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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:21:16 UTC

Update Date

2021-09-26 23:07:58 UTC

HMDB ID

HMDB0254167

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Losmapimod

Description

Losmapimod belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond. In April 2019, Fulcrum Therapeutics acquired from GSK the global rights to Losmapimod after identifying p38α/β MAPK inhibitors as potent suppressors of DUX4 expression, the de-suppression of which is theorized to cause Facioscapulohumeral muscular dystrophy (FSHD). Losmapimod is a moderately basic compound (based on its pKa). GSK investigated losmapimod as a therapeutic for major depressive disorder (MDD) on the basis of depression being correlated with elevated pro-inflammatory cytokines. However, these trials showed that losmapimod is generally well-tolerated. As of October 2019, Fulcrum is conducting two clinical trials of losmapimod for treatment of FSHD. GSK terminated development of losmapimod for COPD in 2016. GSK investigated losmapimod as a therapeutic for patients post-myocardial infarction (heart attack). Losmapimod has been shown to be potentially useful in overcoming gefitinib resistance in non-small-cell lung carcinoma. One trial, ReDUX4, is evaluating drug efficacy in a randomized controlled phase IIb clinical trial with an estimated study completion date of August 2020. Losmapimod (GW856553X) is a drug developed by GlaxoSmithKline (GSK) that selectively inhibits enzymes p38α/β mitogen-activated protein kinases (MAPKs), which are mediators of inflammation. This compound has been identified in human blood as reported by (PMID: 31557052 ). Losmapimod is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Losmapimod 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

  Mrv1652310201623472D          

 28 30  0  0  0  0            999 V2000
    3.9849    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -1.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.1743    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.0618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -4.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -0.5868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    0.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572    1.8882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    2.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    3.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967    3.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4467    3.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END

HMDB0254167
     RDKit          3D
Losmapimod
 54 56  0  0  0  0  0  0  0  0999 V2000
    1.5224    1.9707   -3.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5911    1.3772   -2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303    1.6425   -3.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327    2.3607   -4.4305 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419    1.1663   -2.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995    0.4272   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8004   -0.0652   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9853    0.0978   -0.9367 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5774   -0.7263    0.6802 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6827   -1.2219    1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5492   -0.7944    2.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4464   -2.2153    2.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3939    0.2032   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988    0.6636   -1.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    0.3617   -1.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.2374   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -0.1210   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148   -0.3618   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7864   -0.7328    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6894   -1.2306    1.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0296   -0.5535   -0.1244 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436   -0.8198    0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9370   -0.1139    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2508   -0.2938    2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572    1.3823    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3842   -0.6543    1.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -0.2384    0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8140    0.1027    0.0176 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    1.2749   -4.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    2.4031   -3.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    2.9098   -4.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9723    1.3551   -2.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6327   -0.9025    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7232   -1.0883    1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531   -0.2239    3.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4747   -0.4487    3.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2514   -2.9295    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4347   -2.6864    2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -0.3644   -0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.3726   -3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2981   -0.2033   -2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -0.1142   -1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4209   -1.9426    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -0.6678   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163    0.0254    3.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9630   -1.3308    2.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756    0.3788    2.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1987    1.9002    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8841    1.7264    1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6826    1.4663    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9916   -0.1760    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7827   -0.4271    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3598   -1.7328    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3786   -0.4246    1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  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
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 18 27  1  0
 27 28  2  0
 14  2  1  0
 28 15  1  0
 12 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
M  END

  Mrv1652310201623472D          

 28 30  0  0  0  0            999 V2000
    3.9849    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -1.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.1743    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.0618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -4.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -0.5868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    0.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572    1.8882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    2.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    3.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717    3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967    3.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4467    3.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254167

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C=C(C=C1F)C(=O)NC1CC1)C1=CC=C(C=N1)C(=O)NCC(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)

> <INCHI_KEY>
KKYABQBFGDZVNQ-UHFFFAOYSA-N

> <FORMULA>
C22H26FN3O2

> <MOLECULAR_WEIGHT>
383.467

> <EXACT_MASS>
383.200905252

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.790304033072154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-N-(2,2-dimethylpropyl)pyridine-3-carboxamide

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.6812736850000007

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.776205794023802

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.863908308253283

> <JCHEM_PKA_STRONGEST_BASIC>
2.6045795194998034

> <JCHEM_POLAR_SURFACE_AREA>
71.09

> <JCHEM_REFRACTIVITY>
107.22659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
losmapimod

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254167
     RDKit          3D
Losmapimod
 54 56  0  0  0  0  0  0  0  0999 V2000
    1.5224    1.9707   -3.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5911    1.3772   -2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303    1.6425   -3.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327    2.3607   -4.4305 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419    1.1663   -2.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995    0.4272   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8004   -0.0652   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9853    0.0978   -0.9367 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5774   -0.7263    0.6802 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6827   -1.2219    1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5492   -0.7944    2.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4464   -2.2153    2.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3939    0.2032   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988    0.6636   -1.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    0.3617   -1.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.2374   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -0.1210   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148   -0.3618   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7864   -0.7328    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6894   -1.2306    1.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0296   -0.5535   -0.1244 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436   -0.8198    0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9370   -0.1139    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2508   -0.2938    2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572    1.3823    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3842   -0.6543    1.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -0.2384    0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8140    0.1027    0.0176 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    1.2749   -4.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    2.4031   -3.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    2.9098   -4.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9723    1.3551   -2.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6327   -0.9025    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7232   -1.0883    1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531   -0.2239    3.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4747   -0.4487    3.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2514   -2.9295    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4347   -2.6864    2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -0.3644   -0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.3726   -3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2981   -0.2033   -2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -0.1142   -1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4209   -1.9426    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -0.6678   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163    0.0254    3.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9630   -1.3308    2.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756    0.3788    2.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1987    1.9002    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8841    1.7264    1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6826    1.4663    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9916   -0.1760    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7827   -0.4271    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3598   -1.7328    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3786   -0.4246    1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  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
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 18 27  1  0
 27 28  2  0
 14  2  1  0
 28 15  1  0
 12 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
M  END

HEADER    PROTEIN                                 20-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-OCT-16         0                                  
HETATM    1  C   UNK     0       7.438   1.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.438  -0.325   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.772  -1.095   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.772  -2.635   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.438  -3.405   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105  -2.635   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.105  -1.095   0.000  0.00  0.00           C+0
HETATM    8  F   UNK     0       4.771  -0.325   0.000  0.00  0.00           F+0
HETATM    9  C   UNK     0       7.438  -4.945   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.772  -5.715   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       6.105  -5.715   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.105  -7.255   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.875  -8.589   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -8.589   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.106  -0.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.106   1.215   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.439   1.985   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.773   1.215   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.773  -0.325   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      11.439  -1.095   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      14.107   1.985   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.440   1.215   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      14.107   3.525   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      15.440   4.295   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.440   5.835   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.440   7.375   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.980   5.835   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.900   5.835   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   14                                                       
CONECT   14   13   12                                                       
CONECT   15    3   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0254167
HETATM    1  C1  UNL     1       1.522   1.971  -3.778  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.591   1.377  -2.932  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.930   1.642  -3.303  1.00  0.00           C  
HETATM    4  F1  UNL     1       4.133   2.361  -4.431  1.00  0.00           F  
HETATM    5  C4  UNL     1       4.942   1.166  -2.517  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.699   0.427  -1.360  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.800  -0.065  -0.546  1.00  0.00           C  
HETATM    8  O1  UNL     1       6.985   0.098  -0.937  1.00  0.00           O  
HETATM    9  N1  UNL     1       5.577  -0.726   0.680  1.00  0.00           N  
HETATM   10  C7  UNL     1       6.683  -1.222   1.498  1.00  0.00           C  
HETATM   11  C8  UNL     1       6.549  -0.794   2.963  1.00  0.00           C  
HETATM   12  C9  UNL     1       6.446  -2.215   2.550  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.394   0.203  -1.055  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.299   0.664  -1.822  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.960   0.362  -1.333  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.184   0.237  -2.054  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.433  -0.121  -1.502  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.515  -0.362  -0.171  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.786  -0.733   0.475  1.00  0.00           C  
HETATM   20  O2  UNL     1      -2.689  -1.231   1.622  1.00  0.00           O  
HETATM   21  N2  UNL     1      -4.030  -0.553  -0.124  1.00  0.00           N  
HETATM   22  C17 UNL     1      -5.344  -0.820   0.309  1.00  0.00           C  
HETATM   23  C18 UNL     1      -5.937  -0.114   1.453  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.251  -0.294   2.761  1.00  0.00           C  
HETATM   25  C20 UNL     1      -6.157   1.382   1.150  1.00  0.00           C  
HETATM   26  C21 UNL     1      -7.384  -0.654   1.596  1.00  0.00           C  
HETATM   27  C22 UNL     1      -0.342  -0.238   0.580  1.00  0.00           C  
HETATM   28  N3  UNL     1       0.814   0.103   0.018  1.00  0.00           N  
HETATM   29  H1  UNL     1       1.272   1.275  -4.574  1.00  0.00           H  
HETATM   30  H2  UNL     1       0.716   2.403  -3.183  1.00  0.00           H  
HETATM   31  H3  UNL     1       2.012   2.910  -4.247  1.00  0.00           H  
HETATM   32  H4  UNL     1       5.972   1.355  -2.779  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.633  -0.903   1.079  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.723  -1.088   1.103  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.653  -0.224   3.277  1.00  0.00           H  
HETATM   36  H8  UNL     1       7.475  -0.449   3.491  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.251  -2.930   2.785  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.435  -2.686   2.571  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.150  -0.364  -0.171  1.00  0.00           H  
HETATM   40  H12 UNL     1      -0.183   0.373  -3.115  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.298  -0.203  -2.136  1.00  0.00           H  
HETATM   42  H14 UNL     1      -3.972  -0.114  -1.122  1.00  0.00           H  
HETATM   43  H15 UNL     1      -5.421  -1.943   0.579  1.00  0.00           H  
HETATM   44  H16 UNL     1      -6.059  -0.668  -0.569  1.00  0.00           H  
HETATM   45  H17 UNL     1      -6.016   0.025   3.544  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.963  -1.331   2.917  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.376   0.379   2.831  1.00  0.00           H  
HETATM   48  H20 UNL     1      -5.199   1.900   1.195  1.00  0.00           H  
HETATM   49  H21 UNL     1      -6.884   1.726   1.928  1.00  0.00           H  
HETATM   50  H22 UNL     1      -6.683   1.466   0.177  1.00  0.00           H  
HETATM   51  H23 UNL     1      -7.992  -0.176   0.786  1.00  0.00           H  
HETATM   52  H24 UNL     1      -7.783  -0.427   2.594  1.00  0.00           H  
HETATM   53  H25 UNL     1      -7.360  -1.733   1.410  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.379  -0.425   1.639  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3   14
CONECT    3    4    5
CONECT    5    6    6   32
CONECT    6    7   13
CONECT    7    8    8    9
CONECT    9   10   33
CONECT   10   11   12   34
CONECT   11   12   35   36
CONECT   12   37   38
CONECT   13   14   14   39
CONECT   14   15
CONECT   15   16   16   28
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   18   19   27
CONECT   19   20   20   21
CONECT   21   22   42
CONECT   22   23   43   44
CONECT   23   24   25   26
CONECT   24   45   46   47
CONECT   25   48   49   50
CONECT   26   51   52   53
CONECT   27   28   28   54
END

HMDB0254167
     RDKit          3D
Losmapimod
 54 56  0  0  0  0  0  0  0  0999 V2000
    1.5224    1.9707   -3.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5911    1.3772   -2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303    1.6425   -3.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327    2.3607   -4.4305 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419    1.1663   -2.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995    0.4272   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8004   -0.0652   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9853    0.0978   -0.9367 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5774   -0.7263    0.6802 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6827   -1.2219    1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5492   -0.7944    2.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4464   -2.2153    2.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3939    0.2032   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988    0.6636   -1.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    0.3617   -1.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841    0.2374   -2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -0.1210   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148   -0.3618   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7864   -0.7328    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6894   -1.2306    1.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0296   -0.5535   -0.1244 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436   -0.8198    0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9370   -0.1139    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2508   -0.2938    2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572    1.3823    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3842   -0.6543    1.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -0.2384    0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8140    0.1027    0.0176 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    1.2749   -4.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    2.4031   -3.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    2.9098   -4.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9723    1.3551   -2.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6327   -0.9025    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7232   -1.0883    1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531   -0.2239    3.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4747   -0.4487    3.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2514   -2.9295    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4347   -2.6864    2.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -0.3644   -0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.3726   -3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2981   -0.2033   -2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -0.1142   -1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4209   -1.9426    0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -0.6678   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0163    0.0254    3.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9630   -1.3308    2.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756    0.3788    2.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1987    1.9002    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8841    1.7264    1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6826    1.4663    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9916   -0.1760    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7827   -0.4271    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3598   -1.7328    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3786   -0.4246    1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  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
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 18 27  1  0
 27 28  2  0
 14  2  1  0
 28 15  1  0
 12 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
GW-856553GSK-AHAB	ChEMBL
GW856553X	ChEMBL
GSK-AHAB	MeSH
6-(5-((cyclopropylamino)Carbonyl)-3-fluoro-2-methylphenyl)-N-(2,2-dimethylprpyl)-3-pyridinecarboxamide	MeSH

Chemical Formula

C₂₂H₂₆FN₃O₂

Average Molecular Weight

383.467

Monoisotopic Molecular Weight

383.200905252

IUPAC Name

6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-N-(2,2-dimethylpropyl)pyridine-3-carboxamide

Traditional Name

losmapimod

CAS Registry Number

Not Available

SMILES

CC1=C(C=C(C=C1F)C(=O)NC1CC1)C1=CC=C(C=N1)C(=O)NCC(C)(C)C

InChI Identifier

InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)

InChI Key

KKYABQBFGDZVNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

Alternative Parents

Substituents

2-phenylpyridine
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Nicotinamide
Pyridinecarboxamide
Pyridine carboxylic acid or derivatives
Benzamide
Benzoic acid or derivatives
Toluamide
P-toluamide
Benzoyl
Toluene
Halobenzene
Fluorobenzene
Aryl halide
Benzenoid
Aryl fluoride
Monocyclic benzene moiety
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organofluoride
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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: HMDB0254167)

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	3.5	ALOGPS
logP	3.68	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.23 m³·mol⁻¹	ChemAxon
Polarizability	42.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	200.027	30932474
DeepCCS	[M-H]-	197.669	30932474
DeepCCS	[M-2H]-	232.002	30932474
DeepCCS	[M+Na]+	207.02	30932474
AllCCS	[M+H]+	193.9	32859911
AllCCS	[M+H-H2O]+	191.3	32859911
AllCCS	[M+NH4]+	196.3	32859911
AllCCS	[M+Na]+	196.9	32859911
AllCCS	[M-H]-	196.1	32859911
AllCCS	[M+Na-2H]-	196.5	32859911
AllCCS	[M+HCOO]-	197.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Losmapimod	CC1=C(C=C(C=C1F)C(=O)NC1CC1)C1=CC=C(C=N1)C(=O)NCC(C)(C)C	4224.0	Standard polar	33892256
Losmapimod	CC1=C(C=C(C=C1F)C(=O)NC1CC1)C1=CC=C(C=N1)C(=O)NCC(C)(C)C	3335.2	Standard non polar	33892256
Losmapimod	CC1=C(C=C(C=C1F)C(=O)NC1CC1)C1=CC=C(C=N1)C(=O)NCC(C)(C)C	3395.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Losmapimod,1TMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1	3166.5	Semi standard non polar	33892256
Losmapimod,1TMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1	3192.1	Standard non polar	33892256
Losmapimod,1TMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1	3701.5	Standard polar	33892256
Losmapimod,1TMS,isomer #2	CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C)C=N1	3158.9	Semi standard non polar	33892256
Losmapimod,1TMS,isomer #2	CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C)C=N1	3099.5	Standard non polar	33892256
Losmapimod,1TMS,isomer #2	CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C)C=N1	3561.5	Standard polar	33892256
Losmapimod,2TMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C)C=N1	3037.6	Semi standard non polar	33892256
Losmapimod,2TMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C)C=N1	3168.9	Standard non polar	33892256
Losmapimod,2TMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C)C=N1	3429.2	Standard polar	33892256
Losmapimod,1TBDMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C(C)(C)C)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1	3422.5	Semi standard non polar	33892256
Losmapimod,1TBDMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C(C)(C)C)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1	3394.2	Standard non polar	33892256
Losmapimod,1TBDMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C(C)(C)C)C=C1C1=CC=C(C(=O)NCC(C)(C)C)C=N1	3735.8	Standard polar	33892256
Losmapimod,1TBDMS,isomer #2	CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C(C)(C)C)C=N1	3409.6	Semi standard non polar	33892256
Losmapimod,1TBDMS,isomer #2	CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C(C)(C)C)C=N1	3306.0	Standard non polar	33892256
Losmapimod,1TBDMS,isomer #2	CC1=C(F)C=C(C(=O)NC2CC2)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C(C)(C)C)C=N1	3630.9	Standard polar	33892256
Losmapimod,2TBDMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C(C)(C)C)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C(C)(C)C)C=N1	3501.7	Semi standard non polar	33892256
Losmapimod,2TBDMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C(C)(C)C)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C(C)(C)C)C=N1	3584.5	Standard non polar	33892256
Losmapimod,2TBDMS,isomer #1	CC1=C(F)C=C(C(=O)N(C2CC2)[Si](C)(C)C(C)(C)C)C=C1C1=CC=C(C(=O)N(CC(C)(C)C)[Si](C)(C)C(C)(C)C)C=N1	3576.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Losmapimod GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-7097000000-68d103fb466805f14830	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Losmapimod 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 - Losmapimod 10V, Positive-QTOF	splash10-001i-6019000000-4cf4a70c693798233aa4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 20V, Positive-QTOF	splash10-000l-9054000000-7c0b9a869c1771e8de43	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 40V, Positive-QTOF	splash10-03di-9170000000-35036dfc63c6b35cca1f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 10V, Negative-QTOF	splash10-001i-0009000000-d9bf93d5f3d18dea80e6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 20V, Negative-QTOF	splash10-001i-3339000000-b70912b192b36b9f706f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 40V, Negative-QTOF	splash10-01rl-9330000000-51513a16ae7f0c370f3b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 10V, Positive-QTOF	splash10-001i-0009000000-7d7e179b280b62ddf208	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 20V, Positive-QTOF	splash10-001i-2019000000-6737ed83b0812e94591a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 40V, Positive-QTOF	splash10-01ox-1191000000-9dfd53d50dab0d2f2d2f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 10V, Negative-QTOF	splash10-001i-0009000000-48c65ae05cb08bc2fd9d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 20V, Negative-QTOF	splash10-001i-2039000000-1f0a10f8c1e6959a2784	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losmapimod 40V, Negative-QTOF	splash10-0006-8193000000-cdebde1322690dbd3b34	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

DB12270

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

Losmapimod

METLIN ID

Not Available

PubChem Compound

11552706

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 Losmapimod (HMDB0254167)

MOL for HMDB0254167 (Losmapimod)

3D MOL for HMDB0254167 (Losmapimod)

3D SDF for HMDB0254167 (Losmapimod)

3D-SDF for HMDB0254167 (Losmapimod)

PDB for HMDB0254167 (Losmapimod)

3D PDB for HMDB0254167 (Losmapimod)

SMILES for HMDB0254167 (Losmapimod)

INCHI for HMDB0254167 (Losmapimod)

Structure for HMDB0254167 (Losmapimod)

3D Structure for HMDB0254167 (Losmapimod)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra