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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:11:08 UTC

Update Date

2021-09-26 23:07:48 UTC

HMDB ID

HMDB0254060

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Levoprotiline

Description

Levoprotiline, also known as C 49802b-ba or hydroxymaprotilin, belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. Based on a literature review a significant number of articles have been published on Levoprotiline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Levoprotiline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Levoprotiline 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

HMDB0254060
     RDKit          3D
Levoprotiline
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.6234    0.8845   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -0.0530    0.0394 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399   -0.7565   -0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9222   -1.6925   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7019   -2.5838    0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804   -1.1344    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.1850    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.1190   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6775    2.1726   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301    1.6021   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041    1.1486    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878    1.6066    2.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353    1.0811    3.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4563    0.1500    3.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6711   -0.2929    2.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212    0.2226    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023    0.3195   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661    0.0968   -1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -1.1439   -2.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -2.1078   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3178   -1.8612   -1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -0.6520   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7634    0.6999   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    1.9461   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144    0.8789   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    0.4177    0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -0.1521   -1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964   -1.4814   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031   -2.3527   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -1.9974    0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -1.9760    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.6430    1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    0.8383   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207    1.5560   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5055    3.0013    0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    2.6738   -1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495    2.2939   -0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    2.3346    1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0711    1.4555    4.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030   -0.2235    4.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -1.0204    2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9960    0.8752   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844   -1.3632   -3.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.0934   -2.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5883   -2.6084   -1.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  7  1  0
 22 17  1  0
 22  7  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END

  Mrv1652309112115112D          

 22 25  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.8579    0.8250    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
    2.9954   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -1.1000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    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
    0.7145   -1.2375    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
    1.4289    0.0000    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
    4.2868    0.8250    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  1  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  1  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  6 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
 16 21  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254060

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC(O)CC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO/c1-21-13-14(22)12-20-11-10-15(16-6-2-4-8-18(16)20)17-7-3-5-9-19(17)20/h2-9,14-15,21-22H,10-13H2,1H3

> <INCHI_KEY>
FDXQKWSTUZCCTM-UHFFFAOYSA-N

> <FORMULA>
C20H23NO

> <MOLECULAR_WEIGHT>
293.41

> <EXACT_MASS>
293.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.17877997260398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(methylamino)-3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propan-2-ol

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.297201167333334

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.857072033674143

> <JCHEM_PKA_STRONGEST_BASIC>
9.91818198156226

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
100.6632

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(methylamino)-3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254060
     RDKit          3D
Levoprotiline
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.6234    0.8845   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -0.0530    0.0394 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399   -0.7565   -0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9222   -1.6925   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7019   -2.5838    0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804   -1.1344    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.1850    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.1190   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6775    2.1726   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301    1.6021   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041    1.1486    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878    1.6066    2.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353    1.0811    3.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4563    0.1500    3.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6711   -0.2929    2.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212    0.2226    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023    0.3195   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661    0.0968   -1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -1.1439   -2.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -2.1078   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3178   -1.8612   -1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -0.6520   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7634    0.6999   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    1.9461   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144    0.8789   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    0.4177    0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -0.1521   -1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964   -1.4814   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031   -2.3527   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -1.9974    0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -1.9760    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.6430    1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    0.8383   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207    1.5560   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5055    3.0013    0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    2.6738   -1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495    2.2939   -0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    2.3346    1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0711    1.4555    4.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030   -0.2235    4.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -1.0204    2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9960    0.8752   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844   -1.3632   -3.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.0934   -2.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5883   -2.6084   -1.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  7  1  0
 22 17  1  0
 22  7  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       8.002   4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.591  -1.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.591  -2.053   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15   21                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10    6                                                  
CONECT   16    9   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    6   16                                                  
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0254060
HETATM    1  C1  UNL     1       4.623   0.885  -0.536  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.700  -0.053   0.039  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.940  -0.757  -0.948  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.922  -1.692  -0.350  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.702  -2.584   0.452  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.880  -1.134   0.502  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.135  -0.185   0.077  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.382   1.119  -0.529  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.677   2.173  -0.655  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.030   1.602  -0.328  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.904   1.149   1.109  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.688   1.607   2.124  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.435   1.081   3.387  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.456   0.150   3.630  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.671  -0.293   2.546  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.921   0.223   1.316  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.202   0.320  -1.080  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.266   0.097  -1.901  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.351  -1.144  -2.498  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.405  -2.108  -2.272  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.318  -1.861  -1.425  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.215  -0.652  -0.832  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.763   0.700  -1.626  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.239   1.946  -0.483  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.614   0.879  -0.060  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.102   0.418   0.719  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.616  -0.152  -1.784  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.696  -1.481  -1.441  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.603  -2.353  -1.194  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.348  -1.997   0.919  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.328  -1.976   1.052  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.429  -0.643   1.386  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.603   0.838  -1.606  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.221   1.556  -0.000  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.505   3.001   0.093  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.695   2.674  -1.654  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.849   2.294  -0.473  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.448   2.335   1.912  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.071   1.455   4.196  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.303  -0.223   4.623  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.078  -1.020   2.787  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.996   0.875  -2.060  1.00  0.00           H  
HETATM   43  H21 UNL     1      -4.184  -1.363  -3.161  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.474  -3.093  -2.746  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.588  -2.608  -1.225  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26
CONECT    3    4   27   28
CONECT    4    5    6   29
CONECT    5   30
CONECT    6    7   31   32
CONECT    7    8   16   22
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   17   37
CONECT   11   12   12   16
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15   40
CONECT   15   16   16   41
CONECT   17   18   18   22
CONECT   18   19   42
CONECT   19   20   20   43
CONECT   20   21   44
CONECT   21   22   22   45
END

HMDB0254060
     RDKit          3D
Levoprotiline
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.6234    0.8845   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -0.0530    0.0394 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399   -0.7565   -0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9222   -1.6925   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7019   -2.5838    0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804   -1.1344    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.1850    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.1190   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6775    2.1726   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301    1.6021   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041    1.1486    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878    1.6066    2.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353    1.0811    3.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4563    0.1500    3.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6711   -0.2929    2.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9212    0.2226    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023    0.3195   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2661    0.0968   -1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507   -1.1439   -2.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -2.1078   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3178   -1.8612   -1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -0.6520   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7634    0.6999   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    1.9461   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144    0.8789   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    0.4177    0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -0.1521   -1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964   -1.4814   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031   -2.3527   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -1.9974    0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -1.9760    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.6430    1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    0.8383   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207    1.5560   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5055    3.0013    0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    2.6738   -1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495    2.2939   -0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4482    2.3346    1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0711    1.4555    4.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030   -0.2235    4.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -1.0204    2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9960    0.8752   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844   -1.3632   -3.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -3.0934   -2.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5883   -2.6084   -1.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  7  1  0
 22 17  1  0
 22  7  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
C 49802b-Ba	HMDB
C-49802b-Ba	HMDB
Hydroxymaprotilin	HMDB
Hydroxymaprotilin hydrochloride	HMDB
Hydroxymaprotilin hydrochloride, (R)-isomer	HMDB
Hydroxymaprotilin hydrochloride, (S)-isomer	HMDB
Hydroxymaprotilin, (+-)-isomer	HMDB
Hydroxymaprotilin, (+r)-isomer	HMDB
Hydroxymaprotilin, (S)-isomer	HMDB
Levoprotiline	MeSH

Chemical Formula

C₂₀H₂₃NO

Average Molecular Weight

293.41

Monoisotopic Molecular Weight

293.177964365

IUPAC Name

1-(methylamino)-3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propan-2-ol

Traditional Name

1-(methylamino)-3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propan-2-ol

CAS Registry Number

Not Available

SMILES

CNCC(O)CC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

InChI Identifier

InChI=1S/C20H23NO/c1-21-13-14(22)12-20-11-10-15(16-6-2-4-8-18(16)20)17-7-3-5-9-19(17)20/h2-9,14-15,21-22H,10-13H2,1H3

InChI Key

FDXQKWSTUZCCTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Tetralin
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.56	ALOGPS
logP	3.3	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	9.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.66 m³·mol⁻¹	ChemAxon
Polarizability	34.18 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]-	205.18	30932474
DeepCCS	[M+Na]+	180.745	30932474
AllCCS	[M+H]+	172.5	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	175.4	32859911
AllCCS	[M+Na]+	176.3	32859911
AllCCS	[M-H]-	177.3	32859911
AllCCS	[M+Na-2H]-	176.9	32859911
AllCCS	[M+HCOO]-	176.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levoprotiline	CNCC(O)CC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	3175.4	Standard polar	33892256
Levoprotiline	CNCC(O)CC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	2493.2	Standard non polar	33892256
Levoprotiline	CNCC(O)CC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	2399.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levoprotiline,2TMS,isomer #1	CN(CC(CC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C	2777.6	Semi standard non polar	33892256
Levoprotiline,2TMS,isomer #1	CN(CC(CC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C	2818.8	Standard non polar	33892256
Levoprotiline,2TMS,isomer #1	CN(CC(CC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)O[Si](C)(C)C)[Si](C)(C)C	2801.3	Standard polar	33892256
Levoprotiline,2TBDMS,isomer #1	CN(CC(CC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3263.8	Semi standard non polar	33892256
Levoprotiline,2TBDMS,isomer #1	CN(CC(CC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3347.4	Standard non polar	33892256
Levoprotiline,2TBDMS,isomer #1	CN(CC(CC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2989.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Levoprotiline GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9050000000-4f043c6944fef6ddac9d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levoprotiline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levoprotiline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levoprotiline GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levoprotiline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levoprotiline GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Levoprotiline 10V, Positive-QTOF	splash10-0006-0090000000-e12e1d3f981045dbeaeb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoprotiline 20V, Positive-QTOF	splash10-0006-2090000000-2b05288321ef0b9c1ec9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoprotiline 40V, Positive-QTOF	splash10-0a4l-6090000000-8a9654ecb4b009dbf166	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoprotiline 10V, Negative-QTOF	splash10-0006-0090000000-17a2775e8d18d2b59e53	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoprotiline 20V, Negative-QTOF	splash10-0006-0090000000-5ef4c346df1bc66f41f8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levoprotiline 40V, Negative-QTOF	splash10-0zfr-0090000000-bc4922658119727f0411	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

35026

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxaprotiline

METLIN ID

Not Available

PubChem Compound

38207

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 Levoprotiline (HMDB0254060)

MOL for HMDB0254060 (Levoprotiline)

3D MOL for HMDB0254060 (Levoprotiline)

3D SDF for HMDB0254060 (Levoprotiline)

3D-SDF for HMDB0254060 (Levoprotiline)

PDB for HMDB0254060 (Levoprotiline)

3D PDB for HMDB0254060 (Levoprotiline)

SMILES for HMDB0254060 (Levoprotiline)

INCHI for HMDB0254060 (Levoprotiline)

Structure for HMDB0254060 (Levoprotiline)

3D Structure for HMDB0254060 (Levoprotiline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra