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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:10:24 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033439

Secondary Accession Numbers

HMDB33439

Metabolite Identification

Common Name

(-)-alpha-Narcotine

Description

(-)-alpha-Narcotine is found in opium poppy. (-)-alpha-Narcotine is an alkaloid from Papaver somniferum (opium poppy).Noscapine (also known as Narcotine, Nectodon, Nospen, and Anarcotine) is a benzylisoquinoline alkaloid from plants of the Papaveraceae family, without significant painkilling properties. This agent is primarily used for its antitussive (cough-suppressing) effects. It has also been shown to have anticancer activity. (Wikipedia ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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
  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

HMDB0033439
     RDKit          3D
(-)-alpha-Narcotine
 53 57  0  0  0  0  0  0  0  0999 V2000
    6.4465    1.0985    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    0.1492   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    0.0228    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224    0.7952    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920    0.6639    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -0.2586    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429   -1.0114   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -0.9015   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -1.6951   -1.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2605   -1.2936   -3.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -1.8830   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -2.7182   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -1.6187   -0.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055   -0.6618    0.6227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7277    0.5179    0.4771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1346    0.0712    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6923   -0.2310    1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0023   -0.6537    1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7464   -0.7763    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2192   -0.4820   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859   -0.0517   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450    0.2477   -1.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6879   -0.5721   -2.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579   -0.6814   -1.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4154   -0.8318   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0647   -1.1748    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.0814    2.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    0.9679    2.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    1.4636    1.5339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589    2.6920    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1645    2.1158    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594    1.0179    1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5364    0.9403    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834    1.5241    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    1.2583    2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775   -0.5711   -3.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975   -2.2170   -3.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2724   -0.9299   -3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -1.1742    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5052    1.0248   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4312   -0.8912    2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0768   -0.3348   -3.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -0.4084   -2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -1.6505   -2.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0088   -1.6301   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9743    0.1230   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    0.2676    3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -1.0629    3.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.8794    3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    0.5628    3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422    2.9371    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    3.5328    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    2.5743    1.2961 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  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  8  3  1  0
 29 15  1  0
 14  6  1  0
 21 16  2  0
 26 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 14 39  1  1
 15 40  1  6
 18 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 25 45  1  0
 25 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 30 51  1  0
 30 52  1  0
 30 53  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
    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
  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>
HMDB0033439

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0033439
     RDKit          3D
(-)-alpha-Narcotine
 53 57  0  0  0  0  0  0  0  0999 V2000
    6.4465    1.0985    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    0.1492   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    0.0228    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224    0.7952    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920    0.6639    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -0.2586    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429   -1.0114   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -0.9015   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -1.6951   -1.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2605   -1.2936   -3.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -1.8830   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -2.7182   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -1.6187   -0.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055   -0.6618    0.6227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7277    0.5179    0.4771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1346    0.0712    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6923   -0.2310    1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0023   -0.6537    1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7464   -0.7763    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2192   -0.4820   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859   -0.0517   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450    0.2477   -1.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6879   -0.5721   -2.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579   -0.6814   -1.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4154   -0.8318   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0647   -1.1748    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.0814    2.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    0.9679    2.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    1.4636    1.5339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589    2.6920    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1645    2.1158    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594    1.0179    1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5364    0.9403    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834    1.5241    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    1.2583    2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775   -0.5711   -3.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975   -2.2170   -3.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2724   -0.9299   -3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -1.1742    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5052    1.0248   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4312   -0.8912    2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0768   -0.3348   -3.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -0.4084   -2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -1.6505   -2.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0088   -1.6301   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9743    0.1230   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    0.2676    3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -1.0629    3.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.8794    3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    0.5628    3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422    2.9371    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    3.5328    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    2.5743    1.2961 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  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  8  3  1  0
 29 15  1  0
 14  6  1  0
 21 16  2  0
 26 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 14 39  1  1
 15 40  1  6
 18 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 25 45  1  0
 25 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 30 51  1  0
 30 52  1  0
 30 53  1  0
M  END

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

COMPND    HMDB0033439
HETATM    1  C1  UNL     1       6.446   1.098   0.455  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.691   0.149  -0.274  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.340   0.023   0.017  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.722   0.795   0.992  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.392   0.664   1.272  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.621  -0.259   0.576  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.243  -1.011  -0.382  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.607  -0.901  -0.693  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.196  -1.695  -1.682  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.261  -1.294  -3.032  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.239  -1.883  -0.979  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.489  -2.718  -1.909  1.00  0.00           O  
HETATM   13  O4  UNL     1       0.054  -1.619  -0.358  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.206  -0.662   0.623  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.728   0.518   0.477  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.135   0.071   0.457  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.692  -0.231   1.682  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.002  -0.654   1.700  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.746  -0.776   0.549  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.219  -0.482  -0.684  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.886  -0.052  -0.706  1.00  0.00           C  
HETATM   22  O5  UNL     1      -2.345   0.248  -1.923  1.00  0.00           O  
HETATM   23  C18 UNL     1      -1.688  -0.572  -2.818  1.00  0.00           C  
HETATM   24  O6  UNL     1      -5.158  -0.681  -1.691  1.00  0.00           O  
HETATM   25  C19 UNL     1      -6.415  -0.832  -1.033  1.00  0.00           C  
HETATM   26  O7  UNL     1      -6.065  -1.175   0.300  1.00  0.00           O  
HETATM   27  C20 UNL     1      -1.903  -0.081   2.952  1.00  0.00           C  
HETATM   28  C21 UNL     1      -0.859   0.968   2.846  1.00  0.00           C  
HETATM   29  N1  UNL     1      -0.564   1.464   1.534  1.00  0.00           N  
HETATM   30  C22 UNL     1      -1.259   2.692   1.221  1.00  0.00           C  
HETATM   31  H1  UNL     1       6.164   2.116   0.056  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.259   1.018   1.544  1.00  0.00           H  
HETATM   33  H3  UNL     1       7.536   0.940   0.319  1.00  0.00           H  
HETATM   34  H4  UNL     1       4.283   1.524   1.557  1.00  0.00           H  
HETATM   35  H5  UNL     1       1.940   1.258   2.012  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.078  -0.571  -3.230  1.00  0.00           H  
HETATM   37  H7  UNL     1       4.497  -2.217  -3.625  1.00  0.00           H  
HETATM   38  H8  UNL     1       3.272  -0.930  -3.409  1.00  0.00           H  
HETATM   39  H9  UNL     1       0.064  -1.174   1.604  1.00  0.00           H  
HETATM   40  H10 UNL     1      -0.505   1.025  -0.475  1.00  0.00           H  
HETATM   41  H11 UNL     1      -4.431  -0.891   2.687  1.00  0.00           H  
HETATM   42  H12 UNL     1      -2.077  -0.335  -3.849  1.00  0.00           H  
HETATM   43  H13 UNL     1      -0.590  -0.408  -2.760  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.857  -1.650  -2.678  1.00  0.00           H  
HETATM   45  H15 UNL     1      -7.009  -1.630  -1.525  1.00  0.00           H  
HETATM   46  H16 UNL     1      -6.974   0.123  -1.005  1.00  0.00           H  
HETATM   47  H17 UNL     1      -2.636   0.268   3.743  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.562  -1.063   3.331  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.089   1.879   3.475  1.00  0.00           H  
HETATM   50  H20 UNL     1       0.073   0.563   3.288  1.00  0.00           H  
HETATM   51  H21 UNL     1      -1.042   2.937   0.160  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.874   3.533   1.828  1.00  0.00           H  
HETATM   53  H23 UNL     1      -2.363   2.574   1.296  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   34
CONECT    5    6    6   35
CONECT    6    7   14
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   36   37   38
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   39
CONECT   15   16   29   40
CONECT   16   17   21   21
CONECT   17   18   18   27
CONECT   18   19   41
CONECT   19   20   20   26
CONECT   20   21   24
CONECT   21   22
CONECT   22   23
CONECT   23   42   43   44
CONECT   24   25
CONECT   25   26   45   46
CONECT   27   28   47   48
CONECT   28   29   49   50
CONECT   29   30
CONECT   30   51   52   53
END

HMDB0033439
     RDKit          3D
(-)-alpha-Narcotine
 53 57  0  0  0  0  0  0  0  0999 V2000
    6.4465    1.0985    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    0.1492   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    0.0228    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224    0.7952    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3920    0.6639    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -0.2586    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429   -1.0114   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -0.9015   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -1.6951   -1.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2605   -1.2936   -3.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -1.8830   -0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -2.7182   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -1.6187   -0.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055   -0.6618    0.6227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7277    0.5179    0.4771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1346    0.0712    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6923   -0.2310    1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0023   -0.6537    1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7464   -0.7763    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2192   -0.4820   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859   -0.0517   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450    0.2477   -1.9227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6879   -0.5721   -2.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579   -0.6814   -1.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4154   -0.8318   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0647   -1.1748    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.0814    2.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    0.9679    2.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    1.4636    1.5339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589    2.6920    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1645    2.1158    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594    1.0179    1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5364    0.9403    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834    1.5241    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396    1.2583    2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775   -0.5711   -3.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975   -2.2170   -3.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2724   -0.9299   -3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -1.1742    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5052    1.0248   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4312   -0.8912    2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0768   -0.3348   -3.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -0.4084   -2.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -1.6505   -2.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0088   -1.6301   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9743    0.1230   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    0.2676    3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -1.0629    3.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.8794    3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    0.5628    3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422    2.9371    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    3.5328    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    2.5743    1.2961 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  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  8  3  1  0
 29 15  1  0
 14  6  1  0
 21 16  2  0
 26 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 14 39  1  1
 15 40  1  6
 18 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 25 45  1  0
 25 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 30 51  1  0
 30 52  1  0
 30 53  1  0
M  END

View in JSmol View Stereo Labels

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	MeSH
Capval tropfen	MeSH
Embonate, noscapine hydrogen	MeSH
Hydrochloride, noscapine	MeSH
Hydrogen embonate, noscapine	MeSH
Librochin prikkelhoest	MeSH
Narcotine	MeSH
Noscapect	MeSH
Noscapine hydrochloride	MeSH
Noscapine hydrogen embonate	MeSH
Tropfen, capval	MeSH
Tuscalman	MeSH
Prikkelhoest, librochin	MeSH
(-)-alpha-Narcotine	ChEBI
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

Chemical Formula

C₂₂H₂₃NO₇

Average Molecular Weight

413.4205

Monoisotopic Molecular Weight

413.147452095

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

128-62-1

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

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 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033439)
Cytoplasm (HMDB: HMDB0033439)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033439)

Source

Exogenous

Exogenous (HMDB: HMDB0033439)

Food

Food (HMDB: HMDB0033439)

Herb and spice

Spice

Opium poppy (FooDB: FOOD00438)

Endogenous

Plant

Plant (HMDB: HMDB0033439)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0033439)

Biological role

Nutrient (HMDB: HMDB0033439)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.3 mg/mL at 30 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.602	31661259
DarkChem	[M-H]-	191.392	31661259
DeepCCS	[M-2H]-	216.443	30932474
DeepCCS	[M+Na]+	191.869	30932474
AllCCS	[M+H]+	197.6	32859911
AllCCS	[M+H-H2O]+	194.9	32859911
AllCCS	[M+NH4]+	200.0	32859911
AllCCS	[M+Na]+	200.7	32859911
AllCCS	[M-H]-	202.5	32859911
AllCCS	[M+Na-2H]-	202.5	32859911
AllCCS	[M+HCOO]-	202.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.25 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7421 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1709.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	192.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	389.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	515.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	456.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	833.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	343.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1343.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	296.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	271.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-alpha-Narcotine	[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12	4578.9	Standard polar	33892256
(-)-alpha-Narcotine	[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12	3142.6	Standard non polar	33892256
(-)-alpha-Narcotine	[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12	3128.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06174

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1142581

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (-)-alpha-Narcotine (HMDB0033439)

MOL for HMDB0033439 ((-)-alpha-Narcotine)

3D MOL for HMDB0033439 ((-)-alpha-Narcotine)

3D SDF for HMDB0033439 ((-)-alpha-Narcotine)

3D-SDF for HMDB0033439 ((-)-alpha-Narcotine)

PDB for HMDB0033439 ((-)-alpha-Narcotine)

3D PDB for HMDB0033439 ((-)-alpha-Narcotine)

SMILES for HMDB0033439 ((-)-alpha-Narcotine)

INCHI for HMDB0033439 ((-)-alpha-Narcotine)

Structure for HMDB0033439 ((-)-alpha-Narcotine)

3D Structure for HMDB0033439 ((-)-alpha-Narcotine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized