NP-MRD: Showing NP-Card for alpha-Narcotine (NP0051006)

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Record Information

Version

2.0

Created at

2022-04-27 22:27:34 UTC

Updated at

2022-04-27 22:27:34 UTC

NP-MRD ID

NP0051006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Narcotine

Description

(-)-Alpha-Narcotine, also known as capval or noscapina, 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 (-)-alpha-Narcotine is a very strong basic compound (based on its pKa) (-)-alpha-Narcotine is a bitter tasting compound. Outside of the human body, (-)-alpha-Narcotine has been detected, but not quantified in, opium poppies. alpha-Narcotine is found in Apis cerana, Citrus sinensis , Corydalis heterocarpa, Corydalis solida, Papaver commutatum, Papaver pseudo-orientale, Papaver rhoeas , Papaver rhopalothece and Papaver somniferum . alpha-Narcotine was first documented in 2012 (PMID: 22079300). This could make (-)-alpha-narcotine a potential biomarker for the consumption of these foods (PMID: 22546556) (PMID: 22653730) (PMID: 22671862) (PMID: 22733149).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241219522D          

 32 36  0  0  0  0            999 V2000
    2.5459   -2.7015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2910   -3.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -2.2166    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8785   -1.3916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5929   -0.9791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3074   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785    0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1640   -0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495    0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496    0.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345   -0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496   -1.2340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495   -2.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -2.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1640   -0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743   -4.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110   -2.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -2.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857   -3.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -4.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660   -3.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -4.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8930   -5.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4977   -4.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2841   -5.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -3.0416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -0.5666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2 26  1  0  0  0  0
 21  3  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
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 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 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
 16 19  2  0  0  0  0
  4 19  1  0  0  0  0
  9 19  1  0  0  0  0
  2 20  2  0  0  0  0
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 21 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 31  1  6  0  0  0
  4 32  1  6  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    4.9938    1.8001   -1.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8457    0.8361   -0.9952 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    0.5529   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4601    1.2203   -0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    0.9229   -0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -0.0296    0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773   -0.6913    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5045   -0.4090    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6738   -1.0664    0.9412 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4261   -0.4651    2.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9765   -1.6674    2.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8207   -2.4364    2.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -1.5843    2.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0328   -0.5349    1.6120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1155   -1.1827    0.9374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0568   -0.3657    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7451   -0.9842   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -0.2618   -1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8461    1.0851   -1.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1575    1.6705   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675    0.9490    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755    1.7162    1.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4313    1.8310    2.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    3.0091   -0.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6336    3.2207   -1.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565    2.0254   -2.0586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -2.4318   -1.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225   -3.1639   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -2.3363    0.1387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412   -1.9585   -1.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0126    1.7361   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4406   -0.8609    2.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9427   -0.6455    2.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5035    0.6419    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2540    0.2128    2.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210   -1.6771    1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777   -0.7180   -2.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4924    0.8079    3.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    2.5385    3.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4547    2.2139    2.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4760    4.0550   -1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6159    3.2888   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589   -2.8941   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894   -2.6077   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347   -3.2616    0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5302   -4.1488   -0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -2.0784   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791   -1.0249   -1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122   -2.7548   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 11  1  0
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  7  6  2  0
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  5  4  2  0
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  2  1  1  0
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 29 30  1  0
 29 28  1  0
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 27 17  1  0
 17 18  2  0
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 19 20  2  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 16  2  0
  6 14  1  0
 16 15  1  0
  8  7  1  0
 16 17  1  0
 26 19  1  0
 14 39  1  1
  5 35  1  0
  4 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 15 40  1  1
 30 51  1  0
 30 52  1  0
 30 53  1  0
 28 49  1  0
 28 50  1  0
 27 47  1  0
 27 48  1  0
 18 41  1  0
 25 45  1  0
 25 46  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
M  END


  Mrv0541 02241219522D          

 32 36  0  0  0  0            999 V2000
    2.5459   -2.7015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2910   -3.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -2.2166    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8785   -1.3916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5929   -0.9791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3074   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785    0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1640   -0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495    0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496    0.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345   -0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496   -1.2340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1640   -0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743   -4.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110   -2.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8785   -0.5666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2 26  1  0  0  0  0
 21  3  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 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
 16 19  2  0  0  0  0
  4 19  1  0  0  0  0
  9 19  1  0  0  0  0
  2 20  2  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
 25 26  1  0  0  0  0
 21 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 31  1  6  0  0  0
  4 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

> <INCHI_KEY>
AKNNEGZIBPJZJG-MSOLQXFVSA-N

> <FORMULA>
C22H23NO7

> <MOLECULAR_WEIGHT>
413.4205

> <EXACT_MASS>
413.147452095

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
42.1875768582998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.580710038

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.593243441303297

> <JCHEM_PKA_STRONGEST_BASIC>
6.444144933804225

> <JCHEM_POLAR_SURFACE_AREA>
75.69000000000001

> <JCHEM_REFRACTIVITY>
107.0761

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
noscapine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.752  -5.043   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.277  -6.507   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.507  -4.138   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.507  -2.598   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.840  -1.828   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.174  -2.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.840  -0.288   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.507   0.482   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.173  -0.288   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.839   0.482   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.494  -0.288   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.959   0.188   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.864  -1.058   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.959  -2.303   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.494  -1.828   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.839  -2.598   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.839  -4.138   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.494  -4.908   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.173  -1.828   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.365  -7.596   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.261  -5.043   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.850  -4.621   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.239  -5.710   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.160  -7.198   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.648  -7.596   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.737  -6.507   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.046  -9.084   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.534  -9.482   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.929  -8.287   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.530  -9.774   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       3.507  -5.678   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.507  -1.058   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1   26   20                                                  
CONECT    3   21    1    4   31                                             
CONECT    4    3    5   19   32                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16    4    9                                                  
CONECT   20    2                                                            
CONECT   21    3   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26    2   25   21                                                  
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(-)-Narcotine	ChEBI
alpha-Narcotine	ChEBI
Noscapina	ChEBI
Noscapine	ChEBI
Noscapinum	ChEBI
a-Narcotine	Generator
Α-narcotine	Generator
(-)-a-Narcotine	Generator
(-)-Α-narcotine	Generator
Capval	HMDB
Coscopin	HMDB
L-alpha-Narcotine	HMDB
Longatin	HMDB
Lyobex	HMDB
Methoxyhydrastine	HMDB
Narcompren	HMDB
Narcosine	HMDB
Narcotin	HMDB
Narcotussin	HMDB
Narkotin	HMDB
Nectadon	HMDB
Nicolane	HMDB
Nipaxon	HMDB
Noscapal	HMDB
Noscapalin	HMDB
Noscapin	HMDB
Noscapine (JP15/usp/inn)	HMDB
Noscopine	HMDB
O-Methylnarcotoline	HMDB
Opian	HMDB
Opianin	HMDB
Opianine	HMDB
Terbenol	HMDB
Tusscapine	HMDB
Vadebex	HMDB
Hydrogen embonate, noscapine	MeSH
Noscapine hydrogen embonate	MeSH
Hydrochloride, noscapine	MeSH
Prikkelhoest, librochin	MeSH
Noscapine hydrochloride	MeSH
Librochin prikkelhoest	MeSH
Embonate, noscapine hydrogen	MeSH
Narcotine	MeSH
Tuscalman	MeSH
Capval tropfen	MeSH
Tropfen, capval	MeSH
Noscapect	MeSH
(-)-alpha-Narcotine	ChEBI

Chemical Formula

C₂₂H₂₃NO₇

Average Mass

413.4205 Da

Monoisotopic Mass

413.14745 Da

IUPAC Name

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

Traditional Name

noscapine

CAS Registry Number

Not Available

SMILES

[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12

InChI Identifier

InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

InChI Key

AKNNEGZIBPJZJG-MSOLQXFVSA-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
Apis cerana	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	Plant	KNApSAcK
Corydalis heterocarpa	LOTUS Database	35616633
Corydalis solida	LOTUS Database	35616633
Papaver commutatum	Plant	KNApSAcK
Papaver pseudo-orientale	LOTUS Database	35616633
Papaver rhoeas	Plant	KNApSAcK
Papaver rhopalothece	Plant	KNApSAcK
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
Isobenzofuranone
Benzofuranone
Tetrahydroisoquinoline
Phthalide
Benzodioxole
Isocoumaran
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
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

tertiary amino compound (CHEBI:73237 )
benzylisoquinoline alkaloid (CHEBI:73237 )
cyclic acetal (CHEBI:73237 )
isobenzofuranone (CHEBI:73237 )
Isoquinoline alkaloids (C09592 )

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	ALOGPS
logP	2.58	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	6.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	75.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.08 m³·mol⁻¹	ChemAxon
Polarizability	42.19 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

HMDB0033439

DrugBank ID

DB06174

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Noscapine

METLIN ID

Not Available

PubChem Compound

275196

PDB ID

Not Available

ChEBI ID

73237

Good Scents ID

Not Available

References

General References

Navaee A, Salimi A, Teymourian H: Graphene nanosheets modified glassy carbon electrode for simultaneous detection of heroine, morphine and noscapine. Biosens Bioelectron. 2012 Jan 15;31(1):205-11. doi: 10.1016/j.bios.2011.10.018. Epub 2011 Oct 19. [PubMed:22079300 ]
Yang ZR, Liu M, Peng XL, Lei XF, Zhang JX, Dong WG: Noscapine induces mitochondria-mediated apoptosis in human colon cancer cells in vivo and in vitro. Biochem Biophys Res Commun. 2012 May 11;421(3):627-33. doi: 10.1016/j.bbrc.2012.04.079. Epub 2012 Apr 22. [PubMed:22546556 ]
Winzer T, Gazda V, He Z, Kaminski F, Kern M, Larson TR, Li Y, Meade F, Teodor R, Vaistij FE, Walker C, Bowser TA, Graham IA: A Papaver somniferum 10-gene cluster for synthesis of the anticancer alkaloid noscapine. Science. 2012 Jun 29;336(6089):1704-8. doi: 10.1126/science.1220757. Epub 2012 May 31. [PubMed:22653730 ]
Fang ZZ, Krausz KW, Li F, Cheng J, Tanaka N, Gonzalez FJ: Metabolic map and bioactivation of the anti-tumour drug noscapine. Br J Pharmacol. 2012 Nov;167(6):1271-86. doi: 10.1111/j.1476-5381.2012.02067.x. [PubMed:22671862 ]
Gajewski MM, Alisaraie L, Tuszynski JA: Peloruside, laulimalide, and noscapine interactions with beta-tubulin. Pharm Res. 2012 Nov;29(11):2985-93. doi: 10.1007/s11095-012-0809-2. Epub 2012 Jun 26. [PubMed:22733149 ]

Showing NP-Card for alpha-Narcotine (NP0051006)

MOL for NP0051006 (alpha-Narcotine)

3D MOL for NP0051006 (alpha-Narcotine)

3D SDF for NP0051006 (alpha-Narcotine)

3D-SDF for NP0051006 (alpha-Narcotine)

PDB for NP0051006 (alpha-Narcotine)

3D PDB for NP0051006 (alpha-Narcotine)

SMILES for NP0051006 (alpha-Narcotine)

INCHI for NP0051006 (alpha-Narcotine)

Structure for NP0051006 (alpha-Narcotine)

3D Structure for NP0051006 (alpha-Narcotine)