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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 07:14:09 UTC

Update Date

2021-10-13 04:42:32 UTC

HMDB ID

HMDB0003920

Secondary Accession Numbers

HMDB03920

Metabolite Identification

Common Name

Protopine

Description

Protopine, also known as corydinine or fumarine, belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. Protopine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make protopine a potential biomarker for the consumption of these foods. Protopine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Protopine.

Structure

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


  Mrv0541 02231219482D          

 26 30  0  0  0  0            999 V2000
   24.7401   -7.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4541   -6.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0225   -6.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7330   -7.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4541   -5.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2383   -7.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3085   -7.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0295   -5.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0120   -8.3980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7541   -5.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2349   -5.6721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7167   -6.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3121   -7.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0014   -9.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0355   -8.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6016   -8.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4223   -7.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2804   -9.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6051   -9.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8982   -7.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8911   -9.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1806   -8.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1772   -9.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3858   -8.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3787   -9.4707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9039   -8.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 18 19  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0003920
     RDKit          3D
Protopine
 45 49  0  0  0  0  0  0  0  0999 V2000
   -1.1735    3.1751   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    1.8045   -0.2294 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278    1.7081    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    1.8876    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211    0.7109    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    1.0332    0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182    0.0803    0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -1.2402    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -1.5483    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -0.5832   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -1.1086   -0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -2.1532    0.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -0.6003   -1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6392   -0.9180   -1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1693   -2.1593   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -2.5843   -1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -1.7880   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750   -0.5577    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -0.1247   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    1.2223    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8048    0.0254    0.7893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6452   -1.0151    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485   -1.9278    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305   -1.9657    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -1.0763    0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9572    0.1413    1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    3.2570   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    3.7866   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    3.5913    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    2.4645    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0883    0.7163    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    2.1222   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    2.8197    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    2.0721    0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822   -2.6163    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.3985   -1.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0598   -1.2548   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -2.8158   -1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8021   -3.5525   -1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    1.1304    1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.9096    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -1.4537    2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6736   -0.7009    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3546   -1.3758    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8154   -0.9364   -0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8 24  1  0
 24 25  1  0
 25 26  1  0
 20  2  1  0
 10  5  1  0
 19 14  1  0
 26  7  1  0
 23 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  6 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
M  END


  Mrv0541 02231219482D          

 26 30  0  0  0  0            999 V2000
   24.7401   -7.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4541   -6.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0225   -6.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7330   -7.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4541   -5.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2383   -7.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3085   -7.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0295   -5.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0120   -8.3980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7541   -5.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2349   -5.6721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7167   -6.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3121   -7.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0014   -9.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0355   -8.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6016   -8.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4223   -7.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2804   -9.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6051   -9.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8982   -7.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8911   -9.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1806   -8.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1772   -9.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3858   -8.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3787   -9.4707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9039   -8.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 18 19  1  0  0  0  0
 22 23  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003920

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3

> <INCHI_KEY>
GPTFURBXHJWNHR-UHFFFAOYSA-N

> <FORMULA>
C20H19NO5

> <MOLECULAR_WEIGHT>
353.3686

> <EXACT_MASS>
353.126322723

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.68135899240185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0⁴,¹².0⁶,¹⁰.0¹⁸,²²]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.592985362999999

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.816585504267696

> <JCHEM_PKA_STRONGEST_BASIC>
4.947302519910738

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
94.56880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
protopine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003920
     RDKit          3D
Protopine
 45 49  0  0  0  0  0  0  0  0999 V2000
   -1.1735    3.1751   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    1.8045   -0.2294 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278    1.7081    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    1.8876    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211    0.7109    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    1.0332    0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182    0.0803    0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -1.2402    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -1.5483    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -0.5832   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -1.1086   -0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -2.1532    0.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -0.6003   -1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6392   -0.9180   -1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1693   -2.1593   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -2.5843   -1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -1.7880   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750   -0.5577    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -0.1247   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    1.2223    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8048    0.0254    0.7893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6452   -1.0151    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485   -1.9278    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305   -1.9657    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -1.0763    0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9572    0.1413    1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    3.2570   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    3.7866   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    3.5913    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    2.4645    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0883    0.7163    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    2.1222   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    2.8197    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    2.0721    0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822   -2.6163    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.3985   -1.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0598   -1.2548   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -2.8158   -1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8021   -3.5525   -1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    1.1304    1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.9096    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -1.4537    2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6736   -0.7009    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3546   -1.3758    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8154   -0.9364   -0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8 24  1  0
 24 25  1  0
 25 26  1  0
 20  2  1  0
 10  5  1  0
 19 14  1  0
 26  7  1  0
 23 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  6 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      46.182 -13.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      47.514 -12.610   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      44.842 -12.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      46.168 -14.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.514 -11.067   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      48.978 -13.083   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      43.509 -13.365   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      44.855 -11.061   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      44.822 -15.676   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      46.208 -10.306   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      48.972 -10.588   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      49.871 -11.848   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.516 -14.915   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      44.803 -17.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      46.733 -16.799   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.190 -15.683   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      41.855 -13.949   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      43.457 -17.967   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      42.196 -17.232   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      40.877 -14.915   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.863 -18.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.537 -15.683   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.531 -17.226   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      38.053 -15.203   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      38.040 -17.679   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      37.154 -16.451   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    3   10                                                       
CONECT    9    4   14   15                                                  
CONECT   10    5    8                                                       
CONECT   11    5   12                                                       
CONECT   12    6   11                                                       
CONECT   13    7   16   17                                                  
CONECT   14    9   18                                                       
CONECT   15    9                                                            
CONECT   16   13   19   20                                                  
CONECT   17   13                                                            
CONECT   18   14   19                                                       
CONECT   19   16   21   18                                                  
CONECT   20   16   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24   23                                                  
CONECT   23   21   25   22                                                  
CONECT   24   22   26                                                       
CONECT   25   23   26                                                       
CONECT   26   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

COMPND    HMDB0003920
HETATM    1  C1  UNL     1      -1.173   3.175  -0.589  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.947   1.804  -0.229  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.128   1.708   0.739  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.413   1.888   0.005  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.321   0.711   0.133  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.629   1.033   0.490  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.618   0.080   0.673  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.268  -1.240   0.488  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.972  -1.548   0.136  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.969  -0.583  -0.051  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.672  -1.109  -0.425  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.259  -2.153   0.198  1.00  0.00           O  
HETATM   13  C11 UNL     1      -0.260  -0.600  -1.443  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.639  -0.918  -1.014  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.169  -2.159  -1.398  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.419  -2.584  -1.076  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.235  -1.788  -0.340  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.775  -0.558   0.068  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.471  -0.125  -0.273  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.143   1.222   0.250  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.805   0.025   0.789  1.00  0.00           O  
HETATM   22  C19 UNL     1      -5.645  -1.015   1.244  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.548  -1.928   0.148  1.00  0.00           O  
HETATM   24  O4  UNL     1       5.431  -1.966   0.732  1.00  0.00           O  
HETATM   25  C20 UNL     1       6.532  -1.076   0.586  1.00  0.00           C  
HETATM   26  O5  UNL     1       5.957   0.141   1.019  1.00  0.00           O  
HETATM   27  H1  UNL     1      -1.574   3.257  -1.612  1.00  0.00           H  
HETATM   28  H2  UNL     1      -0.249   3.787  -0.509  1.00  0.00           H  
HETATM   29  H3  UNL     1      -1.905   3.591   0.161  1.00  0.00           H  
HETATM   30  H4  UNL     1      -0.049   2.464   1.542  1.00  0.00           H  
HETATM   31  H5  UNL     1       0.088   0.716   1.277  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.331   2.122  -1.069  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.885   2.820   0.442  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.940   2.072   0.645  1.00  0.00           H  
HETATM   35  H9  UNL     1       2.782  -2.616   0.018  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.089   0.398  -1.822  1.00  0.00           H  
HETATM   37  H11 UNL     1      -0.060  -1.255  -2.367  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.545  -2.816  -1.983  1.00  0.00           H  
HETATM   39  H13 UNL     1      -3.802  -3.553  -1.388  1.00  0.00           H  
HETATM   40  H14 UNL     1      -2.035   1.130   1.369  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.002   1.910   0.085  1.00  0.00           H  
HETATM   42  H16 UNL     1      -5.151  -1.454   2.148  1.00  0.00           H  
HETATM   43  H17 UNL     1      -6.674  -0.701   1.444  1.00  0.00           H  
HETATM   44  H18 UNL     1       7.355  -1.376   1.235  1.00  0.00           H  
HETATM   45  H19 UNL     1       6.815  -0.936  -0.475  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   20
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6    6   10
CONECT    6    7   34
CONECT    7    8    8   26
CONECT    8    9   24
CONECT    9   10   10   35
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   36   37
CONECT   14   15   15   19
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   23
CONECT   18   19   19   21
CONECT   19   20
CONECT   20   40   41
CONECT   21   22
CONECT   22   23   42   43
CONECT   24   25
CONECT   25   26   44   45
END

HMDB0003920
     RDKit          3D
Protopine
 45 49  0  0  0  0  0  0  0  0999 V2000
   -1.1735    3.1751   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    1.8045   -0.2294 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278    1.7081    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    1.8876    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211    0.7109    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    1.0332    0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182    0.0803    0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -1.2402    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -1.5483    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -0.5832   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -1.1086   -0.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -2.1532    0.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -0.6003   -1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6392   -0.9180   -1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1693   -2.1593   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -2.5843   -1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -1.7880   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750   -0.5577    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -0.1247   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    1.2223    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8048    0.0254    0.7893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6452   -1.0151    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485   -1.9278    0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4305   -1.9657    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -1.0763    0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9572    0.1413    1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744    3.2570   -1.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    3.7866   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    3.5913    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    2.4645    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0883    0.7163    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    2.1222   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    2.8197    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    2.0721    0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822   -2.6163    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.3985   -1.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0598   -1.2548   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -2.8158   -1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8021   -3.5525   -1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    1.1304    1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    1.9096    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -1.4537    2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6736   -0.7009    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3546   -1.3758    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8154   -0.9364   -0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8 24  1  0
 24 25  1  0
 25 26  1  0
 20  2  1  0
 10  5  1  0
 19 14  1  0
 26  7  1  0
 23 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  6 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 20 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one	ChEBI
7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one	ChEBI
Corydinine	ChEBI
Fumarine	ChEBI
Macleyine	ChEBI
Biflorine	HMDB
Hypercorine	HMDB
Protopin	HMDB
Protopine mesylate	MeSH, HMDB
Protopine hydrochloride	MeSH, HMDB

Chemical Formula

C₂₀H₁₉NO₅

Average Molecular Weight

353.3686

Monoisotopic Molecular Weight

353.126322723

IUPAC Name

15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0⁴,¹².0⁶,¹⁰.0¹⁸,²²]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one

Traditional Name

protopine

CAS Registry Number

130-86-9

SMILES

CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2

InChI Identifier

InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3

InChI Key

GPTFURBXHJWNHR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protopine alkaloids

Sub Class

Not Available

Direct Parent

Protopine alkaloids

Alternative Parents

Substituents

Protopine skeleton
Benzodioxole
Aryl ketone
Aryl alkyl ketone
Aralkylamine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzazecine alkaloid (CHEBI:16415 )
Isoquinoline alkaloids (C05189 )
a small molecule (PROTOPINE )

Ontology

Disposition

Biological location

Organ

Kidney

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	208 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.82 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	10^(1.95) g/L	ALOGPS
logP	10^(2.59) g/L	ChemAxon
logS	10^(-3.2) g/L	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.57 m³·mol⁻¹	ChemAxon
Polarizability	36.68 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]+	183.341	31661259
DarkChem	[M-H]-	182.091	31661259

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protopine	CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2	4343.4	Standard polar	33892256
Protopine	CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2	2758.5	Standard non polar	33892256
Protopine	CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2	3013.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Protopine GC-MS (1 TMS)	splash10-004r-2931000000-d14db9f8fbba357a7cea	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Protopine GC-MS (Non-derivatized)	splash10-004r-2931000000-d14db9f8fbba357a7cea	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protopine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ri-2049000000-c70fb92c70c89eb31559	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protopine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protopine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-2910000000-c237219498d206631a06	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOF	splash10-0f79-0936000000-da2afff6dba215da666a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOF	splash10-000i-0931000000-3ae8ba25a400b3cfc336	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOF	splash10-0udi-0009000000-d474e4da85bfe6b8622e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOF	splash10-0udi-0009000000-c77daec49f175e0080d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOF	splash10-0udi-0629000000-f410a01812829c61b1b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOF	splash10-000i-0921000000-cb2a7100722bf81f462f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QQ , positive-QTOF	splash10-000i-0930000000-e740d177ef096526ca53	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-IT , positive-QTOF	splash10-000j-0932000000-899dc6a90055430abee2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-1833ae0a6ab82f156d51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QTOF , positive-QTOF	splash10-0udr-0938000000-8a5ae3db2af3946a0e75	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine LC-ESI-QTOF , positive-QTOF	splash10-000i-0920000000-925c965ff2b76b30d02f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine , positive-QTOF	splash10-0f79-0944000000-e1624142a49564f32b99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine 6V, Positive-QTOF	splash10-000i-0910000000-79485782e2b17a1fccef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine 6V, Positive-QTOF	splash10-000i-0931000000-a9d401bee935049397de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine 6V, Positive-QTOF	splash10-000i-0920000000-092e042fc79ca310c193	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine 6V, Positive-QTOF	splash10-000i-0941000000-1fdf197d94d08c882c08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine 10V, Positive-QTOF	splash10-0udi-0009000000-aab71a61504570b7beeb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine 20V, Positive-QTOF	splash10-0udr-0928000000-60509c382ac86776f91c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protopine 40V, Positive-QTOF	splash10-000i-0920000000-925c965ff2b76b30d02f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protopine 10V, Positive-QTOF	splash10-0udi-0009000000-0089e0012db766e23529	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protopine 20V, Positive-QTOF	splash10-0udj-0509000000-ed54f57036aee6ac913c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protopine 40V, Positive-QTOF	splash10-004j-1900000000-e130dfa9e240571ed4e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protopine 10V, Negative-QTOF	splash10-0udi-0009000000-400e98b52794a7bf4fbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protopine 20V, Negative-QTOF	splash10-0udi-0009000000-71833c50697c0a4e532c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protopine 40V, Negative-QTOF	splash10-002f-9658000000-c8824149cc8b247dcb6f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Kidney

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Protopine

METLIN ID

6988

PubChem Compound

4970

PDB ID

Not Available

ChEBI ID

16415

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1836891

References

Synthesis Reference

Rueffer, M.; Zenk, M. H. Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans. Tetrahedron Letters (1987), 28(44), 5307-10.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Paul LD, Maurer HH: Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 5;789(1):43-57. [PubMed:12726842 ]
Wynne PM, Vine JH, Amiet RG: Protopine alkaloids in horse urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Nov 5;811(1):85-91. [PubMed:15458726 ]
Jiang B, Cao K, Wang R: Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells. Eur J Pharmacol. 2004 Dec 15;506(2):93-100. [PubMed:15588728 ]

Showing metabocard for Protopine (HMDB0003920)

MOL for HMDB0003920 (Protopine)

3D MOL for HMDB0003920 (Protopine)

3D SDF for HMDB0003920 (Protopine)

3D-SDF for HMDB0003920 (Protopine)

PDB for HMDB0003920 (Protopine)

3D PDB for HMDB0003920 (Protopine)

SMILES for HMDB0003920 (Protopine)

INCHI for HMDB0003920 (Protopine)

Structure for HMDB0003920 (Protopine)

3D Structure for HMDB0003920 (Protopine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra