  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -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       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      12.003  -5.390   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1   30                                                            
CONECT    2   31                                                            
CONECT    3   36                                                            
CONECT    4   37                                                            
CONECT    5    6   18                                                       
CONECT    6    5   20                                                       
CONECT    7    9   16                                                       
CONECT    8   10   17                                                       
CONECT    9    7   30                                                       
CONECT   10    8   31                                                       
CONECT   11   18   21                                                       
CONECT   12   16   22                                                       
CONECT   13   17   24                                                       
CONECT   14   19   23                                                       
CONECT   15   19   30                                                       
CONECT   16    7   12   19                                                  
CONECT   17    8   13   25                                                  
CONECT   18    5   11   27                                                  
CONECT   19   14   15   16                                                  
CONECT   20    6   21   32                                                  
CONECT   21   11   20   33                                                  
CONECT   22   12   23   36                                                  
CONECT   23   14   22   38                                                  
CONECT   24   13   28   37                                                  
CONECT   25   17   26   29                                                  
CONECT   26   25   27   31                                                  
CONECT   27   18   26   34                                                  
CONECT   28   24   29   35                                                  
CONECT   29   25   28   38                                                  
CONECT   30    1    9   15                                                  
CONECT   31    2   10   26                                                  
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   27                                                            
CONECT   35   28                                                            
CONECT   36    3   22                                                       
CONECT   37    4   24                                                       
CONECT   38   23   29                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄N₂O₇

Average Mass

522.5895 Da

Monoisotopic Mass

522.23660 Da

IUPAC Name

4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy]-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl})methyl]benzene-1,2-diol

Traditional Name

4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl})methyl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=C3C(C(O)C4=CC(O)=C(O)C=C4)N(C)CCC3=CC(OC)=C2O)C=C2CN(C)CCC2=C1

InChI Identifier

InChI=1S/C29H34N2O7/c1-30-9-7-16-12-22(36-3)23(14-19(16)15-30)38-29-25-17(13-24(37-4)28(29)35)8-10-31(2)26(25)27(34)18-5-6-20(32)21(33)11-18/h5-6,11-14,26-27,32-35H,7-10,15H2,1-4H3

InChI Key

AYINLWLMPMZNKE-UHFFFAOYSA-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
Berberis vulgaris	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
Diaryl ether
Tetrahydroisoquinoline
Anisole
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
1,2-aminoalcohol
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Ether
Azacycle
Organonitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Amine
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	2.7	ALOGPS
logP	2.21	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.31	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.12 m³·mol⁻¹	ChemAxon
Polarizability	55.4 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0030505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002376

KNApSAcK ID

C00027521

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

73813822

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol (NP0144531)

MOL for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

3D MOL for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

3D SDF for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

3D-SDF for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

PDB for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

3D PDB for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

SMILES for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

INCHI for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

Structure for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)

3D Structure for NP0144531 (4-[hydroxy({7-hydroxy-6-methoxy-8-[(6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)oxy]-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl})methyl]benzene-1,2-diol)