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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:42:22 UTC

Update Date

2021-09-26 23:15:06 UTC

HMDB ID

HMDB0258305

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sinomenine

Description

3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5,11-tetraen-13-one belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Based on a literature review very few articles have been published on 3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5,11-tetraen-13-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Sinomenine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Sinomenine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258305
     RDKit          3D
Sinomenine
 47 50  0  0  0  0  0  0  0  0999 V2000
   -4.0137    3.3625    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    2.6687   -0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2340    1.6687    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815    0.4212   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610   -0.7197    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2319   -1.6811   -0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5810   -0.8029   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264   -0.1606   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555    0.1860   -2.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    0.7754   -1.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599    0.9975   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0345    1.6037    0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0890    1.9660   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358    0.6522    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    0.9357    1.9078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    0.0640    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893   -0.2981    1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.5687    1.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721   -2.7066    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4471   -2.7626   -0.3736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554   -4.0306   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    0.7584    1.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3001    1.9264    1.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    3.0906    1.4184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4174    4.1007   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8470    2.6675    0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076    3.8964    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619    0.2194   -1.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997   -1.2217    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1706   -2.0621   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -0.0028   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022   -1.3763   -2.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062    0.0128   -3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5945    1.0490   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291    1.0907   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7173    2.5572   -1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638    2.6537   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    1.3657    2.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -1.8187    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546   -1.4049    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735   -3.6563    1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -2.7731    0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3045   -4.4410    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1304   -3.8551   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5100   -4.7509   -1.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784    0.3241    2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    1.0797    2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 23  3  1  0
 17  5  1  0
 20  6  1  0
 16  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END

  Mrv1533004241502172D          

 24 27  0  0  0  0            999 V2000
    3.4441   -0.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255   -0.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8552    0.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1092   -0.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -0.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1944    0.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281   -0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813    1.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747    1.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0085    1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475    1.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    2.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    1.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146    1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    1.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647    1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2050    0.1990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5408   -0.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    1.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    1.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883    1.5889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258305

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2C3CC4=CC=C(OC)C(O)=C4C2(CCN3C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3

> <INCHI_KEY>
INYYVPJSBIVGPH-UHFFFAOYSA-N

> <FORMULA>
C19H23NO4

> <MOLECULAR_WEIGHT>
329.396

> <EXACT_MASS>
329.162708225

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.30491661258518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,11-tetraen-13-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.4476778569943256

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.838554552671848

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.832212233116003

> <JCHEM_PKA_STRONGEST_BASIC>
8.271200100287679

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
92.99739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sinomenine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258305
     RDKit          3D
Sinomenine
 47 50  0  0  0  0  0  0  0  0999 V2000
   -4.0137    3.3625    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    2.6687   -0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2340    1.6687    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815    0.4212   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610   -0.7197    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2319   -1.6811   -0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5810   -0.8029   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264   -0.1606   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555    0.1860   -2.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    0.7754   -1.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599    0.9975   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0345    1.6037    0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0890    1.9660   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358    0.6522    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    0.9357    1.9078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    0.0640    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893   -0.2981    1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.5687    1.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721   -2.7066    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4471   -2.7626   -0.3736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554   -4.0306   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    0.7584    1.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3001    1.9264    1.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    3.0906    1.4184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4174    4.1007   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8470    2.6675    0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076    3.8964    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619    0.2194   -1.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997   -1.2217    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1706   -2.0621   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -0.0028   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022   -1.3763   -2.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062    0.0128   -3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5945    1.0490   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291    1.0907   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7173    2.5572   -1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638    2.6537   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    1.3657    2.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -1.8187    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546   -1.4049    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735   -3.6563    1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -2.7731    0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3045   -4.4410    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1304   -3.8551   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5100   -4.7509   -1.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784    0.3241    2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    1.0797    2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 23  3  1  0
 17  5  1  0
 20  6  1  0
 16  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.429  -1.632   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.581  -0.099   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.330   0.799   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.937  -0.053   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.675   1.062   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.524  -0.663   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.062  -0.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.096   0.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.466  -0.151   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.760   0.684   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.685   2.222   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.979   3.056   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.349   2.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.315   2.926   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.240   4.464   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.021   2.091   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.827   2.594   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.342   3.051   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.307   1.910   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.383   0.372   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -1.010  -0.287   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.230   3.229   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.482   2.331   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.885   2.966   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16    5   18   22                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    6   21                                                  
CONECT   21   20                                                            
CONECT   22   17   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0258305
HETATM    1  C1  UNL     1      -4.014   3.362   0.056  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.953   2.669  -0.554  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.234   1.669   0.073  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.381   0.421  -0.314  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.661  -0.720   0.290  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.232  -1.681  -0.787  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.581  -0.803  -1.864  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.626  -0.161  -1.277  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.656   0.186  -2.146  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.793   0.775  -1.645  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.860   0.998  -0.290  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.034   1.604   0.209  1.00  0.00           O  
HETATM   13  C11 UNL     1       5.089   1.966  -0.630  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.836   0.652   0.571  1.00  0.00           C  
HETATM   15  O3  UNL     1       2.046   0.936   1.908  1.00  0.00           O  
HETATM   16  C13 UNL     1       0.695   0.064   0.089  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.389  -0.298   1.018  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.062  -1.569   1.736  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.272  -2.707   0.826  1.00  0.00           C  
HETATM   20  N1  UNL     1      -0.447  -2.763  -0.374  1.00  0.00           N  
HETATM   21  C17 UNL     1      -1.155  -4.031  -0.546  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.804   0.758   1.977  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.300   1.926   1.165  1.00  0.00           C  
HETATM   24  O4  UNL     1      -0.923   3.091   1.418  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.417   4.101  -0.644  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.847   2.667   0.364  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.608   3.896   0.940  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.062   0.219  -1.111  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.300  -1.222   1.036  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.171  -2.062  -1.264  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.290  -0.003  -2.100  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.302  -1.376  -2.748  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.606   0.013  -3.212  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.595   1.049  -2.297  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.629   1.091  -1.022  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.717   2.557  -1.506  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.764   2.654  -0.080  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.885   1.366   2.247  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.783  -1.819   2.434  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.955  -1.405   2.355  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.074  -3.656   1.407  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.376  -2.773   0.596  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.305  -4.441   0.491  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.130  -3.855  -1.035  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.510  -4.751  -1.077  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.678   0.324   2.550  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.091   1.080   2.722  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6   17   29
CONECT    6    7   20   30
CONECT    7    8   31   32
CONECT    8    9    9   16
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   12   14
CONECT   12   13
CONECT   13   35   36   37
CONECT   14   15   16   16
CONECT   15   38
CONECT   16   17
CONECT   17   18   22
CONECT   18   19   39   40
CONECT   19   20   41   42
CONECT   20   21
CONECT   21   43   44   45
CONECT   22   23   46   47
CONECT   23   24   24
END

HMDB0258305
     RDKit          3D
Sinomenine
 47 50  0  0  0  0  0  0  0  0999 V2000
   -4.0137    3.3625    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    2.6687   -0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2340    1.6687    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815    0.4212   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610   -0.7197    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2319   -1.6811   -0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5810   -0.8029   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264   -0.1606   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555    0.1860   -2.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    0.7754   -1.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599    0.9975   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0345    1.6037    0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0890    1.9660   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358    0.6522    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    0.9357    1.9078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    0.0640    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3893   -0.2981    1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.5687    1.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721   -2.7066    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4471   -2.7626   -0.3736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554   -4.0306   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    0.7584    1.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3001    1.9264    1.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    3.0906    1.4184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4174    4.1007   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8470    2.6675    0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076    3.8964    0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619    0.2194   -1.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997   -1.2217    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1706   -2.0621   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -0.0028   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3022   -1.3763   -2.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062    0.0128   -3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5945    1.0490   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291    1.0907   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7173    2.5572   -1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638    2.6537   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    1.3657    2.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -1.8187    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546   -1.4049    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735   -3.6563    1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -2.7731    0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3045   -4.4410    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1304   -3.8551   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5100   -4.7509   -1.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784    0.3241    2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    1.0797    2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 23  3  1  0
 17  5  1  0
 20  6  1  0
 16  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃NO₄

Average Molecular Weight

329.396

Monoisotopic Molecular Weight

329.162708225

IUPAC Name

3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,11-tetraen-13-one

Traditional Name

sinomenine

CAS Registry Number

Not Available

SMILES

COC1=CC2C3CC4=CC=C(OC)C(O)=C4C2(CCN3C)CC1=O

InChI Identifier

InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3

InChI Key

INYYVPJSBIVGPH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Benzazocine
Isoquinolone
Tetralin
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Piperidine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Azacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0258305)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	1.89	ALOGPS
logP	1.45	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93 m³·mol⁻¹	ChemAxon
Polarizability	35.3 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M+H]+	179.163	30932474
DeepCCS	[M-H]-	176.805	30932474
DeepCCS	[M-2H]-	209.691	30932474
DeepCCS	[M+Na]+	185.257	30932474
AllCCS	[M+H]+	179.5	32859911
AllCCS	[M+H-H2O]+	176.5	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	182.0	32859911
AllCCS	[M+Na-2H]-	181.9	32859911
AllCCS	[M+HCOO]-	181.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sinomenine	COC1=CC2C3CC4=CC=C(OC)C(O)=C4C2(CCN3C)CC1=O	4128.9	Standard polar	33892256
Sinomenine	COC1=CC2C3CC4=CC=C(OC)C(O)=C4C2(CCN3C)CC1=O	2620.0	Standard non polar	33892256
Sinomenine	COC1=CC2C3CC4=CC=C(OC)C(O)=C4C2(CCN3C)CC1=O	2789.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sinomenine,2TMS,isomer #1	COC1=CC2C3CC4=CC=C(OC)C(O[Si](C)(C)C)=C4C2(C=C1O[Si](C)(C)C)CCN3C	2784.5	Semi standard non polar	33892256
Sinomenine,2TMS,isomer #1	COC1=CC2C3CC4=CC=C(OC)C(O[Si](C)(C)C)=C4C2(C=C1O[Si](C)(C)C)CCN3C	2734.6	Standard non polar	33892256
Sinomenine,2TMS,isomer #1	COC1=CC2C3CC4=CC=C(OC)C(O[Si](C)(C)C)=C4C2(C=C1O[Si](C)(C)C)CCN3C	3368.7	Standard polar	33892256
Sinomenine,2TBDMS,isomer #1	COC1=CC2C3CC4=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C4C2(C=C1O[Si](C)(C)C(C)(C)C)CCN3C	3205.9	Semi standard non polar	33892256
Sinomenine,2TBDMS,isomer #1	COC1=CC2C3CC4=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C4C2(C=C1O[Si](C)(C)C(C)(C)C)CCN3C	3144.6	Standard non polar	33892256
Sinomenine,2TBDMS,isomer #1	COC1=CC2C3CC4=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C4C2(C=C1O[Si](C)(C)C(C)(C)C)CCN3C	3593.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sinomenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gw4-0092000000-0b9866d45f769eba2f96	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinomenine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinomenine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinomenine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinomenine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinomenine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-001i-0019000000-cde3db4eb2df95854c32	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Negative-QTOF	splash10-03fr-0229000000-a66a951dfe02b8b68f33	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-004i-0009000000-c533e5496ed10ef47802	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-03di-0079000000-5daa292d083440a27a37	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-03di-0930000000-b53cdd180086950bcbe3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-0096-0592000000-32e557debb457f7faa96	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-03gl-0294000000-420ec280e67c35978ded	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 10V, Positive-QTOF	splash10-001i-0009000000-2b9fade5282ff5b389d2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 20V, Positive-QTOF	splash10-001i-0079000000-2680a3a6c0c8a3090fc9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-01ot-0491000000-8360e058d8f97be7942f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-000t-1900000000-6fc85e5ed9ad24a03894	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-004i-0059000000-7fb35e9d8b213c892b00	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-000t-0900000000-2fdd2eeb00f598561866	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-001i-0019000000-1bf3898038ef29577706	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-004i-0009000000-2e8a5b33dea022402438	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinomenine 6V, Positive-QTOF	splash10-004i-0009000000-216c18bc933d02a1fa57	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

368395

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

416119

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Sinomenine (HMDB0258305)

MOL for HMDB0258305 (Sinomenine)

3D MOL for HMDB0258305 (Sinomenine)

3D SDF for HMDB0258305 (Sinomenine)

3D-SDF for HMDB0258305 (Sinomenine)

PDB for HMDB0258305 (Sinomenine)

3D PDB for HMDB0258305 (Sinomenine)

SMILES for HMDB0258305 (Sinomenine)

INCHI for HMDB0258305 (Sinomenine)

Structure for HMDB0258305 (Sinomenine)

3D Structure for HMDB0258305 (Sinomenine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra