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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:15:08 UTC

Update Date

2021-09-26 23:07:53 UTC

HMDB ID

HMDB0254104

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Linopirdine

Description

Linopirdine, also known as dup-996, belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The acid chloride then cyclizes into the ring on heating to afford (3). Alkylation with α-chloropicoline proceeds with hydroxide as the base to afford Linopirdine (6). The 3 position is now activated by the adjacent benzene ring on one side and the carbonyl group on the other. Linopirdine is a putative cognition-enhancing drug with a novel mechanism of action. Linopirdine is a very strong basic compound (based on its pKa). The synthesis starts with a standard scheme for preparing indoxyls. In a murine model linopirdine is able to nearly completely reverse the senescence-related decline in cortical c-FOS, an effect which is blocked by atropine and MK-801, suggesting Linopirdine can compensate for the age related decline in acetylcholine release. Linopirdine blocks the KCNQ2\3 heteromer M current with an IC50 of 2.4 micromolar disinhibiting acetylcholine release, and increasing hippocampal CA3-schaffer collateral mediated glutamate release onto CA1 pyramidal neurons. Reaction of that product with 4-picoline under phase-transfer conditions catalyzed by a quaternary salt affords the carbinol (4) from addition of the transient anion on the methyl group of the picoline to the more electrophilic carbonyl group. The alcohol is then dehydrated by means of acetic anhydride and the resulting olefin hydrogenated to afford the indolone (5). Linopirdine also blocks homomeric KCNQ1 and KCNQ4 voltage gated potassium channels which contribute to vascular tone with substantially less selectivity than KCNQ2/3. Thus, acylation of diphenylamine with oxalyl chloride leads to the amide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Linopirdine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Linopirdine 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

  Mrv1572004221604392D          

 30 34  0  0  0  0            999 V2000
    0.5121    4.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400    4.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191    4.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    1.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    2.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    3.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5740    3.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760    0.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760    2.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -0.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920   -0.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -1.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5379    0.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469   -0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121   -1.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1168   -0.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    0.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220    3.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    1.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    2.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920    1.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    1.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242   -0.8010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    2.3610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0330    1.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 20 10  2  0  0  0  0
 20 11  1  0  0  0  0
 20 18  1  0  0  0  0
 21 12  2  0  0  0  0
 21 13  1  0  0  0  0
 21 19  1  0  0  0  0
 22  6  2  0  0  0  0
 22  7  1  0  0  0  0
 23  8  2  0  0  0  0
 24  9  2  0  0  0  0
 24 23  1  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 14  2  0  0  0  0
 27 15  1  0  0  0  0
 28 16  2  0  0  0  0
 28 17  1  0  0  0  0
 29 22  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 25  2  0  0  0  0
M  END

HMDB0254104
     RDKit          3D
Linopirdine
 51 55  0  0  0  0  0  0  0  0999 V2000
    0.6033    1.6030   -1.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6668    0.6453   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631    0.1322    0.0483 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996    0.5002   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000    1.5225    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121    1.9026    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8135    1.2209   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2392    0.1891   -1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.1664   -1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4845   -0.9094    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2897   -1.7266    1.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -2.6672    2.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -2.8125    2.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -2.0012    1.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334   -1.0526    1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -0.0685    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147    0.9014    0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7987    2.1382    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590    2.2500   -0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5517    3.4326   -0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493    4.5085   -0.8421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    4.4621   -0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    3.2981    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -0.8052   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816   -1.6356   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -2.9795   -0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4362   -3.7482   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5901   -3.2303   -0.9843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -1.9690   -1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5152   -1.1718   -1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    2.0766    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6133    2.7047    0.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8291    1.4824   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095   -0.3268   -2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983   -0.9799   -1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -1.6272    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -3.2984    3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -3.5384    3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651   -2.1498    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    0.4512    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    1.2112    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7665    1.4343   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5448    3.4885   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006    5.3678   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    3.3178    0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -0.0286   -1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261   -1.3590   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3989   -3.4580   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072   -4.7765   -0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6234   -1.5837   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6849   -0.1709   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 16  2  1  0
 23 18  1  0
 30 25  1  0
  9  4  1  0
 15 10  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 26 48  1  0
 27 49  1  0
 29 50  1  0
 30 51  1  0
M  END

  Mrv1572004221604392D          

 30 34  0  0  0  0            999 V2000
    0.5121    4.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400    4.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191    4.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    1.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    2.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    3.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5740    3.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760    0.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760    2.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -0.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920   -0.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -1.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5379    0.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469   -0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121   -1.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1168   -0.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2150    0.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220    3.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    1.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    2.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920    1.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    1.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242   -0.8010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    2.3610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0330    1.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 20 10  2  0  0  0  0
 20 11  1  0  0  0  0
 20 18  1  0  0  0  0
 21 12  2  0  0  0  0
 21 13  1  0  0  0  0
 21 19  1  0  0  0  0
 22  6  2  0  0  0  0
 22  7  1  0  0  0  0
 23  8  2  0  0  0  0
 24  9  2  0  0  0  0
 24 23  1  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 14  2  0  0  0  0
 27 15  1  0  0  0  0
 28 16  2  0  0  0  0
 28 17  1  0  0  0  0
 29 22  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254104

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1N(C2=CC=CC=C2C1(CC1=CC=NC=C1)CC1=CC=NC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H21N3O/c30-25-26(18-20-10-14-27-15-11-20,19-21-12-16-28-17-13-21)23-8-4-5-9-24(23)29(25)22-6-2-1-3-7-22/h1-17H,18-19H2

> <INCHI_KEY>
YEJCDKJIEMIWRQ-UHFFFAOYSA-N

> <FORMULA>
C26H21N3O

> <MOLECULAR_WEIGHT>
391.474

> <EXACT_MASS>
391.168462308

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.75592565013212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-phenyl-3,3-bis[(pyridin-4-yl)methyl]-2,3-dihydro-1H-indol-2-one

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
4.414475706000001

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.351237843379331

> <JCHEM_POLAR_SURFACE_AREA>
46.09

> <JCHEM_REFRACTIVITY>
116.63209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linopirdine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254104
     RDKit          3D
Linopirdine
 51 55  0  0  0  0  0  0  0  0999 V2000
    0.6033    1.6030   -1.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6668    0.6453   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631    0.1322    0.0483 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996    0.5002   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000    1.5225    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121    1.9026    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8135    1.2209   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2392    0.1891   -1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.1664   -1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4845   -0.9094    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2897   -1.7266    1.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -2.6672    2.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -2.8125    2.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -2.0012    1.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334   -1.0526    1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -0.0685    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147    0.9014    0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7987    2.1382    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590    2.2500   -0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5517    3.4326   -0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493    4.5085   -0.8421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    4.4621   -0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    3.2981    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -0.8052   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816   -1.6356   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -2.9795   -0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4362   -3.7482   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5901   -3.2303   -0.9843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -1.9690   -1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5152   -1.1718   -1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    2.0766    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6133    2.7047    0.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8291    1.4824   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095   -0.3268   -2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983   -0.9799   -1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -1.6272    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -3.2984    3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -3.5384    3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651   -2.1498    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    0.4512    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    1.2112    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7665    1.4343   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5448    3.4885   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006    5.3678   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    3.3178    0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -0.0286   -1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261   -1.3590   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3989   -3.4580   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072   -4.7765   -0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6234   -1.5837   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6849   -0.1709   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 16  2  1  0
 23 18  1  0
 30 25  1  0
  9  4  1  0
 15 10  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 26 48  1  0
 27 49  1  0
 29 50  1  0
 30 51  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       0.956   8.801   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.075   7.657   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.462   8.481   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.516   2.391   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.516   3.931   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.401   6.192   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.938   7.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.182   1.621   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.182   4.701   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.112  -1.774   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.197   0.663   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.105  -0.190   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.432  -1.014   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.519  -2.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.604   0.036   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.581  -1.654   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.956  -2.478   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.545   0.384   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.877   1.595   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.951  -0.242   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.401   0.131   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.908   5.872   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.848   2.391   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.848   3.931   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.478   3.161   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.384   1.915   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.765  -1.495   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      -0.550  -2.799   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       2.384   4.407   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0      -0.062   3.161   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   22                                                       
CONECT    7    3   22                                                       
CONECT    8    4   23                                                       
CONECT    9    5   24                                                       
CONECT   10   14   20                                                       
CONECT   11   15   20                                                       
CONECT   12   16   21                                                       
CONECT   13   17   21                                                       
CONECT   14   10   27                                                       
CONECT   15   11   27                                                       
CONECT   16   12   28                                                       
CONECT   17   13   28                                                       
CONECT   18   20   26                                                       
CONECT   19   21   26                                                       
CONECT   20   10   11   18                                                  
CONECT   21   12   13   19                                                  
CONECT   22    6    7   29                                                  
CONECT   23    8   24   26                                                  
CONECT   24    9   23   29                                                  
CONECT   25   26   29   30                                                  
CONECT   26   18   19   23   25                                             
CONECT   27   14   15                                                       
CONECT   28   16   17                                                       
CONECT   29   22   24   25                                                  
CONECT   30   25                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

COMPND    HMDB0254104
HETATM    1  O1  UNL     1       0.603   1.603  -1.279  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.667   0.645  -0.455  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.863   0.132   0.048  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.200   0.500  -0.229  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.800   1.522   0.450  1.00  0.00           C  
HETATM    6  C4  UNL     1       5.112   1.903   0.195  1.00  0.00           C  
HETATM    7  C5  UNL     1       5.813   1.221  -0.773  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.239   0.189  -1.473  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.911  -0.166  -1.186  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.484  -0.909   0.959  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.290  -1.727   1.757  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.756  -2.667   2.612  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.388  -2.813   2.688  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.378  -2.001   1.897  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.133  -1.053   1.032  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.557  -0.068   0.087  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.315   0.901   0.886  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.799   2.138   0.297  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.059   2.250  -0.222  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.552   3.433  -0.798  1.00  0.00           C  
HETATM   21  N2  UNL     1      -2.749   4.509  -0.842  1.00  0.00           N  
HETATM   22  C19 UNL     1      -1.501   4.462  -0.347  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.015   3.298   0.220  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.118  -0.805  -1.035  1.00  0.00           C  
HETATM   25  C22 UNL     1      -2.282  -1.636  -0.984  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.294  -2.980  -0.589  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.436  -3.748  -0.595  1.00  0.00           C  
HETATM   28  N3  UNL     1      -4.590  -3.230  -0.984  1.00  0.00           N  
HETATM   29  C25 UNL     1      -4.656  -1.969  -1.373  1.00  0.00           C  
HETATM   30  C26 UNL     1      -3.515  -1.172  -1.376  1.00  0.00           C  
HETATM   31  H1  UNL     1       3.273   2.077   1.216  1.00  0.00           H  
HETATM   32  H2  UNL     1       5.613   2.705   0.713  1.00  0.00           H  
HETATM   33  H3  UNL     1       6.829   1.482  -1.002  1.00  0.00           H  
HETATM   34  H4  UNL     1       5.809  -0.327  -2.223  1.00  0.00           H  
HETATM   35  H5  UNL     1       3.498  -0.980  -1.757  1.00  0.00           H  
HETATM   36  H6  UNL     1       3.362  -1.627   1.711  1.00  0.00           H  
HETATM   37  H7  UNL     1       2.399  -3.298   3.228  1.00  0.00           H  
HETATM   38  H8  UNL     1      -0.041  -3.538   3.348  1.00  0.00           H  
HETATM   39  H9  UNL     1      -1.465  -2.150   2.004  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.200   0.451   1.418  1.00  0.00           H  
HETATM   41  H11 UNL     1      -0.632   1.211   1.751  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.767   1.434  -0.189  1.00  0.00           H  
HETATM   43  H13 UNL     1      -4.545   3.489  -1.198  1.00  0.00           H  
HETATM   44  H14 UNL     1      -0.901   5.368  -0.412  1.00  0.00           H  
HETATM   45  H15 UNL     1      -0.028   3.318   0.618  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.311  -0.029  -1.867  1.00  0.00           H  
HETATM   47  H17 UNL     1      -0.226  -1.359  -1.522  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.399  -3.458  -0.280  1.00  0.00           H  
HETATM   49  H19 UNL     1      -3.407  -4.776  -0.283  1.00  0.00           H  
HETATM   50  H20 UNL     1      -5.623  -1.584  -1.685  1.00  0.00           H  
HETATM   51  H21 UNL     1      -3.685  -0.171  -1.741  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4   10
CONECT    4    5    5    9
CONECT    5    6   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   35
CONECT   10   11   11   15
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16
CONECT   16   17   24
CONECT   17   18   40   41
CONECT   18   19   19   23
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   22
CONECT   22   23   23   44
CONECT   23   45
CONECT   24   25   46   47
CONECT   25   26   26   30
CONECT   26   27   48
CONECT   27   28   28   49
CONECT   28   29
CONECT   29   30   30   50
CONECT   30   51
END

HMDB0254104
     RDKit          3D
Linopirdine
 51 55  0  0  0  0  0  0  0  0999 V2000
    0.6033    1.6030   -1.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6668    0.6453   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631    0.1322    0.0483 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996    0.5002   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000    1.5225    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1121    1.9026    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8135    1.2209   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2392    0.1891   -1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.1664   -1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4845   -0.9094    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2897   -1.7266    1.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -2.6672    2.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -2.8125    2.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -2.0012    1.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334   -1.0526    1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -0.0685    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147    0.9014    0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7987    2.1382    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590    2.2500   -0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5517    3.4326   -0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493    4.5085   -0.8421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    4.4621   -0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0152    3.2981    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -0.8052   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816   -1.6356   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -2.9795   -0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4362   -3.7482   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5901   -3.2303   -0.9843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -1.9690   -1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5152   -1.1718   -1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    2.0766    1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6133    2.7047    0.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8291    1.4824   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095   -0.3268   -2.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983   -0.9799   -1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -1.6272    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3993   -3.2984    3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -3.5384    3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651   -2.1498    2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    0.4512    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    1.2112    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7665    1.4343   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5448    3.4885   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9006    5.3678   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    3.3178    0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -0.0286   -1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261   -1.3590   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3989   -3.4580   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072   -4.7765   -0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6234   -1.5837   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6849   -0.1709   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 16  2  1  0
 23 18  1  0
 30 25  1  0
  9  4  1  0
 15 10  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 26 48  1  0
 27 49  1  0
 29 50  1  0
 30 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3-Dipyridylmethyl-1-phenyl-2-indolinone	MeSH
DuP-996	MeSH
3,3-Bis(4-pyridylmethyl)-1-phenylindolin-2-one	MeSH
DuP 996	MeSH
Linopirdine	MeSH

Chemical Formula

C₂₆H₂₁N₃O

Average Molecular Weight

391.474

Monoisotopic Molecular Weight

391.168462308

IUPAC Name

1-phenyl-3,3-bis[(pyridin-4-yl)methyl]-2,3-dihydro-1H-indol-2-one

Traditional Name

linopirdine

CAS Registry Number

Not Available

SMILES

O=C1N(C2=CC=CC=C2C1(CC1=CC=NC=C1)CC1=CC=NC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H21N3O/c30-25-26(18-20-10-14-27-15-11-20,19-21-12-16-28-17-13-21)23-8-4-5-9-24(23)29(25)22-6-2-1-3-7-22/h1-17H,18-19H2

InChI Key

YEJCDKJIEMIWRQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Monocyclic benzene moiety
Pyridine
Benzenoid
Tertiary carboxylic acid amide
Heteroaromatic compound
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:34823 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0254104)

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	3.49	ALOGPS
logP	4.41	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	5.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.63 m³·mol⁻¹	ChemAxon
Polarizability	41.76 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	185.219	30932474
DeepCCS	[M-H]-	182.861	30932474
DeepCCS	[M-2H]-	216.649	30932474
DeepCCS	[M+Na]+	191.795	30932474
AllCCS	[M+H]+	196.7	32859911
AllCCS	[M+H-H2O]+	193.9	32859911
AllCCS	[M+NH4]+	199.2	32859911
AllCCS	[M+Na]+	199.9	32859911
AllCCS	[M-H]-	197.6	32859911
AllCCS	[M+Na-2H]-	196.9	32859911
AllCCS	[M+HCOO]-	196.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Linopirdine	O=C1N(C2=CC=CC=C2C1(CC1=CC=NC=C1)CC1=CC=NC=C1)C1=CC=CC=C1	4926.4	Standard polar	33892256
Linopirdine	O=C1N(C2=CC=CC=C2C1(CC1=CC=NC=C1)CC1=CC=NC=C1)C1=CC=CC=C1	3506.9	Standard non polar	33892256
Linopirdine	O=C1N(C2=CC=CC=C2C1(CC1=CC=NC=C1)CC1=CC=NC=C1)C1=CC=CC=C1	3332.2	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 - Linopirdine GC-MS (Non-derivatized) - 70eV, Positive	splash10-022c-8489000000-c910a42b0f7bb9c071d3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linopirdine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linopirdine LC-ESI-qTof , Positive-QTOF	splash10-00di-4790000000-dc2de63175e77d9642cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linopirdine LC-ESI-qTof , Positive-QTOF	splash10-0uk9-2394000000-3aacc997a328a33b28ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linopirdine , positive-QTOF	splash10-0006-0029000000-42da3f807bfa9d739d26	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linopirdine , positive-QTOF	splash10-0fka-2394000000-3d83fcab8a361968eb7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linopirdine , positive-QTOF	splash10-00di-4790000000-dc2de63175e77d9642cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linopirdine , positive-QTOF	splash10-0uk9-2394000000-3aacc997a328a33b28ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linopirdine 35V, Positive-QTOF	splash10-0fdo-3069000000-bc552e4235fec96a6555	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 10V, Positive-QTOF	splash10-0006-0009000000-396f1d01b611951d8c0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 20V, Positive-QTOF	splash10-0006-0119000000-64e15f3125366788d223	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 40V, Positive-QTOF	splash10-016v-9612000000-9e078b5c51f4a9285562	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 10V, Negative-QTOF	splash10-0006-0009000000-211dd6c8fdad962e0d78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 20V, Negative-QTOF	splash10-0006-0009000000-b3af5078331824fcee31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 40V, Negative-QTOF	splash10-03xv-4359000000-fee8625f4efde1ed5602	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 10V, Positive-QTOF	splash10-0006-0009000000-45fd988f0c3558f4066e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 20V, Positive-QTOF	splash10-0006-1009000000-5738c56427327218a4fc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 40V, Positive-QTOF	splash10-0005-2679000000-849863d8ffae09282fab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 10V, Negative-QTOF	splash10-0006-0009000000-1bcf9bb1d24a060f28e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 20V, Negative-QTOF	splash10-0006-1009000000-e99ae6d6fb6967de8433	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linopirdine 40V, Negative-QTOF	splash10-00ko-3809000000-a9c2c1ed1c9480f5fba2	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

DB13806

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C13780

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Linopirdine

METLIN ID

Not Available

PubChem Compound

3932

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 ]

Enzymes

Enzyme Details

1. Potassium voltage-gated channel subfamily KQT member 2

General function:: Involved in potassium channel activity
Specific function:: Probably important in the regulation of neuronal excitability. Associates with KCNQ3 to form a potassium channel with essentially identical properties to the channel underlying the native M-current, a slowly activating and deactivating potassium conductance which plays a critical role in determining the subthreshold electrical excitability of neurons as well as the responsiveness to synaptic inputs. KCNQ2/KCNQ3 current is blocked by linopirdine and XE991, and activated by the anticonvulsant retigabine. Muscarinic agonist oxotremorine-M strongly suppress KCNQ2/KCNQ3 current in cells in which cloned KCNQ2/KCNQ3 channels were coexpressed with M1 muscarinic receptors
Gene Name:: KCNQ2
Uniprot ID:: O43526
Molecular weight:: 95846.6

Enzyme Details

2. Potassium voltage-gated channel subfamily KQT member 5

General function:: Involved in ion channel activity
Specific function:: Probably important in the regulation of neuronal excitability. Associates with KCNQ3 to form a potassium channel which contributes to M-type current, a slowly activating and deactivating potassium conductance which plays a critical role in determining the subthreshold electrical excitability of neurons. May contribute, with other potassium channels, to the molecular diversity of an heterogeneous population of M-channels, varying in kinetic and pharmacological properties, which underlie this physiologically important current. Insensitive to tetraethylammonium, but inhibited by barium, linopirdine and XE991. Activated by niflumic acid and the anticonvulsant retigabine. Muscarine suppresses KCNQ5 current in Xenopus oocytes in which cloned KCNQ5 channels were coexpressed with M(1) muscarinic receptors
Gene Name:: KCNQ5
Uniprot ID:: Q9NR82
Molecular weight:: 102178.0

Showing metabocard for Linopirdine (HMDB0254104)

MOL for HMDB0254104 (Linopirdine)

3D MOL for HMDB0254104 (Linopirdine)

3D SDF for HMDB0254104 (Linopirdine)

3D-SDF for HMDB0254104 (Linopirdine)

PDB for HMDB0254104 (Linopirdine)

3D PDB for HMDB0254104 (Linopirdine)

SMILES for HMDB0254104 (Linopirdine)

INCHI for HMDB0254104 (Linopirdine)

Structure for HMDB0254104 (Linopirdine)

3D Structure for HMDB0254104 (Linopirdine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes