NP-MRD: Showing NP-Card for 1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol (NP0191077)

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Record Information

Version

2.0

Created at

2022-09-04 07:53:39 UTC

Updated at

2022-09-04 07:53:39 UTC

NP-MRD ID

NP0191077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

Description

Juzirine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Juzirine is a very strong basic compound (based on its pKa). Outside of the human body, Juzirine has been detected, but not quantified in, fruits. 1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol is found in Xylopia parviflora and Ziziphus jujuba. This could make juzirine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.1498    1.4827   -0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1046    1.7379    0.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253    0.8676    0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879   -0.2520   -0.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7970   -1.0928   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6665   -2.2207   -1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844   -3.0605   -1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699   -2.7775   -0.3944 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014   -1.6742    0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237   -1.3995    1.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337   -0.4584    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110    0.8211    1.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700    1.6823    0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    1.2460   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542    2.0637   -0.8961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360   -0.0501   -0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2817   -0.8587   -0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805   -0.8375    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260    0.2915    1.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0226    1.1354    1.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804    2.2533    1.8543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584    1.6795   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4545    0.3952   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0051    2.1210   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609   -0.4826   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4761   -2.4103   -2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -3.9239   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1060   -1.0504    2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9745   -2.3627    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0017    1.2082    2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6721    2.6878    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3147    2.0883   -0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8943   -0.3559   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789   -1.8647   -0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.5095    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920    2.8613    1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  2  0
 20 21  1  0
 20 19  1  0
 19 18  2  0
 18  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 18  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 36  1  0
 19 35  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
  7 27  1  0
  6 26  1  0
  4 25  1  0
M  END


  Mrv0541 05061307282D          

 21 23  0  0  0  0            999 V2000
    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  0  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
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 11  2  2  0  0  0  0
 11  3  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18  7  1  0  0  0  0
 18 15  2  0  0  0  0
 19 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21  1  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(CC3=CC=C(O)C=C3)=NC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-7,9-10,19-20H,8H2,1H3

> <INCHI_KEY>
XUCRLUHFLBPVRO-UHFFFAOYSA-N

> <FORMULA>
C17H15NO3

> <MOLECULAR_WEIGHT>
281.3059

> <EXACT_MASS>
281.105193351

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.443026747129913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.945958225333333

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.060440294399942

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.139594416111942

> <JCHEM_PKA_STRONGEST_BASIC>
6.0464121044877706

> <JCHEM_POLAR_SURFACE_AREA>
62.58000000000001

> <JCHEM_REFRACTIVITY>
80.0897

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

> <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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    4   11                                                       
CONECT    3    5   11                                                       
CONECT    4    2   13                                                       
CONECT    5    3   13                                                       
CONECT    6    7   12                                                       
CONECT    7    6   18                                                       
CONECT    8   11   15                                                       
CONECT    9   12   17                                                       
CONECT   10   14   16                                                       
CONECT   11    2    3    8                                                  
CONECT   12    6    9   14                                                  
CONECT   13    4    5   19                                                  
CONECT   14   10   12   15                                                  
CONECT   15    8   14   18                                                  
CONECT   16   10   17   20                                                  
CONECT   17    9   16   21                                                  
CONECT   18    7   15                                                       
CONECT   19   13                                                            
CONECT   20   16                                                            
CONECT   21    1   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
1-((4-Hydroxyphenyl)methyl)-6-methoxy-7-isoquinolinol	HMDB
7-Hydroxy-1-(4-hydroxybenzyl)-6-methoxyisoquinoline	HMDB
Yuzirine	HMDB
Juzirine	MeSH

Chemical Formula

C₁₇H₁₅NO₃

Average Mass

281.3059 Da

Monoisotopic Mass

281.10519 Da

IUPAC Name

1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

Traditional Name

1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(CC3=CC=C(O)C=C3)=NC=CC2=C1

InChI Identifier

InChI=1S/C17H15NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-7,9-10,19-20H,8H2,1H3

InChI Key

XUCRLUHFLBPVRO-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
Xylopia parviflora	LOTUS Database	35616633
Ziziphus jujuba	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
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Azacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
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	2.96	ALOGPS
logP	2.95	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	6.05	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.58 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.09 m³·mol⁻¹	ChemAxon
Polarizability	29.44 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

HMDB0033954

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012170

KNApSAcK ID

C00035166

Chemspider ID

2342227

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3085285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol (NP0191077)

MOL for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

3D MOL for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

3D SDF for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

3D-SDF for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

PDB for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

3D PDB for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

SMILES for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

INCHI for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

Structure for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)

3D Structure for NP0191077 (1-[(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol)