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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:10:32 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033441

Secondary Accession Numbers

HMDB33441

Metabolite Identification

Common Name

(±)-alpha-Narcotine

Description

(±)-alpha-Narcotine 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. Based on a literature review very few articles have been published on (±)-alpha-Narcotine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061307072D          

 30 34  0  0  0  0            999 V2000
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8531    6.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871    6.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2589    3.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110    4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560    4.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7491    5.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871    5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081    5.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941    5.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171    3.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  1  0  0  0  0
 23  1  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
 24 22  2  0  0  0  0
 25  2  1  0  0  0  0
 25 13  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
 27  4  1  0  0  0  0
 27 21  1  0  0  0  0
 28 10  1  0  0  0  0
 28 14  1  0  0  0  0
 29 10  1  0  0  0  0
 29 20  1  0  0  0  0
 30 18  1  0  0  0  0
 30 22  1  0  0  0  0
M  END

HMDB0033441
     RDKit          3D
(±)-alpha-Narcotine
 53 57  0  0  0  0  0  0  0  0999 V2000
    6.2093   -1.8936   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6767   -0.6518   -0.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3317   -0.4989   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834   -1.5820   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1414   -1.4088   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426   -0.1878    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    0.8850    0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185    0.7183    0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791    1.8006    0.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3988    2.1585    1.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.9906    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397    3.1533    1.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    1.5178    0.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    0.1803    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252   -0.2773   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -0.4160   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8344   -1.2440   -0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1544   -1.5289   -0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8378   -0.9736    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -0.1612    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    0.1203    1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    0.9617    2.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.3885    1.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1598    0.2248    2.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3005   -0.6292    1.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1898   -1.0990    0.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816   -1.7844   -2.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614   -0.7454   -2.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110    0.2489   -1.6420 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769    1.4770   -1.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2522   -1.7896   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573   -2.5798   -0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5467   -2.3142   -1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8571   -2.5421   -0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4905   -2.2643   -0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3152    1.5230    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6600    3.2384    1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968    2.0649    2.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951   -0.4076    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -1.3974   -0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6504   -2.1747   -1.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3949    2.6796    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248    2.9290    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463    2.6570    0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2118   -0.0356    2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2485   -1.4894    2.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -2.1112   -2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -2.6707   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -0.2518   -3.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243   -1.2294   -2.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759    1.4949   -2.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368    2.3683   -1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383    1.5591   -1.3281 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  0
 15 40  1  0
 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 05061307072D          

 30 34  0  0  0  0            999 V2000
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8531    6.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871    6.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2589    3.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110    4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5560    4.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7491    5.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871    5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081    5.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941    5.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171    3.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  1  0  0  0  0
 23  1  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
 24 22  2  0  0  0  0
 25  2  1  0  0  0  0
 25 13  1  0  0  0  0
 26  3  1  0  0  0  0
 26 19  1  0  0  0  0
 27  4  1  0  0  0  0
 27 21  1  0  0  0  0
 28 10  1  0  0  0  0
 28 14  1  0  0  0  0
 29 10  1  0  0  0  0
 29 20  1  0  0  0  0
 30 18  1  0  0  0  0
 30 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033441

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(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

> <INCHI_KEY>
AKNNEGZIBPJZJG-UHFFFAOYSA-N

> <FORMULA>
C22H23NO7

> <MOLECULAR_WEIGHT>
413.4205

> <EXACT_MASS>
413.147452095

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
42.33881977058084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dimethoxy-3-{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>
6.444144933804222

> <JCHEM_POLAR_SURFACE_AREA>
75.69000000000001

> <JCHEM_REFRACTIVITY>
107.07609999999995

> <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

$$$$

HMDB0033441
     RDKit          3D
(±)-alpha-Narcotine
 53 57  0  0  0  0  0  0  0  0999 V2000
    6.2093   -1.8936   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6767   -0.6518   -0.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3317   -0.4989   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834   -1.5820   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1414   -1.4088   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426   -0.1878    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    0.8850    0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185    0.7183    0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791    1.8006    0.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3988    2.1585    1.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.9906    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397    3.1533    1.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    1.5178    0.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    0.1803    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252   -0.2773   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -0.4160   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8344   -1.2440   -0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1544   -1.5289   -0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8378   -0.9736    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -0.1612    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    0.1203    1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    0.9617    2.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.3885    1.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1598    0.2248    2.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3005   -0.6292    1.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1898   -1.0990    0.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816   -1.7844   -2.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614   -0.7454   -2.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110    0.2489   -1.6420 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769    1.4770   -1.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2522   -1.7896   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573   -2.5798   -0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5467   -2.3142   -1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8571   -2.5421   -0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4905   -2.2643   -0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3152    1.5230    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6600    3.2384    1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968    2.0649    2.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951   -0.4076    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -1.3974   -0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6504   -2.1747   -1.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3949    2.6796    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248    2.9290    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463    2.6570    0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2118   -0.0356    2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2485   -1.4894    2.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -2.1112   -2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -2.6707   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -0.2518   -3.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243   -1.2294   -2.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759    1.4949   -2.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368    2.3683   -1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383    1.5591   -1.3281 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  0
 15 40  1  0
 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                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.059  11.726   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.016  11.222   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.950   6.508   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.981   7.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.444   6.828   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.505   9.117   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.968   8.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.998   9.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.428   8.293   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       6.531   3.613   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       3.523   9.538   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.535  10.261   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.522  10.902   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.952   6.828   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7    8   11                                                       
CONECT    8    7   23                                                       
CONECT    9   11   14                                                       
CONECT   10   28   29                                                       
CONECT   11    7    9   15                                                  
CONECT   12    5   16   18                                                  
CONECT   13    6   19   25                                                  
CONECT   14    9   20   28                                                  
CONECT   15   11   17   21                                                  
CONECT   16   12   19   22                                                  
CONECT   17   15   18   23                                                  
CONECT   18   12   17   30                                                  
CONECT   19   13   16   26                                                  
CONECT   20   14   21   29                                                  
CONECT   21   15   20   27                                                  
CONECT   22   16   24   30                                                  
CONECT   23    1    8   17                                                  
CONECT   24   22                                                            
CONECT   25    2   13                                                       
CONECT   26    3   19                                                       
CONECT   27    4   21                                                       
CONECT   28   10   14                                                       
CONECT   29   10   20                                                       
CONECT   30   18   22                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

COMPND    HMDB0033441
HETATM    1  C1  UNL     1       6.209  -1.894  -1.046  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.677  -0.652  -0.638  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.332  -0.499  -0.324  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.483  -1.582  -0.410  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.141  -1.409  -0.092  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.643  -0.188   0.304  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.472   0.885   0.391  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.819   0.718   0.073  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.679   1.801   0.156  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.399   2.158   1.300  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.650   1.991   0.825  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.040   3.153   1.024  1.00  0.00           O  
HETATM   13  O4  UNL     1       0.365   1.518   0.976  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.228   0.180   0.684  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.725  -0.277  -0.314  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.143  -0.416  -0.013  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.834  -1.244  -0.921  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.154  -1.529  -0.800  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.838  -0.974   0.269  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.201  -0.161   1.175  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.832   0.120   1.027  1.00  0.00           C  
HETATM   22  O5  UNL     1      -2.325   0.962   2.011  1.00  0.00           O  
HETATM   23  C18 UNL     1      -2.449   2.389   1.845  1.00  0.00           C  
HETATM   24  O6  UNL     1      -5.160   0.225   2.112  1.00  0.00           O  
HETATM   25  C19 UNL     1      -6.301  -0.629   1.963  1.00  0.00           C  
HETATM   26  O7  UNL     1      -6.190  -1.099   0.633  1.00  0.00           O  
HETATM   27  C20 UNL     1      -1.982  -1.784  -2.043  1.00  0.00           C  
HETATM   28  C21 UNL     1      -1.061  -0.745  -2.590  1.00  0.00           C  
HETATM   29  N1  UNL     1      -0.611   0.249  -1.642  1.00  0.00           N  
HETATM   30  C22 UNL     1      -1.277   1.477  -1.880  1.00  0.00           C  
HETATM   31  H1  UNL     1       7.252  -1.790  -1.379  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.157  -2.580  -0.160  1.00  0.00           H  
HETATM   33  H3  UNL     1       5.547  -2.314  -1.836  1.00  0.00           H  
HETATM   34  H4  UNL     1       3.857  -2.542  -0.717  1.00  0.00           H  
HETATM   35  H5  UNL     1       1.491  -2.264  -0.163  1.00  0.00           H  
HETATM   36  H6  UNL     1       6.315   1.523   1.351  1.00  0.00           H  
HETATM   37  H7  UNL     1       5.660   3.238   1.206  1.00  0.00           H  
HETATM   38  H8  UNL     1       4.797   2.065   2.228  1.00  0.00           H  
HETATM   39  H9  UNL     1       0.095  -0.408   1.648  1.00  0.00           H  
HETATM   40  H10 UNL     1      -0.389  -1.397  -0.489  1.00  0.00           H  
HETATM   41  H11 UNL     1      -4.650  -2.175  -1.525  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.395   2.680   2.343  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.625   2.929   2.311  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.546   2.657   0.784  1.00  0.00           H  
HETATM   45  H15 UNL     1      -7.212  -0.036   2.047  1.00  0.00           H  
HETATM   46  H16 UNL     1      -6.248  -1.489   2.650  1.00  0.00           H  
HETATM   47  H17 UNL     1      -2.667  -2.111  -2.854  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.403  -2.671  -1.717  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.514  -0.252  -3.499  1.00  0.00           H  
HETATM   50  H20 UNL     1      -0.124  -1.229  -2.996  1.00  0.00           H  
HETATM   51  H21 UNL     1      -1.576   1.495  -2.971  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.637   2.368  -1.746  1.00  0.00           H  
HETATM   53  H23 UNL     1      -2.238   1.559  -1.328  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

HMDB0033441
     RDKit          3D
(±)-alpha-Narcotine
 53 57  0  0  0  0  0  0  0  0999 V2000
    6.2093   -1.8936   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6767   -0.6518   -0.6382 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3317   -0.4989   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834   -1.5820   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1414   -1.4088   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426   -0.1878    0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    0.8850    0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185    0.7183    0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6791    1.8006    0.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3988    2.1585    1.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.9906    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397    3.1533    1.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655    1.5178    0.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    0.1803    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252   -0.2773   -0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -0.4160   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8344   -1.2440   -0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1544   -1.5289   -0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8378   -0.9736    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012   -0.1612    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    0.1203    1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    0.9617    2.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.3885    1.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1598    0.2248    2.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3005   -0.6292    1.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1898   -1.0990    0.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816   -1.7844   -2.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614   -0.7454   -2.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110    0.2489   -1.6420 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769    1.4770   -1.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2522   -1.7896   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573   -2.5798   -0.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5467   -2.3142   -1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8571   -2.5421   -0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4905   -2.2643   -0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3152    1.5230    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6600    3.2384    1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968    2.0649    2.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951   -0.4076    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -1.3974   -0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6504   -2.1747   -1.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3949    2.6796    2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248    2.9290    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463    2.6570    0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2118   -0.0356    2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2485   -1.4894    2.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -2.1112   -2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -2.6707   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -0.2518   -3.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243   -1.2294   -2.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759    1.4949   -2.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368    2.3683   -1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383    1.5591   -1.3281 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  0
 15 40  1  0
 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
(±)-a-narcotine	Generator
(±)-α-narcotine	Generator
(+/-)-noscapine	ChEMBL, HMDB
(+/-) a-narcotine	HMDB
(.+-.)-alpha-narcotine	HMDB
(.+-.)-narcotine	HMDB
a-Gnoscopine	HMDB
alpha-Gnoscopine	HMDB
DL-Narcotine	HMDB
Gnoscopine	HMDB
Berna brand OF noscapine hydrochloride	MeSH, HMDB
dreluso Brand OF noscapine	MeSH, HMDB
Embonate, noscapine hydrogen	MeSH, HMDB
Librochin prikkelhoest	MeSH, HMDB
Noscapine dreluso brand	MeSH, HMDB
Tropfen, capval	MeSH, HMDB
Tuscalman	MeSH, HMDB
Boots brand OF noscapine hydrochloride	MeSH, HMDB
Byk brand OF noscapine hydrochloride	MeSH, HMDB
dreluso Brand OF noscapine hydrochloride	MeSH, HMDB
Noscapect	MeSH, HMDB
Noscapine	MeSH, HMDB
Noscapine hydrogen embonate	MeSH, HMDB
Capval tropfen	MeSH, HMDB
Hydrochloride, noscapine	MeSH, HMDB
Capval	MeSH, HMDB
Hydrogen embonate, noscapine	MeSH, HMDB
Noscapine hydrochloride	MeSH, HMDB
Prikkelhoest, librochin	MeSH, HMDB
Narcotine	MeSH

Chemical Formula

C₂₂H₂₃NO₇

Average Molecular Weight

413.4205

Monoisotopic Molecular Weight

413.147452095

IUPAC Name

6,7-dimethoxy-3-{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

6035-40-1

SMILES

COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(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

InChI Key

AKNNEGZIBPJZJG-UHFFFAOYSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033441)
Cytoplasm (HMDB: HMDB0033441)

Source

Exogenous

Food

Food (HMDB: HMDB0033441)

Not Available

Nutrient (HMDB: HMDB0033441)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	230 - 233 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.044 mg/mL at 20 °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	42.34 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]+	192.203	31661259
DarkChem	[M-H]-	189.517	31661259
DeepCCS	[M-2H]-	223.413	30932474
DeepCCS	[M+Na]+	198.641	30932474
AllCCS	[M+H]+	197.7	32859911
AllCCS	[M+H-H2O]+	195.0	32859911
AllCCS	[M+NH4]+	200.1	32859911
AllCCS	[M+Na]+	200.8	32859911
AllCCS	[M-H]-	202.6	32859911
AllCCS	[M+Na-2H]-	202.6	32859911
AllCCS	[M+HCOO]-	202.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-alpha-Narcotine	COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12	4577.0	Standard polar	33892256
(??)-alpha-Narcotine	COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12	3213.0	Standard non polar	33892256
(??)-alpha-Narcotine	COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12	3097.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-alpha-Narcotine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0090000000-3c9ba32ffef0cb240424	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-alpha-Narcotine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QFT , positive-QTOF	splash10-03di-0010900000-cdd1247660f106a951f8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QFT , positive-QTOF	splash10-00di-0095100000-9600e118d85ae53c098b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QFT , positive-QTOF	splash10-00di-0095000000-da9f07f22cfbc8de1589	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QFT , positive-QTOF	splash10-05fr-0093000000-0bd2017e1bcc5746d029	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QFT , positive-QTOF	splash10-0a4i-0291000000-bbe1cf250f43716443dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QFT , positive-QTOF	splash10-0a4i-0590000000-a8e70dcad06bd7414fcb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QTOF , positive-QTOF	splash10-03di-0000900000-c9769de8c704796705c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QTOF , positive-QTOF	splash10-0229-0095800000-2c1c0615cb0341b18dee	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QTOF , positive-QTOF	splash10-00di-0079000000-a8be17dcb81cbaeb32b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QTOF , positive-QTOF	splash10-05fr-0094000000-bf20e99af379ddfd1eb1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0291000000-7c2db78d383690296165	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine , positive-QTOF	splash10-05fr-0394000000-4ff7d94b3c87b88e259f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine , positive-QTOF	splash10-00di-0193000000-9ebb9c8bd7bea33e777c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine 15V, Positive-QTOF	splash10-03k9-0062900000-d48438307b64d04a2721	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine 20V, Positive-QTOF	splash10-00di-0096200000-0e46351b9e099dd035ff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine 30V, Positive-QTOF	splash10-00di-0079000000-6585d8ae7e5c4f5b7b3f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine 45V, Positive-QTOF	splash10-00di-0091000000-ba865760e33b0b19ece8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine 35V, Positive-QTOF	splash10-00di-0091100000-b342c4c749bcb447d17c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-alpha-Narcotine 40V, Positive-QTOF	splash10-05fr-0094000000-0db4dbd2856ec0f4afed	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-alpha-Narcotine 10V, Positive-QTOF	splash10-03di-0013900000-5b826e3916f6a190b5d4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-alpha-Narcotine 20V, Positive-QTOF	splash10-03k9-0349500000-0a1171b8ad158af511de	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-alpha-Narcotine 40V, Positive-QTOF	splash10-0f96-1938000000-0226d383a4c62f6dd51a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-alpha-Narcotine 10V, Negative-QTOF	splash10-03di-0002900000-3e5155cb1df43a1ee339	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-alpha-Narcotine 20V, Negative-QTOF	splash10-03yj-0009300000-554dd8c085d71b8e8c59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-alpha-Narcotine 40V, Negative-QTOF	splash10-0i6u-1109000000-3b5e0f2ae056ecae25b2	2016-08-03	Wishart Lab	View Spectrum

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011479

KNApSAcK ID

Not Available

Chemspider ID

4385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4544

PDB ID

Not Available

ChEBI ID

110185

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 (HMDB0033441)

MOL for HMDB0033441 ((±)-alpha-Narcotine)

3D MOL for HMDB0033441 ((±)-alpha-Narcotine)

3D SDF for HMDB0033441 ((±)-alpha-Narcotine)

3D-SDF for HMDB0033441 ((±)-alpha-Narcotine)

PDB for HMDB0033441 ((±)-alpha-Narcotine)

3D PDB for HMDB0033441 ((±)-alpha-Narcotine)

SMILES for HMDB0033441 ((±)-alpha-Narcotine)

INCHI for HMDB0033441 ((±)-alpha-Narcotine)

Structure for HMDB0033441 ((±)-alpha-Narcotine)

3D Structure for HMDB0033441 ((±)-alpha-Narcotine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra