NP-MRD: Showing NP-Card for [2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol (NP0155853)

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Record Information

Version

2.0

Created at

2022-09-02 12:58:58 UTC

Updated at

2022-09-02 12:58:58 UTC

NP-MRD ID

NP0155853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol

Description

[2-(Hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})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. [2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol is found in Papaver pseudo-orientale. [2-(Hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241518052D          

 30 33  0  0  0  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  0  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
    0.0000   -1.6500    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    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
    4.3570   -0.1576    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   -1.4924    0.0000 O   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
    2.8579   -2.4750    0.0000 O   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
    2.1434   -1.2375    0.0000 C   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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   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
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    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  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  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  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
  9 24  1  0  0  0  0
 14 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.9988    0.1063   -2.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3786    0.0757   -0.9108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0383   -0.0901   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2604   -0.2392   -1.8744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8943   -0.4112   -1.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.4298   -0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998   -0.7606   -0.3392 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2879   -1.9624   -1.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    0.2838   -0.8085 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3014    0.3776   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812    1.7102    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461    2.0019    0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6102    0.9688    1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225   -0.3313    1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0332   -0.6637    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032   -1.9803    0.2768 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2762   -3.0341    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1825   -1.1609    1.7179 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9503   -0.3608    2.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957    0.9526    2.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7971    2.7533   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3303    2.3830   -1.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2303    0.9095   -1.9651 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336    0.6711   -3.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903   -0.2825    0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038   -0.2534    2.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2665   -0.0753    3.0501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459   -0.1104    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2266    0.0590    1.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901   -1.0000    2.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3492   -0.8718   -2.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085    0.6178   -2.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9143    0.7678   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7027   -0.2420   -2.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639   -0.5588   -2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969   -1.0247    0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -1.9019   -1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253    1.2227   -0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0736    3.0589    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -2.8275    1.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8211   -3.7552    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1214   -3.6778    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5344   -0.4065    3.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929   -0.6680    2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069    3.7078   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    3.0586    0.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047    2.8153   -1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602    2.7710   -2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0712    1.0478   -3.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -0.4117   -3.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6399    1.2033   -4.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0277   -1.3197    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862    0.3471    2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1009    0.8221    3.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9233   -0.6515    3.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -1.9081    2.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8006   -1.3218    2.0124 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  7  1  0
  7  8  1  0
  7  9  1  0
  9 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 21 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 10  2  0
  6 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 10  9  1  0
 10 11  1  0
 20 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  7 36  1  1
  8 37  1  0
  9 38  1  1
 24 49  1  0
 24 50  1  0
 24 51  1  0
 22 47  1  0
 22 48  1  0
 21 45  1  0
 21 46  1  0
 12 39  1  0
 19 43  1  0
 19 44  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
M  END


  Mrv1533004241518052D          

 30 33  0  0  0  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  0  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
    0.0000   -1.6500    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    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
    4.3570   -0.1576    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   -1.4924    0.0000 O   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
    2.8579   -2.4750    0.0000 O   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
    2.1434   -1.2375    0.0000 C   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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   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
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    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  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  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  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
  9 24  1  0  0  0  0
 14 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C(O)C2N(C)CCC3=CC4=C(OCO4)C(OC)=C23)C(CO)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO7/c1-23-8-7-12-9-16-21(30-11-29-16)22(28-4)17(12)18(23)19(25)13-5-6-15(26-2)20(27-3)14(13)10-24/h5-6,9,18-19,24-25H,7-8,10-11H2,1-4H3

> <INCHI_KEY>
BHLLOBXLOWXZDQ-UHFFFAOYSA-N

> <FORMULA>
C22H27NO7

> <MOLECULAR_WEIGHT>
417.458

> <EXACT_MASS>
417.178752213

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.75020050478799

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.491306238

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.65295980037978

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.567162720299223

> <JCHEM_PKA_STRONGEST_BASIC>
6.904566460915812

> <JCHEM_POLAR_SURFACE_AREA>
89.85000000000002

> <JCHEM_REFRACTIVITY>
110.12799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   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  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.038  -1.540   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   24                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21    9   14                                                  
CONECT   25    6   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
alpha-Narcotinediol	MeSH

Chemical Formula

C₂₂H₂₇NO₇

Average Mass

417.4580 Da

Monoisotopic Mass

417.17875 Da

IUPAC Name

[2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol

Traditional Name

[2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C(O)C2N(C)CCC3=CC4=C(OCO4)C(OC)=C23)C(CO)=C1OC

InChI Identifier

InChI=1S/C22H27NO7/c1-23-8-7-12-9-16-21(30-11-29-16)22(28-4)17(12)18(23)19(25)13-5-6-15(26-2)20(27-3)14(13)10-24/h5-6,9,18-19,24-25H,7-8,10-11H2,1-4H3

InChI Key

BHLLOBXLOWXZDQ-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
Papaver pseudo-orientale	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
Dimethoxybenzene
O-dimethoxybenzene
Benzodioxole
Anisole
Methoxybenzene
Benzyl alcohol
Phenol ether
Phenoxy compound
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
1,2-aminoalcohol
Acetal
Oxacycle
Azacycle
Ether
Aromatic alcohol
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Amine
Organic oxygen compound
Alcohol
Primary alcohol
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	1.68	ALOGPS
logP	1.49	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.57	ChemAxon
pKa (Strongest Basic)	6.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.85 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	110.13 m³·mol⁻¹	ChemAxon
Polarizability	43.75 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	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

98447

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol (NP0155853)

MOL for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

3D MOL for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

3D SDF for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

3D-SDF for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

PDB for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

3D PDB for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

SMILES for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

INCHI for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

Structure for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)

3D Structure for NP0155853 ([2-(hydroxymethyl)-3,4-dimethoxyphenyl]({4-methoxy-6-methyl-2h,5h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl})methanol)