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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:23:22 UTC

Update Date

2021-09-26 23:09:20 UTC

HMDB ID

HMDB0254907

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Moxaverine

Description

Moxaverine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Moxaverine is a very strong basic compound (based on its pKa). The ocular efficacy of moxaverine has been explored in the clinic. Moxaverine has been used in therapy based on the direct vasodilatory effect of the drug, a phosphodiesterase inhibitor, and on its influence on the rheological properties of red blood cells. Moxaverine hydrochloride (Kollateral forte®, Ursapharm. Saarbrücken, Germany) has been shown to increase ocular blood flow in patients with age-related macular degeneration, primary open angle glaucoma, and to increase choroidal and retrobulbar blood flow in elderly patients with eye diseases associated with hypo-perfusion. This compound has been identified in human blood as reported by (PMID: 31557052 ). Moxaverine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Moxaverine 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

HMDB0254907
     RDKit          3D
Moxaverine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.1907    4.4685   -1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    4.1455   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778    2.7052   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736    1.7966   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.4764   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099   -0.4130   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -1.7514   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435   -2.6808   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241   -2.2747   -0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977   -2.1475    0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1536   -3.4711    0.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313   -3.8778    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.2257    0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    0.0991    0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5826    1.0040    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    0.6260    1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720    0.0679    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151    0.8287   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893    0.2817   -1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8843   -1.0369   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -1.8089   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635   -1.2374    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3289    2.2942    0.4004 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    4.1988   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937    5.5932   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    4.0990   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157    4.7374    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0772    4.4089   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6917    2.1167   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5152   -0.0951   -0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445   -3.1249   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489   -1.6019   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3490   -1.7023   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671   -3.6354    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -3.2807    2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0563   -4.9724    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615   -1.5844    1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -0.0478    2.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999    1.5544    1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2384    1.8491   -0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9984    0.8816   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6463   -1.4857   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -2.8428   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -1.9344    1.3292 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  2  0
 23  3  1  0
 14  5  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

  Mrv1572004221606522D          

 23 25  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16  4  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  2  0  0  0  0
 19 12  2  0  0  0  0
 20 13  2  0  0  0  0
 20 19  1  0  0  0  0
 21 16  2  0  0  0  0
 21 18  1  0  0  0  0
 22  2  1  0  0  0  0
 22 19  1  0  0  0  0
 23  3  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254907

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=NC(CC2=CC=CC=C2)=C2C=C(OC)C(OC)=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO2/c1-4-16-11-15-12-19(22-2)20(23-3)13-17(15)18(21-16)10-14-8-6-5-7-9-14/h5-9,11-13H,4,10H2,1-3H3

> <INCHI_KEY>
MYCMTMIGRXJNSO-UHFFFAOYSA-N

> <FORMULA>
C20H21NO2

> <MOLECULAR_WEIGHT>
307.393

> <EXACT_MASS>
307.15722892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.01797798744707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-benzyl-3-ethyl-6,7-dimethoxyisoquinoline

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
4.227323619

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.489882525472209

> <JCHEM_POLAR_SURFACE_AREA>
31.35

> <JCHEM_REFRACTIVITY>
91.80949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kollateral

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254907
     RDKit          3D
Moxaverine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.1907    4.4685   -1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    4.1455   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778    2.7052   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736    1.7966   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.4764   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099   -0.4130   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -1.7514   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435   -2.6808   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241   -2.2747   -0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977   -2.1475    0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1536   -3.4711    0.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313   -3.8778    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.2257    0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    0.0991    0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5826    1.0040    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    0.6260    1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720    0.0679    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151    0.8287   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893    0.2817   -1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8843   -1.0369   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -1.8089   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635   -1.2374    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3289    2.2942    0.4004 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    4.1988   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937    5.5932   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    4.0990   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157    4.7374    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0772    4.4089   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6917    2.1167   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5152   -0.0951   -0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445   -3.1249   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489   -1.6019   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3490   -1.7023   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671   -3.6354    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -3.2807    2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0563   -4.9724    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615   -1.5844    1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -0.0478    2.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999    1.5544    1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2384    1.8491   -0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9984    0.8816   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6463   -1.4857   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -2.8428   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -1.9344    1.3292 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  2  0
 23  3  1  0
 14  5  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    1   16                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   14   18                                                       
CONECT   11   15   16                                                       
CONECT   12   15   19                                                       
CONECT   13   17   20                                                       
CONECT   14    8    9   10                                                  
CONECT   15   11   12   17                                                  
CONECT   16    4   11   21                                                  
CONECT   17   13   15   18                                                  
CONECT   18   10   17   21                                                  
CONECT   19   12   20   22                                                  
CONECT   20   13   19   23                                                  
CONECT   21   16   18                                                       
CONECT   22    2   19                                                       
CONECT   23    3   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0254907
HETATM    1  C1  UNL     1      -2.191   4.468  -1.220  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.899   4.146  -0.554  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.778   2.705  -0.196  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.774   1.797  -0.465  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.596   0.476  -0.107  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.610  -0.413  -0.374  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.453  -1.751  -0.005  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.444  -2.681  -0.253  1.00  0.00           O  
HETATM    9  C8  UNL     1      -4.624  -2.275  -0.884  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.298  -2.147   0.614  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.154  -3.471   0.975  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.031  -3.878   1.609  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.317  -1.226   0.859  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.404   0.099   0.522  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.583   1.004   0.787  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.853   0.626   1.399  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.872   0.068   0.508  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.515   0.829  -0.457  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.489   0.282  -1.257  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.884  -1.037  -1.154  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.255  -1.809  -0.200  1.00  0.00           C  
HETATM   22  C20 UNL     1       3.263  -1.237   0.610  1.00  0.00           C  
HETATM   23  N1  UNL     1       0.329   2.294   0.400  1.00  0.00           N  
HETATM   24  H1  UNL     1      -2.202   4.199  -2.306  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.294   5.593  -1.208  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.086   4.099  -0.682  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.816   4.737   0.380  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.077   4.409  -1.248  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.692   2.117  -0.957  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.515  -0.095  -0.860  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.244  -3.125  -1.236  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.249  -1.602  -0.261  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.349  -1.702  -1.794  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.867  -3.635   0.889  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.236  -3.281   2.510  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.056  -4.972   1.797  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.561  -1.584   1.362  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.685  -0.048   2.286  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.300   1.554   1.858  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.238   1.849  -0.566  1.00  0.00           H  
HETATM   41  H18 UNL     1       4.998   0.882  -2.020  1.00  0.00           H  
HETATM   42  H19 UNL     1       5.646  -1.486  -1.772  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.549  -2.843  -0.102  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.850  -1.934   1.329  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    4   23
CONECT    4    5   29
CONECT    5    6    6   14
CONECT    6    7   30
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   31   32   33
CONECT   10   11   13
CONECT   11   12
CONECT   12   34   35   36
CONECT   13   14   14   37
CONECT   14   15
CONECT   15   16   23   23
CONECT   16   17   38   39
CONECT   17   18   18   22
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   21   42
CONECT   21   22   22   43
CONECT   22   44
END

HMDB0254907
     RDKit          3D
Moxaverine
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.1907    4.4685   -1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    4.1455   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778    2.7052   -0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736    1.7966   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.4764   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099   -0.4130   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -1.7514   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435   -2.6808   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241   -2.2747   -0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977   -2.1475    0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1536   -3.4711    0.9749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313   -3.8778    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.2257    0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    0.0991    0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5826    1.0040    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529    0.6260    1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720    0.0679    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151    0.8287   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893    0.2817   -1.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8843   -1.0369   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -1.8089   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635   -1.2374    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3289    2.2942    0.4004 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    4.1988   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937    5.5932   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    4.0990   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157    4.7374    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0772    4.4089   -1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6917    2.1167   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5152   -0.0951   -0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445   -3.1249   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489   -1.6019   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3490   -1.7023   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671   -3.6354    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357   -3.2807    2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0563   -4.9724    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615   -1.5844    1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -0.0478    2.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999    1.5544    1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2384    1.8491   -0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9984    0.8816   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6463   -1.4857   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -2.8428   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -1.9344    1.3292 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  2  0
 23  3  1  0
 14  5  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Certonal	MeSH
Moxaverine	MeSH
Eupaverin	MeSH
Kollateral	MeSH
Moxaverine hydrochloride	MeSH
Moxaverine sulfate (1:1)	MeSH

Chemical Formula

C₂₀H₂₁NO₂

Average Molecular Weight

307.393

Monoisotopic Molecular Weight

307.15722892

IUPAC Name

1-benzyl-3-ethyl-6,7-dimethoxyisoquinoline

Traditional Name

kollateral

CAS Registry Number

Not Available

SMILES

CCC1=NC(CC2=CC=CC=C2)=C2C=C(OC)C(OC)=CC2=C1

InChI Identifier

InChI=1S/C20H21NO2/c1-4-16-11-15-12-19(22-2)20(23-3)13-17(15)18(21-16)10-14-8-6-5-7-9-14/h5-9,11-13H,4,10H2,1-3H3

InChI Key

MYCMTMIGRXJNSO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
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: HMDB0254907)

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	5.01	ALOGPS
logP	4.23	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	6.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	31.35 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.81 m³·mol⁻¹	ChemAxon
Polarizability	35.02 Å³	ChemAxon
Number of Rings	3	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+H]+	174.225	30932474
DeepCCS	[M-H]-	171.867	30932474
DeepCCS	[M-2H]-	205.401	30932474
DeepCCS	[M+Na]+	180.628	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.3	32859911
AllCCS	[M+NH4]+	178.2	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	179.7	32859911
AllCCS	[M+HCOO]-	179.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Moxaverine	CCC1=NC(CC2=CC=CC=C2)=C2C=C(OC)C(OC)=CC2=C1	3413.3	Standard polar	33892256
Moxaverine	CCC1=NC(CC2=CC=CC=C2)=C2C=C(OC)C(OC)=CC2=C1	2561.7	Standard non polar	33892256
Moxaverine	CCC1=NC(CC2=CC=CC=C2)=C2C=C(OC)C(OC)=CC2=C1	2576.5	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 - Moxaverine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1090000000-c1f60b07a710b1c88504	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Moxaverine 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 - Moxaverine 10V, Positive-QTOF	splash10-0a4i-1019000000-ce01eb1d580dd73e2998	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 20V, Positive-QTOF	splash10-052f-9075000000-c77d1896f7055ddd88da	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 40V, Positive-QTOF	splash10-0006-9120000000-51fbbdc93c9dc63406e8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 10V, Negative-QTOF	splash10-0a4i-0009000000-5465bf88fa4e1d47f453	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 20V, Negative-QTOF	splash10-0a4i-0089000000-779caa99d8c70d4d3bfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 40V, Negative-QTOF	splash10-0nou-2390000000-b7827a10f429306840a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 10V, Positive-QTOF	splash10-0a4i-0009000000-6ceb6b9c3bd890497668	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 20V, Positive-QTOF	splash10-0a4i-2019000000-717451335b0d0195a1d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 40V, Positive-QTOF	splash10-0006-9471000000-de71e436a4e59bb81eb4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 10V, Negative-QTOF	splash10-0a4i-0009000000-c05956f8e1d07e103bee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 20V, Negative-QTOF	splash10-0a4i-0039000000-2f2e7de4fda02a381721	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Moxaverine 40V, Negative-QTOF	splash10-0w2c-3294000000-1d79442fc60fbd2a2741	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

DB12251

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Moxaverine

METLIN ID

Not Available

PubChem Compound

70882

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 Moxaverine (HMDB0254907)

MOL for HMDB0254907 (Moxaverine)

3D MOL for HMDB0254907 (Moxaverine)

3D SDF for HMDB0254907 (Moxaverine)

3D-SDF for HMDB0254907 (Moxaverine)

PDB for HMDB0254907 (Moxaverine)

3D PDB for HMDB0254907 (Moxaverine)

SMILES for HMDB0254907 (Moxaverine)

INCHI for HMDB0254907 (Moxaverine)

Structure for HMDB0254907 (Moxaverine)

3D Structure for HMDB0254907 (Moxaverine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra