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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:10:23 UTC

Update Date

2021-09-26 23:07:47 UTC

HMDB ID

HMDB0254050

Secondary Accession Numbers

None

Metabolite Identification

Common Name

levo-tetrahydropalmatine

Description

levo-tetrahydropalmatine belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. Based on a literature review a significant number of articles have been published on levo-tetrahydropalmatine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Levo-tetrahydropalmatine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically levo-tetrahydropalmatine 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

HMDB0254050
     RDKit          3D
levo-tetrahydropalmatine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.8027   -0.4540    2.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    0.2308    1.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.3165    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791   -1.5952    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -2.1575    0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -1.4605   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540   -0.2164   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1093    0.3829   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.6388   -0.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3950    1.7351   -1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612    0.5278   -1.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742    0.1666   -1.6690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    1.0304   -2.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1512    1.4412   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    0.6613    0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7808    1.1603    1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.5029    2.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753   -0.6750    2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879   -1.1510    1.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.5163    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6594   -0.9861   -1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6459   -2.0478   -0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0438   -1.4566    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120   -0.6126    3.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7351    0.1040    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -2.1133    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0378   -3.1315    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    2.4404   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    0.7586   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    2.0326   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2309    1.6176   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.4998   -2.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472    1.8961   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.4775   -3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043    2.5119   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1863    1.3296   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3525    2.0859    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241    0.8834    3.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0669   -1.1974    3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -2.0540    1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416   -1.4508   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -2.8758   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -2.4767   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 21 12  1  0
 22  6  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

  Mrv1652309112115102D          

 22 25  0  0  0  0            999 V2000
   -2.1604   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203   -3.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -3.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5908   -3.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -4.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -4.3914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -4.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.4827    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254050

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(CC3N(CCC4=CC=CC=C34)C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO2/c1-21-18-8-7-14-11-17-15-6-4-3-5-13(15)9-10-20(17)12-16(14)19(18)22-2/h3-8,17H,9-12H2,1-2H3

> <INCHI_KEY>
PRDNGFIKZARQQH-UHFFFAOYSA-N

> <FORMULA>
C19H21NO2

> <MOLECULAR_WEIGHT>
295.382

> <EXACT_MASS>
295.15722892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.82335751019127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
3.463317251666667

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.013758659036466

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
88.4291

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254050
     RDKit          3D
levo-tetrahydropalmatine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.8027   -0.4540    2.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    0.2308    1.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.3165    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791   -1.5952    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -2.1575    0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -1.4605   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540   -0.2164   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1093    0.3829   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.6388   -0.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3950    1.7351   -1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612    0.5278   -1.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742    0.1666   -1.6690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    1.0304   -2.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1512    1.4412   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    0.6613    0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7808    1.1603    1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.5029    2.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753   -0.6750    2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879   -1.1510    1.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.5163    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6594   -0.9861   -1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6459   -2.0478   -0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0438   -1.4566    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120   -0.6126    3.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7351    0.1040    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -2.1133    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0378   -3.1315    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    2.4404   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    0.7586   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    2.0326   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2309    1.6176   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.4998   -2.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472    1.8961   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.4775   -3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043    2.5119   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1863    1.3296   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3525    2.0859    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241    0.8834    3.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0669   -1.1974    3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -2.0540    1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416   -1.4508   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -2.8758   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -2.4767   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 21 12  1  0
 22  6  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -4.033  -5.578   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.024  -6.742   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.512  -6.451   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.504  -7.615   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.008  -7.324   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.512  -5.869   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.024  -5.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.033  -6.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.545  -6.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.049  -4.996   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.561  -4.705   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.569  -5.869   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.065  -7.324   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.553  -7.615   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.049  -9.070   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.537  -9.361   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.529  -8.197   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.016  -8.488   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.504  -4.705   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.008  -4.996   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.008  -9.070   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000 -10.234   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    5                                                       
CONECT   19    6   20                                                       
CONECT   20   19    3                                                       
CONECT   21    4   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0254050
HETATM    1  C1  UNL     1       4.803  -0.454   2.245  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.009   0.231   1.307  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.859  -0.317   0.789  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.479  -1.595   1.216  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.329  -2.158   0.706  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.581  -1.460  -0.206  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.954  -0.216  -0.620  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.109   0.383  -0.126  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.532   1.639  -0.511  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.395   1.735  -1.625  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.161   0.528  -1.589  1.00  0.00           C  
HETATM   12  N1  UNL     1      -1.174   0.167  -1.669  1.00  0.00           N  
HETATM   13  C10 UNL     1      -2.118   1.030  -2.240  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.151   1.441  -1.226  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.086   0.661   0.037  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.781   1.160   1.118  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.784   0.503   2.349  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.075  -0.675   2.489  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.388  -1.151   1.385  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.379  -0.516   0.180  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.659  -0.986  -1.028  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.646  -2.048  -0.759  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.044  -1.457   1.813  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.212  -0.613   3.170  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.735   0.104   2.447  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.098  -2.113   1.939  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.038  -3.131   1.030  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.217   2.440  -1.412  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.887   0.759  -1.863  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.858   2.033  -2.547  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.231   1.618  -1.303  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.622   0.500  -2.621  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.647   1.896  -2.732  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.651   0.477  -3.069  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.004   2.512  -0.977  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.186   1.330  -1.652  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.353   2.086   1.052  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.324   0.883   3.205  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.067  -1.197   3.436  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.847  -2.054   1.498  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.442  -1.451  -1.694  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.026  -2.876  -0.176  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.364  -2.477  -1.767  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   22
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   28   29   30
CONECT   11   12   31   32
CONECT   12   13   21
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   16   20
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19   39
CONECT   19   20   20   40
CONECT   20   21
CONECT   21   22   41
CONECT   22   42   43
END

HMDB0254050
     RDKit          3D
levo-tetrahydropalmatine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.8027   -0.4540    2.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    0.2308    1.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -0.3165    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791   -1.5952    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -2.1575    0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -1.4605   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540   -0.2164   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1093    0.3829   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.6388   -0.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3950    1.7351   -1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612    0.5278   -1.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742    0.1666   -1.6690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    1.0304   -2.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1512    1.4412   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    0.6613    0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7808    1.1603    1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7837    0.5029    2.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753   -0.6750    2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879   -1.1510    1.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.5163    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6594   -0.9861   -1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6459   -2.0478   -0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0438   -1.4566    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120   -0.6126    3.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7351    0.1040    2.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -2.1133    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0378   -3.1315    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    2.4404   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    0.7586   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    2.0326   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2309    1.6176   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.4998   -2.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472    1.8961   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.4775   -3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043    2.5119   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1863    1.3296   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3525    2.0859    1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241    0.8834    3.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0669   -1.1974    3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -2.0540    1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416   -1.4508   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259   -2.8758   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -2.4767   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 21 12  1  0
 22  6  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₂

Average Molecular Weight

295.382

Monoisotopic Molecular Weight

295.15722892

IUPAC Name

3,4-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

Traditional Name

3,4-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(CC3N(CCC4=CC=CC=C34)C2)C=C1

InChI Identifier

InChI=1S/C19H21NO2/c1-21-18-8-7-14-11-17-15-6-4-3-5-13(15)9-10-20(17)12-16(14)19(18)22-2/h3-8,17H,9-12H2,1-2H3

InChI Key

PRDNGFIKZARQQH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Tetrahydroprotoberberine skeleton
Protoberberine skeleton
Tetrahydroisoquinoline
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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 (PMID: 31557052)

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	3.34	ALOGPS
logP	3.46	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	6.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.43 m³·mol⁻¹	ChemAxon
Polarizability	33.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	207.841	30932474
DeepCCS	[M+Na]+	183.138	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
levo-tetrahydropalmatine	COC1=C(OC)C2=C(CC3N(CCC4=CC=CC=C34)C2)C=C1	3458.2	Standard polar	33892256
levo-tetrahydropalmatine	COC1=C(OC)C2=C(CC3N(CCC4=CC=CC=C34)C2)C=C1	2392.4	Standard non polar	33892256
levo-tetrahydropalmatine	COC1=C(OC)C2=C(CC3N(CCC4=CC=CC=C34)C2)C=C1	2628.9	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 - levo-tetrahydropalmatine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-1980000000-ea6171ff36ca683282ea	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - levo-tetrahydropalmatine 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 - levo-tetrahydropalmatine 10V, Positive-QTOF	splash10-0002-0090000000-0bfd6f8a2194fcfdf538	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - levo-tetrahydropalmatine 20V, Positive-QTOF	splash10-0002-0090000000-2785a076b61fb74c279c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - levo-tetrahydropalmatine 40V, Positive-QTOF	splash10-0006-1920000000-27d87ec99d186bd5b7ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - levo-tetrahydropalmatine 10V, Negative-QTOF	splash10-0006-0090000000-84f4977e0a47a94b8f5a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - levo-tetrahydropalmatine 20V, Negative-QTOF	splash10-0006-0090000000-db5308af78f8e34a08d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - levo-tetrahydropalmatine 40V, Negative-QTOF	splash10-0006-0290000000-cbc07746a1034bac7007	2021-10-12	Wishart Lab	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

74151584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12269814

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 levo-tetrahydropalmatine (HMDB0254050)

MOL for HMDB0254050 (levo-tetrahydropalmatine)

3D MOL for HMDB0254050 (levo-tetrahydropalmatine)

3D SDF for HMDB0254050 (levo-tetrahydropalmatine)

3D-SDF for HMDB0254050 (levo-tetrahydropalmatine)

PDB for HMDB0254050 (levo-tetrahydropalmatine)

3D PDB for HMDB0254050 (levo-tetrahydropalmatine)

SMILES for HMDB0254050 (levo-tetrahydropalmatine)

INCHI for HMDB0254050 (levo-tetrahydropalmatine)

Structure for HMDB0254050 (levo-tetrahydropalmatine)

3D Structure for HMDB0254050 (levo-tetrahydropalmatine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra