NP-MRD: Showing NP-Card for Narcotoline (NP0051007)

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Record Information

Version

2.0

Created at

2022-04-27 22:27:36 UTC

Updated at

2022-04-27 22:27:37 UTC

NP-MRD ID

NP0051007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Narcotoline

Description

Narcotoline belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide. Narcotoline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Narcotoline is found in Papaver somniferum . Narcotoline was first documented in 2014 (PMID: 24324259). Based on a literature review a small amount of articles have been published on Narcotoline (PMID: 29723437) (PMID: 27378283) (PMID: 29677437) (PMID: 25485687).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200272D          

 29 33  0  0  1  0            999 V2000
   -2.5085    1.8030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9565    2.4160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2114    3.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0184    3.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5704    2.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    1.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8675    1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6745    1.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294    2.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774    2.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544    2.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0094    1.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419    1.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6126    0.5768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    2.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536    1.0183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7385    0.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -0.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -1.1012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889   -0.0616    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
  7 14  1  0  0  0  0
  2 15  1  0  0  0  0
  1 16  1  1  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
    4.6021    1.6954   -2.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5907    0.7773   -1.4326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099    0.6730   -0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.4323   -0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466    1.3003   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    0.4337    0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1798   -0.3257    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3219   -0.1992    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642   -0.9564    0.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259   -2.2087    0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232   -1.1421    2.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6606   -1.9617    2.8048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375   -0.8972    2.7015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368    0.1089    1.8333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2015   -0.6088    1.1866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1303    0.1837    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8706   -0.5079   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811    0.1489   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9896    1.5139   -1.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611    2.1828   -0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203    1.5264    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200    2.2541    1.5151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6135    3.5329   -0.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    3.6091   -0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8134    2.4293   -1.7842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6473   -1.9422   -0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095   -2.0867   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5864   -1.7439    0.5194 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -2.9350    1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2819    2.6886   -2.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8343    1.4518   -3.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5972    1.8582   -2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3415    2.1253   -1.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.9192   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5479   -2.6747    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   -2.8964    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1572   -2.1527   -0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287    0.9642    2.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -1.0956    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344   -0.4134   -2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730    3.2415    1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8365    4.4655   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6905    3.5619   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0023   -2.3510   -1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312   -2.4885    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117   -3.1514   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -1.5049   -1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3321   -3.6759    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8839   -2.7043    2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3705   -3.4538    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 14 15  1  0
 15 28  1  0
 28 29  1  0
 28 27  1  0
 27 26  1  0
 26 17  1  0
 17 16  2  0
 16 21  1  0
 21 22  1  0
 21 20  2  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 19  1  0
 19 18  2  0
  4  3  1  0
 16 15  1  0
 19 20  1  0
 11  7  1  0
 18 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  5 34  1  0
  4 33  1  0
 14 38  1  1
 15 39  1  1
 29 48  1  0
 29 49  1  0
 29 50  1  0
 27 46  1  0
 27 47  1  0
 26 44  1  0
 26 45  1  0
 22 41  1  0
 24 42  1  0
 24 43  1  0
 18 40  1  0
M  END


  Mrv1652304282200272D          

 29 33  0  0  1  0            999 V2000
   -2.5085    1.8030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9565    2.4160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2114    3.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0184    3.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5704    2.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    1.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8675    1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6745    1.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294    2.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774    2.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544    2.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0094    1.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419    1.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6126    0.5768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    2.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536    1.0183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7385    0.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -0.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085   -1.1012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889   -0.0616    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
  7 14  1  0  0  0  0
  2 15  1  0  0  0  0
  1 16  1  1  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C=C1)[C@H](OC2=O)[C@@H]1N(C)CCC2=C1C(O)=C1OCOC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1

> <INCHI_KEY>
LMGZCSKYOKDBES-AEFFLSMTSA-N

> <FORMULA>
C21H21NO7

> <MOLECULAR_WEIGHT>
399.399

> <EXACT_MASS>
399.13180202

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.084910295995854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-[(5R)-4-hydroxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.316170277394985

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.187983371587062

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.076430271113708

> <JCHEM_PKA_STRONGEST_BASIC>
7.250082067169377

> <JCHEM_POLAR_SURFACE_AREA>
86.69000000000003

> <JCHEM_REFRACTIVITY>
102.59379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
narcotoline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.683   3.366   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -3.652   4.510   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -4.128   5.975   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.634   6.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.665   5.150   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.189   3.686   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.219   2.541   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.726   2.861   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.202   4.326   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.171   5.471   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -10.742   4.326   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -11.217   2.861   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -9.972   1.956   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -6.743   1.077   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.146   4.190   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.207   1.901   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.112   0.655   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.207  -0.591   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.683  -2.056   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.742  -0.115   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.742   1.425   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.408   2.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.075   1.425   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.075  -0.115   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.408  -0.885   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.408  -2.425   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.742  -3.195   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.259  -0.885   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.593  -0.115   0.000  0.00  0.00           C+0
CONECT    1    2    6   16                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    7                                                            
CONECT   15    2                                                            
CONECT   16    1   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   24   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Narcotoline hydrochloride	MeSH

Chemical Formula

C₂₁H₂₁NO₇

Average Mass

399.3990 Da

Monoisotopic Mass

399.13180 Da

IUPAC Name

(3S)-3-[(5R)-4-hydroxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one

Traditional Name

narcotoline

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C=C1)[C@H](OC2=O)[C@@H]1N(C)CCC2=C1C(O)=C1OCOC1=C2

InChI Identifier

InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1

InChI Key

LMGZCSKYOKDBES-AEFFLSMTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 somniferum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Phthalide isoquinolines

Sub Class

Not Available

Direct Parent

Phthalide isoquinolines

Alternative Parents

Substituents

Phthalide isoquinoline
Phthalide
Isobenzofuranone
Benzofuranone
Tetrahydroisoquinoline
Benzodioxole
Isocoumaran
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Benzenoid
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Tertiary amine
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Ether
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:7482 )
Isoquinoline alkaloids (C09593 )

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	1.98	ALOGPS
logP	2.32	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	7.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	40.08 Å³	ChemAxon
Number of Rings	5	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

C00001892

Chemspider ID

390785

KEGG Compound ID

C09593

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Narcotoline

METLIN ID

Not Available

PubChem Compound

442330

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dang TT, Facchini PJ: CYP82Y1 is N-methylcanadine 1-hydroxylase, a key noscapine biosynthetic enzyme in opium poppy. J Biol Chem. 2014 Jan 24;289(4):2013-26. doi: 10.1074/jbc.M113.505099. Epub 2013 Dec 9. [PubMed:24324259 ]
Park MR, Chen X, Lang DE, Ng KKS, Facchini PJ: Heterodimeric O-methyltransferases involved in the biosynthesis of noscapine in opium poppy. Plant J. 2018 Jul;95(2):252-267. doi: 10.1111/tpj.13947. Epub 2018 Jun 8. [PubMed:29723437 ]
Li Y, Smolke CD: Engineering biosynthesis of the anticancer alkaloid noscapine in yeast. Nat Commun. 2016 Jul 5;7:12137. doi: 10.1038/ncomms12137. [PubMed:27378283 ]
Kwiecien-Obara E, Szponar J, Krajewska A, Witkowska A, Radoniewicz A, Szponar M: [Morphine (obtained from poppy seeds) and dextrometorfan poisoning- a case report]. Przegl Lek. 2016;73(8):596-8. [PubMed:29677437 ]
Dang TT, Chen X, Facchini PJ: Acetylation serves as a protective group in noscapine biosynthesis in opium poppy. Nat Chem Biol. 2015 Feb;11(2):104-6. doi: 10.1038/nchembio.1717. Epub 2014 Dec 8. [PubMed:25485687 ]

Showing NP-Card for Narcotoline (NP0051007)

MOL for NP0051007 (Narcotoline)

3D MOL for NP0051007 (Narcotoline)

3D SDF for NP0051007 (Narcotoline)

3D-SDF for NP0051007 (Narcotoline)

PDB for NP0051007 (Narcotoline)

3D PDB for NP0051007 (Narcotoline)

SMILES for NP0051007 (Narcotoline)

INCHI for NP0051007 (Narcotoline)

Structure for NP0051007 (Narcotoline)

3D Structure for NP0051007 (Narcotoline)