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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:17 UTC

Update Date

2022-03-07 02:52:27 UTC

HMDB ID

HMDB0030176

Secondary Accession Numbers

HMDB30176

Metabolite Identification

Common Name

Norsanguinarine

Description

Norsanguinarine, also known as 2,3, belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. Based on a literature review a significant number of articles have been published on Norsanguinarine.

Structure

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

HMDB0030176
     RDKit          3D
Norsanguinarine
 35 40  0  0  0  0  0  0  0  0999 V2000
    4.0436   -1.4740    0.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6679   -1.6802    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -0.6587    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951    0.5902   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    1.6075   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005    1.4223   -0.4528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.2361   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490    0.0577   -0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649    1.0950   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9495    0.9245   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5020   -0.2928   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933   -1.3480   -0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -1.1728    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -2.2263    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -2.0427    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4602   -0.8334    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8971   -0.1764   -0.5310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1744    1.1876   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9650    1.8073   -0.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.8061   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5778   -0.2435    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8762    0.2696    0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767    1.6833    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    1.9436   -0.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7161   -2.2729    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -2.6374    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    2.5725   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    2.0610   -0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1355   -2.3196    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -3.1821    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -2.8838    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9321    1.4591   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5202    1.6290    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6220    2.0949   -0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7955    1.9972    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
  4 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21  1  1  0
 16  3  1  0
 24 20  1  0
 16  7  1  0
 13  8  1  0
 19 10  1  0
  1 25  1  0
  2 26  1  0
  5 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 23 34  1  0
 23 35  1  0
M  END


  Mrv1652309152018092D          

 24 29  0  0  0  0            999 V2000
 9998.5796 9999.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5796 9998.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2910 9999.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2910 9998.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0055 9998.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7200 9998.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.718110001.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.003710000.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0037 9999.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7181 9999.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.858310000.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.143910001.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.429410000.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4293 9999.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1438 9999.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8584 9999.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0806 9999.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5957 9998.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0806 9998.2938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8652 9998.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8652 9999.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.471510001.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.136010001.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.315510001.8394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  9 10  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  2  4  1  0  0  0  0
  3  1  1  0  0  0  0
  6 10  1  0  0  0  0
  9  3  1  0  0  0  0
 10 14  1  0  0  0  0
 13  7  1  0  0  0  0
 20 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 21  2  0  0  0  0
 20  2  2  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 22 23  1  0  0  0  0
 11 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030176

> <DATABASE_NAME>
hmdb

> <SMILES>
C1OC2=CC3=C(C=C2O1)C1=C(C=C3)C2=C(C=N1)C1=C(OCO1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H11NO4/c1-2-12-11-3-4-15-19(24-9-21-15)14(11)7-20-18(12)13-6-17-16(5-10(1)13)22-8-23-17/h1-7H,8-9H2

> <INCHI_KEY>
CNXVDVMAYXLWPD-UHFFFAOYSA-N

> <FORMULA>
C19H11NO4

> <MOLECULAR_WEIGHT>
317.2949

> <EXACT_MASS>
317.068807845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
33.16821750917947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
3.35632092

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.48913261823956

> <JCHEM_POLAR_SURFACE_AREA>
49.81

> <JCHEM_REFRACTIVITY>
84.4135

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030176
     RDKit          3D
Norsanguinarine
 35 40  0  0  0  0  0  0  0  0999 V2000
    4.0436   -1.4740    0.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6679   -1.6802    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -0.6587    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951    0.5902   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    1.6075   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005    1.4223   -0.4528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.2361   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490    0.0577   -0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649    1.0950   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9495    0.9245   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5020   -0.2928   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933   -1.3480   -0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -1.1728    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -2.2263    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -2.0427    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4602   -0.8334    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8971   -0.1764   -0.5310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1744    1.1876   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9650    1.8073   -0.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.8061   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5778   -0.2435    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8762    0.2696    0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767    1.6833    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    1.9436   -0.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7161   -2.2729    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -2.6374    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    2.5725   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    2.0610   -0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1355   -2.3196    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -3.1821    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -2.8838    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9321    1.4591   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5202    1.6290    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6220    2.0949   -0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7955    1.9972    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
  4 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21  1  1  0
 16  3  1  0
 24 20  1  0
 16  7  1  0
 13  8  1  0
 19 10  1  0
  1 25  1  0
  2 26  1  0
  5 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 23 34  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  C   UNK     0    8664.0158666.268   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0158663.187   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.3438665.497   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.3438663.958   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.6778663.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.0118663.958   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.0078668.592   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8666.6748667.822   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    8666.6748666.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0078665.512   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.0028667.824   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.6698668.594   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.3358667.824   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.3358666.284   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.6688665.514   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8672.0028666.284   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8661.2178665.974   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8660.3128664.728   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8661.2178663.482   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8662.6828663.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8662.6828665.498   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8673.1478668.854   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8672.5218670.261   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8670.9898670.100   0.000  0.00  0.00           O+0
CONECT    1    3   21                                                       
CONECT    2    4   20                                                       
CONECT    3    4    1    9                                                  
CONECT    4    3    5    2                                                  
CONECT    5    4    6                                                       
CONECT    6    5   10                                                       
CONECT    7    8   13                                                       
CONECT    8    7    9                                                       
CONECT    9   10    8    3                                                  
CONECT   10    9    6   14                                                  
CONECT   11   12   16   22                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14    7                                                  
CONECT   14   13   15   10                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   18   21                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   21   19    2                                                  
CONECT   21   20   17    1                                                  
CONECT   22   23   11                                                       
CONECT   23   24   22                                                       
CONECT   24   23   12                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

COMPND    HMDB0030176
HETATM    1  C1  UNL     1       4.044  -1.474   0.621  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.668  -1.680   0.563  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.816  -0.659   0.225  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.395   0.590  -0.055  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.529   1.608  -0.393  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.200   1.422  -0.453  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.377   0.236  -0.189  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.749   0.058  -0.254  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.565   1.095  -0.593  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.950   0.925  -0.661  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.502  -0.293  -0.387  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.693  -1.348  -0.044  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.305  -1.173   0.024  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.501  -2.226   0.366  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.123  -2.043   0.430  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.460  -0.833   0.160  1.00  0.00           C  
HETATM   17  O1  UNL     1      -5.897  -0.176  -0.531  1.00  0.00           O  
HETATM   18  C16 UNL     1      -6.174   1.188  -0.591  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.965   1.807  -0.976  1.00  0.00           O  
HETATM   20  C17 UNL     1       3.756   0.806  -0.001  1.00  0.00           C  
HETATM   21  C18 UNL     1       4.578  -0.243   0.342  1.00  0.00           C  
HETATM   22  O3  UNL     1       5.876   0.270   0.313  1.00  0.00           O  
HETATM   23  C19 UNL     1       5.777   1.683   0.381  1.00  0.00           C  
HETATM   24  O4  UNL     1       4.521   1.944  -0.237  1.00  0.00           O  
HETATM   25  H1  UNL     1       4.716  -2.273   0.886  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.295  -2.637   0.784  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.996   2.573  -0.608  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.143   2.061  -0.812  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.136  -2.320   0.175  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.950  -3.182   0.580  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.438  -2.884   0.697  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.932   1.459  -1.352  1.00  0.00           H  
HETATM   33  H9  UNL     1      -6.520   1.629   0.364  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.622   2.095  -0.207  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.796   1.997   1.432  1.00  0.00           H  
CONECT    1    2    2   21   25
CONECT    2    3   26
CONECT    3    4    4   16
CONECT    4    5   20
CONECT    5    6    6   27
CONECT    6    7
CONECT    7    8    8   16
CONECT    8    9   13
CONECT    9   10   10   28
CONECT   10   11   19
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   14
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   17   18
CONECT   18   19   32   33
CONECT   20   21   21   24
CONECT   21   22
CONECT   22   23
CONECT   23   24   34   35
END

HMDB0030176
     RDKit          3D
Norsanguinarine
 35 40  0  0  0  0  0  0  0  0999 V2000
    4.0436   -1.4740    0.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6679   -1.6802    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -0.6587    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951    0.5902   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    1.6075   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005    1.4223   -0.4528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.2361   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490    0.0577   -0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649    1.0950   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9495    0.9245   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5020   -0.2928   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933   -1.3480   -0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -1.1728    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -2.2263    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227   -2.0427    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4602   -0.8334    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8971   -0.1764   -0.5310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1744    1.1876   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9650    1.8073   -0.9755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.8061   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5778   -0.2435    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8762    0.2696    0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767    1.6833    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    1.9436   -0.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7161   -2.2729    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -2.6374    0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    2.5725   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    2.0610   -0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1355   -2.3196    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9501   -3.1821    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -2.8838    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9321    1.4591   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5202    1.6290    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6220    2.0949   -0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7955    1.9972    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
  4 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21  1  1  0
 16  3  1  0
 24 20  1  0
 16  7  1  0
 13  8  1  0
 19 10  1  0
  1 25  1  0
  2 26  1  0
  5 27  1  0
  9 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 23 34  1  0
 23 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-I)phenanthridine	HMDB
1,3-Dioxolo(I)(1,3)dioxolo(4,5)benzo(1,2-c)phenanthridine	HMDB
1,3-Dioxolo[I][1,3]dioxolo[4,5]benzo[1,2-c]phenanthridine	HMDB
13-Demethyl-sanguinarine	HMDB
2,3	HMDB
7,8-Bis(methylenedioxy)benzo[c]phenanthridine	HMDB
Dihydrosanguinarine	HMDB
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-I]phenanthridine	HMDB
13-Demethylsanguinarine	HMDB
Demethylsanguinarine	HMDB
N-Norsanguinarine	HMDB
Norsanguinarine	MeSH

Chemical Formula

C₁₉H₁₁NO₄

Average Molecular Weight

317.2949

Monoisotopic Molecular Weight

317.068807845

IUPAC Name

5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene

Traditional Name

5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene

CAS Registry Number

522-30-5

SMILES

C1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C2

InChI Identifier

InChI=1S/C19H11NO4/c1-2-12-11-3-4-15-19(24-9-21-15)14(11)7-20-18(12)13-6-17-16(5-10(1)13)22-8-23-17/h1-7H,8-9H2

InChI Key

CNXVDVMAYXLWPD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Isoquinoline
Naphthalene
Benzodioxole
Pyridine
Benzenoid
Heteroaromatic compound
Azacycle
Acetal
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030176)
Cell membrane (HMDB: HMDB0030176)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030176)

Source

Endogenous

Endogenous (HMDB: HMDB0030176)

Plant

Plant (HMDB: HMDB0030176)

Exogenous

Food

Food (HMDB: HMDB0030176)

Herb and spice

Spice

Opium poppy (FooDB: FOOD00438)

Exogenous (HMDB: HMDB0030176)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285 - 287 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.61	ALOGPS
logP	3.36	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	4.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.81 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.41 m³·mol⁻¹	ChemAxon
Polarizability	33.17 Å³	ChemAxon
Number of Rings	6	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]+	170.577	31661259
DarkChem	[M-H]-	174.76	31661259
DeepCCS	[M-2H]-	220.004	30932474
DeepCCS	[M+Na]+	195.677	30932474
AllCCS	[M+H]+	174.1	32859911
AllCCS	[M+H-H2O]+	170.5	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.3	32859911
AllCCS	[M-H]-	178.1	32859911
AllCCS	[M+Na-2H]-	176.6	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.53 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8366 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.69 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	66.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2097.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	307.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	113.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	553.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	568.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	195.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	867.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	473.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1816.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	471.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	355.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	59.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norsanguinarine	C1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C2	4405.6	Standard polar	33892256
Norsanguinarine	C1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C2	2896.3	Standard non polar	33892256
Norsanguinarine	C1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C2	3407.6	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 - Norsanguinarine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1289000000-030ebf995d568cd09ccd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norsanguinarine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 10V, Positive-QTOF	splash10-014i-0009000000-d38f3b692115364c5b2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 20V, Positive-QTOF	splash10-014i-0009000000-b0a36b2176aa875f1d56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 40V, Positive-QTOF	splash10-00di-0092000000-70928fb95ffcf8e3f05b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 10V, Negative-QTOF	splash10-014i-0009000000-7997eb6006f3e07da70c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 20V, Negative-QTOF	splash10-014i-0009000000-fd34fc3396df9b21bbed	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 40V, Negative-QTOF	splash10-01b9-0079000000-5c74b62bff7c51937be9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 10V, Negative-QTOF	splash10-014i-0009000000-cdb697e9f2878552c94c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 20V, Negative-QTOF	splash10-014i-0029000000-510145a97d282a2483bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 40V, Negative-QTOF	splash10-000i-0091000000-961350d21ad47df1f439	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 10V, Positive-QTOF	splash10-014i-0009000000-7a22534e87f602b14ab3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 20V, Positive-QTOF	splash10-014i-0019000000-a616b24aed205ed9252c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsanguinarine 40V, Positive-QTOF	splash10-0006-0090000000-328d9a56a7c6e865c9de	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

Not Available

METLIN ID

Not Available

PubChem Compound

97679

PDB ID

Not Available

ChEBI ID

17209

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 Norsanguinarine (HMDB0030176)

MOL for HMDB0030176 (Norsanguinarine)

3D MOL for HMDB0030176 (Norsanguinarine)

3D SDF for HMDB0030176 (Norsanguinarine)

3D-SDF for HMDB0030176 (Norsanguinarine)

PDB for HMDB0030176 (Norsanguinarine)

3D PDB for HMDB0030176 (Norsanguinarine)

SMILES for HMDB0030176 (Norsanguinarine)

INCHI for HMDB0030176 (Norsanguinarine)

Structure for HMDB0030176 (Norsanguinarine)

3D Structure for HMDB0030176 (Norsanguinarine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra