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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:00 UTC

Update Date

2022-03-07 02:52:08 UTC

HMDB ID

HMDB0029367

Secondary Accession Numbers

HMDB29367

Metabolite Identification

Common Name

Sanguinarine

Description

Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule.[citation needed]; Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine

Structure

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


  Mrv0541 05061304452D          

 25 30  0  0  0  0            999 V2000
    4.1176   -0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -3.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7760   -3.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378   -3.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187   -3.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9091   -3.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2608   -1.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036   -1.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4094   -1.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0900   -3.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -2.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7659   -2.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3086   -2.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946   -2.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4040   -2.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9468   -2.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -1.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -1.4833    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.2139   -2.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2257   -2.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7013   -1.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148   -1.2714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  4  1  0  0  0  0
 13  3  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  2  0  0  0  0
 15 12  1  0  0  0  0
 16  5  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 18 17  2  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  2  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
 23  9  1  0  0  0  0
 23 17  1  0  0  0  0
 24  9  1  0  0  0  0
 24 18  1  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
M  CHG  1  21   1
M  END

HMDB0029367
     RDKit          3D
Sanguinarine
 39 44  0  0  0  0  0  0  0  0999 V2000
    0.5543    2.2754   -0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    1.1943   -0.4358 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5676    1.3315   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    0.3631    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581    0.6129    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6235   -0.3747    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138   -1.6009    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354   -1.8660    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190   -0.8426    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -1.0327    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201   -2.2469    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -2.5156    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -1.5016    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4954   -1.7581    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762   -0.7842   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.4520   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    0.7403   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714   -0.2311   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2900    0.0064   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9915    1.2477   -0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1696    0.5740   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634   -0.7625   -0.2730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    0.1512    0.4625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8068    1.5592    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4983    1.7584   -0.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0303    2.1258   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    3.0149   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    3.0000   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569    2.3140   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600   -2.4067    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -2.8362    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -3.0488    1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -3.4654    0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8516   -2.7306    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115    1.7013   -0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9628    0.6539   -1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6006    0.9635    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465    2.0625    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5641    1.9023   -0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  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
 16 20  1  0
 20 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  1  0
 24 25  1  0
 19  2  1  0
  9  4  1  0
 19 10  1  0
 25  5  1  0
 18 13  1  0
 22 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  7 30  1  0
  8 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
 21 36  1  0
 21 37  1  0
 24 38  1  0
 24 39  1  0
M  CHG  1   2   1
M  END


  Mrv0541 05061304452D          

 25 30  0  0  0  0            999 V2000
    4.1176   -0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -3.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7760   -3.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378   -3.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187   -3.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9091   -3.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2608   -1.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036   -1.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4094   -1.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264   -1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0900   -3.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -2.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7659   -2.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3086   -2.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946   -2.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4040   -2.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9468   -2.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895   -1.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -1.4833    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.2139   -2.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2257   -2.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7013   -1.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148   -1.2714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  4  1  0  0  0  0
 13  3  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  2  0  0  0  0
 15 12  1  0  0  0  0
 16  5  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 18 17  2  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  2  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
 23  9  1  0  0  0  0
 23 17  1  0  0  0  0
 24  9  1  0  0  0  0
 24 18  1  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
HMDB0029367

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+]1=C2C3=CC4=C(OCO4)C=C3C=CC2=C2C=CC3=C(OCO3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1

> <INCHI_KEY>
INVGWHRKADIJHF-UHFFFAOYSA-N

> <FORMULA>
C20H14NO4

> <MOLECULAR_WEIGHT>
332.3295

> <EXACT_MASS>
332.092282941

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.61841848660366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaen-24-ium

> <ALOGPS_LOGP>
-0.51

> <JCHEM_LOGP>
-0.9434966418050794

> <ALOGPS_LOGS>
-6.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.465535933156468

> <JCHEM_POLAR_SURFACE_AREA>
40.8

> <JCHEM_REFRACTIVITY>
90.8184

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sanguinarine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029367
     RDKit          3D
Sanguinarine
 39 44  0  0  0  0  0  0  0  0999 V2000
    0.5543    2.2754   -0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    1.1943   -0.4358 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5676    1.3315   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    0.3631    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581    0.6129    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6235   -0.3747    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138   -1.6009    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354   -1.8660    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190   -0.8426    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -1.0327    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201   -2.2469    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -2.5156    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -1.5016    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4954   -1.7581    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762   -0.7842   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.4520   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    0.7403   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714   -0.2311   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2900    0.0064   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9915    1.2477   -0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1696    0.5740   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634   -0.7625   -0.2730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    0.1512    0.4625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8068    1.5592    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4983    1.7584   -0.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0303    2.1258   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    3.0149   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    3.0000   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569    2.3140   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600   -2.4067    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -2.8362    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -3.0488    1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -3.4654    0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8516   -2.7306    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115    1.7013   -0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9628    0.6539   -1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6006    0.9635    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465    2.0625    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5641    1.9023   -0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  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
 16 20  1  0
 20 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  1  0
 24 25  1  0
 19  2  1  0
  9  4  1  0
 19 10  1  0
 25  5  1  0
 18 13  1  0
 22 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  7 30  1  0
  8 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
 21 36  1  0
 21 37  1  0
 24 38  1  0
 24 39  1  0
M  CHG  1   2   1
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       7.686  -1.537   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.577  -7.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.049  -6.833   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.991  -6.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.462  -6.281   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.030  -5.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.820  -3.137   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.233  -2.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.831  -3.098   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.423  -2.827   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.501  -5.785   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.914  -5.233   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.443  -5.417   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.896  -4.369   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.309  -3.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.857  -4.865   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.954  -4.737   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.349  -3.321   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.367  -4.185   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.780  -3.633   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.762  -2.769   0.000  0.00  0.00           N+1
HETATM   22  O   UNK     0       0.399  -4.367   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.488  -4.599   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.509  -2.308   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.894  -2.373   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3   11                                                       
CONECT    3    2   13                                                       
CONECT    4    5   12                                                       
CONECT    5    4   16                                                       
CONECT    6   11   17                                                       
CONECT    7   14   18                                                       
CONECT    8   15   21                                                       
CONECT    9   23   24                                                       
CONECT   10   22   25                                                       
CONECT   11    2    6   14                                                  
CONECT   12    4   13   15                                                  
CONECT   13    3   12   19                                                  
CONECT   14    7   11   19                                                  
CONECT   15    8   12   20                                                  
CONECT   16    5   20   22                                                  
CONECT   17    6   18   23                                                  
CONECT   18    7   17   24                                                  
CONECT   19   13   14   21                                                  
CONECT   20   15   16   25                                                  
CONECT   21    1    8   19                                                  
CONECT   22   10   16                                                       
CONECT   23    9   17                                                       
CONECT   24    9   18                                                       
CONECT   25   10   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

COMPND    HMDB0029367
HETATM    1  C1  UNL     1       0.554   2.275  -0.962  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.194   1.194  -0.436  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.568   1.331  -0.351  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.414   0.363   0.058  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.758   0.613   0.102  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.624  -0.375   0.519  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.114  -1.601   0.887  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.735  -1.866   0.845  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.919  -0.843   0.420  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.560  -1.033   0.357  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.020  -2.247   0.703  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.312  -2.516   0.658  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.132  -1.502   0.244  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.495  -1.758   0.221  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.376  -0.784  -0.157  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.926   0.452  -0.514  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.546   0.740  -0.499  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.671  -0.231  -0.128  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.290   0.006  -0.074  1.00  0.00           C  
HETATM   20  O1  UNL     1       4.991   1.248  -0.847  1.00  0.00           O  
HETATM   21  C19 UNL     1       6.170   0.574  -0.479  1.00  0.00           C  
HETATM   22  O2  UNL     1       5.763  -0.763  -0.273  1.00  0.00           O  
HETATM   23  O3  UNL     1      -5.899   0.151   0.463  1.00  0.00           O  
HETATM   24  C20 UNL     1      -5.807   1.559   0.286  1.00  0.00           C  
HETATM   25  O4  UNL     1      -4.498   1.758  -0.216  1.00  0.00           O  
HETATM   26  H1  UNL     1       1.030   2.126  -1.966  1.00  0.00           H  
HETATM   27  H2  UNL     1       0.979   3.015  -0.276  1.00  0.00           H  
HETATM   28  H3  UNL     1      -0.266   3.000  -1.399  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.957   2.314  -0.641  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.760  -2.407   1.222  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.404  -2.836   1.143  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.652  -3.049   1.030  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.695  -3.465   0.931  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.852  -2.731   0.502  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.311   1.701  -0.736  1.00  0.00           H  
HETATM   36  H11 UNL     1       6.963   0.654  -1.251  1.00  0.00           H  
HETATM   37  H12 UNL     1       6.601   0.964   0.470  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.946   2.062   1.251  1.00  0.00           H  
HETATM   39  H14 UNL     1      -6.564   1.902  -0.424  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3   19
CONECT    3    4   29
CONECT    4    5    5    9
CONECT    5    6   25
CONECT    6    7    7   23
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10
CONECT   10   11   11   19
CONECT   11   12   32
CONECT   12   13   13   33
CONECT   13   14   18
CONECT   14   15   15   34
CONECT   15   16   22
CONECT   16   17   17   20
CONECT   17   18   35
CONECT   18   19   19
CONECT   20   21
CONECT   21   22   36   37
CONECT   23   24
CONECT   24   25   38   39
END

HMDB0029367
     RDKit          3D
Sanguinarine
 39 44  0  0  0  0  0  0  0  0999 V2000
    0.5543    2.2754   -0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    1.1943   -0.4358 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5676    1.3315   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    0.3631    0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581    0.6129    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6235   -0.3747    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138   -1.6009    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354   -1.8660    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190   -0.8426    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -1.0327    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201   -2.2469    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -2.5156    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -1.5016    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4954   -1.7581    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762   -0.7842   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.4520   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    0.7403   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714   -0.2311   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2900    0.0064   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9915    1.2477   -0.8470 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1696    0.5740   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634   -0.7625   -0.2730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    0.1512    0.4625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8068    1.5592    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4983    1.7584   -0.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0303    2.1258   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    3.0149   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    3.0000   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569    2.3140   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7600   -2.4067    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -2.8362    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -3.0488    1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949   -3.4654    0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8516   -2.7306    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115    1.7013   -0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9628    0.6539   -1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6006    0.9635    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465    2.0625    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5641    1.9023   -0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  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
 16 20  1  0
 20 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  1  0
 24 25  1  0
 19  2  1  0
  9  4  1  0
 19 10  1  0
 25  5  1  0
 18 13  1  0
 22 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  7 30  1  0
  8 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
 21 36  1  0
 21 37  1  0
 24 38  1  0
 24 39  1  0
M  CHG  1   2   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium	ChEBI
13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9ci	HMDB
5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+)	HMDB
Benzophenanthridine alkaloid	HMDB
Dimethylenedioxy benzphenanthridine	HMDB
Pseudochelerythrine	HMDB
Sanguinarin	HMDB
Sanguinarine chloride	HMDB
Sanguinarium	HMDB
Sanguiritrin	HMDB
Sangvinarin	HMDB
Veadent	HMDB
Viadent	HMDB
Y-chelerythrine	HMDB
Pseudo-chelerythrine	HMDB
Sanguinarine sulfate (2:1)	HMDB
Sanguinarine sulfate (1:1)	HMDB
Sanguinarine hydroxide	HMDB
Sanguinarine nitrate	HMDB

Chemical Formula

C₂₀H₁₄NO₄

Average Molecular Weight

332.3295

Monoisotopic Molecular Weight

332.092282941

IUPAC Name

24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaen-24-ium

Traditional Name

sanguinarine

CAS Registry Number

2447-54-3

SMILES

C[N+]1=C2C3=CC4=C(OCO4)C=C3C=CC2=C2C=CC3=C(OCO3)C2=C1

InChI Identifier

InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1

InChI Key

INVGWHRKADIJHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quaternary benzophenanthridine alkaloids. These are alkaloids containing a quaternary N-demethylbenzophenanthridine skeleton, where the nitrogen atom of the phenanthridine moiety is part of four bonds.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Quaternary benzophenanthridine alkaloids

Direct Parent

Quaternary benzophenanthridine alkaloids

Alternative Parents

Substituents

Quaternary benzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Isoquinoline
Naphthalene
Quinoline
Benzodioxole
Pyridine
Benzenoid
Pyridinium
Heteroaromatic compound
Azacycle
Oxacycle
Acetal
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzophenanthridine alkaloid (CHEBI:17183 )
alkaloid antibiotic (CHEBI:17183 )
botanical anti-fungal agent (CHEBI:17183 )
Isoquinoline alkaloids (C06162 )
a small molecule (SANGUINARINE )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	266 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.32 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.653 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00019 g/L	ALOGPS
logP	-0.51	ALOGPS
logP	-0.94	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.8 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.82 m³·mol⁻¹	ChemAxon
Polarizability	35.62 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	176.31	30932474
DeepCCS	[M-H]-	173.952	30932474
DeepCCS	[M-2H]-	207.456	30932474
DeepCCS	[M+Na]+	182.684	30932474
AllCCS	[M+H]+	177.3	32859911
AllCCS	[M+H-H2O]+	173.9	32859911
AllCCS	[M+NH4]+	180.4	32859911
AllCCS	[M+Na]+	181.3	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	184.8	32859911
AllCCS	[M+HCOO]-	184.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sanguinarine	C[N+]1=C2C3=CC4=C(OCO4)C=C3C=CC2=C2C=CC3=C(OCO3)C2=C1	4470.4	Standard polar	33892256
Sanguinarine	C[N+]1=C2C3=CC4=C(OCO4)C=C3C=CC2=C2C=CC3=C(OCO3)C2=C1	2996.1	Standard non polar	33892256
Sanguinarine	C[N+]1=C2C3=CC4=C(OCO4)C=C3C=CC2=C2C=CC3=C(OCO3)C2=C1	3476.2	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 - Sanguinarine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0019000000-00748d09c91de933d22a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sanguinarine 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 - Sanguinarine LC-ESI-QQ , positive-QTOF	splash10-0fz9-0089000000-f8aef246d6f8f144f417	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sanguinarine LC-ESI-QQ , positive-QTOF	splash10-01ba-0093000000-8e78de64c96cdc678a00	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sanguinarine LC-ESI-QQ , positive-QTOF	splash10-001i-0009000000-136b5256b656b11c43ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sanguinarine LC-ESI-QQ , positive-QTOF	splash10-001i-0009000000-908c2e468892ac93bbe7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sanguinarine LC-ESI-QQ , positive-QTOF	splash10-001i-0049000000-b15f0155462f7f9e3ab5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sanguinarine LC-ESI-QQ , positive-QTOF	splash10-01ba-0092000000-d8d44b51327d3e8b0a71	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sanguinarine LC-ESI-IT , positive-QTOF	splash10-0udi-0039000000-c85daa2f888c3a5c8e7f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sanguinarine , positive-QTOF	splash10-00lr-0397000000-57df1e4d4f5d79d09336	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 10V, Positive-QTOF	splash10-001i-0009000000-2ad2cccd8ab76cdff89f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 20V, Positive-QTOF	splash10-001i-0009000000-463ec0488cc6bf1210ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 40V, Positive-QTOF	splash10-0wt9-0079000000-e461a044f76d24fe94ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 10V, Negative-QTOF	splash10-001i-0009000000-156aaa823d56af69fe05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 20V, Negative-QTOF	splash10-001i-0009000000-1affdcdb9daee140befd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 40V, Negative-QTOF	splash10-003r-2089000000-f131958bee2ac1fc2c87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 10V, Positive-QTOF	splash10-001i-0009000000-135a15e661484c68a718	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 20V, Positive-QTOF	splash10-001i-0009000000-18ac2ce9064730020599	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sanguinarine 40V, Positive-QTOF	splash10-0udi-0019000000-f7f1076878f20b9585fe	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sanguinarine

METLIN ID

Not Available

PubChem Compound

5154

PDB ID

ChEBI ID

17183

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1665421

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Eun JP, Koh GY: Suppression of angiogenesis by the plant alkaloid, sanguinarine. Biochem Biophys Res Commun. 2004 Apr 30;317(2):618-24. [PubMed:15063803 ]
Weerasinghe P, Hallock S, Tang SC, Liepins A: Sanguinarine induces bimodal cell death in K562 but not in high Bcl-2-expressing JM1 cells. Pathol Res Pract. 2001;197(11):717-26. [PubMed:11770015 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Sanguinarine (HMDB0029367)

MOL for HMDB0029367 (Sanguinarine)

3D MOL for HMDB0029367 (Sanguinarine)

3D SDF for HMDB0029367 (Sanguinarine)

3D-SDF for HMDB0029367 (Sanguinarine)

PDB for HMDB0029367 (Sanguinarine)

3D PDB for HMDB0029367 (Sanguinarine)

SMILES for HMDB0029367 (Sanguinarine)

INCHI for HMDB0029367 (Sanguinarine)

Structure for HMDB0029367 (Sanguinarine)

3D Structure for HMDB0029367 (Sanguinarine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra