NP-MRD: Showing NP-Card for (s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol (NP0283020)

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Record Information

Version

2.0

Created at

2022-09-09 10:06:00 UTC

Updated at

2022-09-09 10:06:00 UTC

NP-MRD ID

NP0283020

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol

Description

(S)-{2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}(4-methoxyphenyl)methanol 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)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol is found in Ocotea pulchella. Based on a literature review very few articles have been published on (S)-{2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}(4-methoxyphenyl)methanol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    6.6581    0.0946   -0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146   -0.8199   -0.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2934   -0.3899   -0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2538   -1.2797   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9314   -0.8705   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371    0.3927    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2324    0.8373    0.6331 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2562    1.6924    1.7637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063   -0.2725    0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3540   -1.3899    1.5172 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2202   -2.3964    1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -2.3410    1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9047   -1.2257    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2024   -1.1653    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6351   -0.0692   -0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7669    0.9685   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    0.9002   -0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -0.1962    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4064    1.9895   -1.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7998    1.7125   -1.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8321    0.3253   -1.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869    1.2627    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    0.8857    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6524    0.9659   -0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6437   -0.4131   -0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432    0.5295    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712   -2.2871   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490   -1.5872   -0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805    1.4366   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239    1.2516    2.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -3.3089    2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265   -3.1430    1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8897   -1.9770    0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    1.7490   -0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2410    2.0058   -2.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2333    2.3109   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936    2.2583    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8354    1.5635    0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 22  1  0
 22 23  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 18  1  0
 18 17  2  0
 17 16  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 23  3  1  0
 10  9  2  0
 13 18  1  0
 15 16  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 22 37  1  0
 23 38  1  0
  7 29  1  6
  8 30  1  0
 17 34  1  0
 20 35  1  0
 20 36  1  0
 14 33  1  0
 12 32  1  0
 11 31  1  0
M  END


  Mrv1652309092212062D          

 23 26  0  0  1  0            999 V2000
   -1.4289   -4.9500    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
   -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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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
    0.7145   -1.2375    0.0000 N   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    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
    2.8579    0.0000    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
    3.5724   -1.2375    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   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
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283020

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@H](O)C1=C2C=C3OCOC3=CC2=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO4/c1-21-13-4-2-11(3-5-13)18(20)17-14-9-16-15(22-10-23-16)8-12(14)6-7-19-17/h2-9,18,20H,10H2,1H3/t18-/m0/s1

> <INCHI_KEY>
NOIDDJJSLONVDW-SFHVURJKSA-N

> <FORMULA>
C18H15NO4

> <MOLECULAR_WEIGHT>
309.321

> <EXACT_MASS>
309.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.0443654822391

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(S)-{2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}(4-methoxyphenyl)methanol

> <JCHEM_LOGP>
2.4611638756666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.261237303457673

> <JCHEM_PKA_STRONGEST_BASIC>
5.247602524274648

> <JCHEM_POLAR_SURFACE_AREA>
60.81

> <JCHEM_REFRACTIVITY>
83.23300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(S)-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17    9   13                                                  
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15                                                       
CONECT   22    6   23                                                       
CONECT   23   22    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₅NO₄

Average Mass

309.3210 Da

Monoisotopic Mass

309.10011 Da

IUPAC Name

(S)-{2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}(4-methoxyphenyl)methanol

Traditional Name

(S)-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@H](O)C1=C2C=C3OCOC3=CC2=CC=N1

InChI Identifier

InChI=1S/C18H15NO4/c1-21-13-4-2-11(3-5-13)18(20)17-14-9-16-15(22-10-23-16)8-12(14)6-7-19-17/h2-9,18,20H,10H2,1H3/t18-/m0/s1

InChI Key

NOIDDJJSLONVDW-SFHVURJKSA-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
Ocotea pulchella	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
Benzodioxole
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Secondary alcohol
Ether
Acetal
Oxacycle
Azacycle
Aromatic alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen 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	2.46	ChemAxon
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	5.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	32.04 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

28944894

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162981118

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol (NP0283020)

MOL for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

3D MOL for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

3D SDF for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

3D-SDF for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

PDB for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

3D PDB for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

SMILES for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

INCHI for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

Structure for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)

3D Structure for NP0283020 ((s)-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl(4-methoxyphenyl)methanol)