Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:41:14 UTC

Update Date

2021-09-26 23:05:27 UTC

HMDB ID

HMDB0252705

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gevotroline

Description

Gevotroline, also known as wy 47384, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Based on a literature review a small amount of articles have been published on Gevotroline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Gevotroline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Gevotroline 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

HMDB0252705
     RDKit          3D
Gevotroline
 43 46  0  0  0  0  0  0  0  0999 V2000
   -5.5897   -3.3403   -1.3739 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2115   -2.1400   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1889   -1.3139   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8100   -0.0923    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4854    0.2942    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838    1.4063    0.6645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525    1.3032    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.1137   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -0.5228   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003   -1.7352   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311   -0.3053   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    0.5899   -0.2077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634   -0.0907   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.6185   -1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -1.3462   -1.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184   -0.4486   -0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886   -0.4223    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3282    0.3690    1.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173    1.1571    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445    1.1235   -0.8780 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.3384   -1.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350    1.4704    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4379    2.2356    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2388   -1.5940   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5643    0.5787    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3664    2.2080    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1584   -2.3949   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -0.5148   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7603   -1.3151   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.9265    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662    0.6228    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -1.3733   -1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    0.1731   -2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.2208   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4560   -1.6746   -2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -1.0366    1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4264    0.3578    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8729    1.7978    0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8976    0.3312   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    2.2405    0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0838    0.9745    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    3.0521   -0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    2.6884    1.7312 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12 22  1  0
 22 23  1  0
 10  2  1  0
 21 16  1  0
  9  5  1  0
 23  7  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  END

  Mrv1652309112112412D          

 23 26  0  0  0  0            999 V2000
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0025   -1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546   -2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996   -2.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517   -3.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967   -4.3937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7898   -4.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377   -3.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -3.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  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
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  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
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252705

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC2=C(NC3=C2CN(CCCC2=CN=CC=C2)CC3)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20FN3/c20-15-5-6-18-16(11-15)17-13-23(10-7-19(17)22-18)9-2-4-14-3-1-8-21-12-14/h1,3,5-6,8,11-12,22H,2,4,7,9-10,13H2

> <INCHI_KEY>
RZXHTPCHKSYGIB-UHFFFAOYSA-N

> <FORMULA>
C19H20FN3

> <MOLECULAR_WEIGHT>
309.388

> <EXACT_MASS>
309.164125819

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.09145002424681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-{8-fluoro-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-2-yl}propyl)pyridine

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.1273252366666657

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.985909908529102

> <JCHEM_PKA_STRONGEST_BASIC>
7.1480746884605715

> <JCHEM_POLAR_SURFACE_AREA>
31.92

> <JCHEM_REFRACTIVITY>
91.0128

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-{8-fluoro-1H,3H,4H,5H-pyrido[4,3-b]indol-2-yl}propyl)pyridine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0252705
     RDKit          3D
Gevotroline
 43 46  0  0  0  0  0  0  0  0999 V2000
   -5.5897   -3.3403   -1.3739 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2115   -2.1400   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1889   -1.3139   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8100   -0.0923    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4854    0.2942    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838    1.4063    0.6645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525    1.3032    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.1137   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -0.5228   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003   -1.7352   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311   -0.3053   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    0.5899   -0.2077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634   -0.0907   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.6185   -1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -1.3462   -1.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184   -0.4486   -0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886   -0.4223    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3282    0.3690    1.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173    1.1571    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445    1.1235   -0.8780 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.3384   -1.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350    1.4704    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4379    2.2356    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2388   -1.5940   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5643    0.5787    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3664    2.2080    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1584   -2.3949   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -0.5148   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7603   -1.3151   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.9265    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662    0.6228    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -1.3733   -1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    0.1731   -2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.2208   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4560   -1.6746   -2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -1.0366    1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4264    0.3578    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8729    1.7978    0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8976    0.3312   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    2.2405    0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0838    0.9745    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    3.0521   -0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    2.6884    1.7312 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12 22  1  0
 22 23  1  0
 10  2  1  0
 21 16  1  0
  9  5  1  0
 23  7  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.917  -0.374   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.410  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   14  F   UNK     0      -0.727  -1.519   0.000  0.00  0.00           F+0
HETATM   15  C   UNK     0       7.947  -1.519   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.471  -2.984   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.502  -4.128   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.026  -5.593   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.056  -6.737   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.581  -8.202   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       7.074  -8.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.044  -7.377   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.520  -5.913   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11                                                            
CONECT   15    3   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0252705
HETATM    1  F1  UNL     1      -5.590  -3.340  -1.374  1.00  0.00           F  
HETATM    2  C1  UNL     1      -5.211  -2.140  -0.851  1.00  0.00           C  
HETATM    3  C2  UNL     1      -6.189  -1.314  -0.328  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.810  -0.092   0.205  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.485   0.294   0.213  1.00  0.00           C  
HETATM    6  N1  UNL     1      -3.884   1.406   0.665  1.00  0.00           N  
HETATM    7  C5  UNL     1      -2.552   1.303   0.439  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.278   0.114  -0.166  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.485  -0.523  -0.310  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.900  -1.735  -0.833  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.931  -0.305  -0.546  1.00  0.00           C  
HETATM   12  N2  UNL     1       0.108   0.590  -0.208  1.00  0.00           N  
HETATM   13  C10 UNL     1       1.363  -0.091  -0.002  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.831  -0.618  -1.326  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.156  -1.346  -1.216  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.218  -0.449  -0.691  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.389  -0.422   0.680  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.328   0.369   1.277  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.117   1.157   0.440  1.00  0.00           C  
HETATM   20  N3  UNL     1       5.945   1.124  -0.878  1.00  0.00           N  
HETATM   21  C17 UNL     1       5.014   0.338  -1.463  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.135   1.470   0.886  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.438   2.236   0.738  1.00  0.00           C  
HETATM   24  H1  UNL     1      -7.239  -1.594  -0.321  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.564   0.579   0.624  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.366   2.208   1.113  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.158  -2.395  -1.247  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.840  -0.515  -1.654  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.760  -1.315  -0.065  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.251  -0.926   0.732  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.066   0.623   0.456  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.077  -1.373  -1.670  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.856   0.173  -2.074  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.077  -2.221  -0.547  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.456  -1.675  -2.227  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.772  -1.037   1.308  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.426   0.358   2.351  1.00  0.00           H  
HETATM   38  H15 UNL     1       6.873   1.798   0.881  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.898   0.331  -2.521  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.684   2.241   0.881  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.084   0.975   1.874  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.355   3.052  -0.006  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.649   2.688   1.731  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   10
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6    9
CONECT    6    7   26
CONECT    7    8    8   23
CONECT    8    9   11
CONECT    9   10   10
CONECT   10   27
CONECT   11   12   28   29
CONECT   12   13   22
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   17   17   21
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   38
CONECT   20   21   21
CONECT   21   39
CONECT   22   23   40   41
CONECT   23   42   43
END

HMDB0252705
     RDKit          3D
Gevotroline
 43 46  0  0  0  0  0  0  0  0999 V2000
   -5.5897   -3.3403   -1.3739 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2115   -2.1400   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1889   -1.3139   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8100   -0.0923    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4854    0.2942    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838    1.4063    0.6645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525    1.3032    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.1137   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -0.5228   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003   -1.7352   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311   -0.3053   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080    0.5899   -0.2077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3634   -0.0907   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.6185   -1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -1.3462   -1.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184   -0.4486   -0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886   -0.4223    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3282    0.3690    1.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173    1.1571    0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445    1.1235   -0.8780 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0135    0.3384   -1.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350    1.4704    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4379    2.2356    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2388   -1.5940   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5643    0.5787    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3664    2.2080    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1584   -2.3949   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -0.5148   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7603   -1.3151   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.9265    0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662    0.6228    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -1.3733   -1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    0.1731   -2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.2208   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4560   -1.6746   -2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -1.0366    1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4264    0.3578    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8729    1.7978    0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8976    0.3312   -2.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    2.2405    0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0838    0.9745    1.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    3.0521   -0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    2.6884    1.7312 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12 22  1  0
 22 23  1  0
 10  2  1  0
 21 16  1  0
  9  5  1  0
 23  7  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Fluoro-2,3,4,5-tetrahydro-2-[3-(3-pyridinyl)propyl]1H-pyrido[4,3-b]indole	ChEBI
Gevotrolina	ChEBI
Gevotrolinum	ChEBI
WY 47384	ChEBI
WY-47384	ChEBI
Gevotroline monohydrochloride	HMDB

Chemical Formula

C₁₉H₂₀FN₃

Average Molecular Weight

309.388

Monoisotopic Molecular Weight

309.164125819

IUPAC Name

3-(3-{8-fluoro-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-2-yl}propyl)pyridine

Traditional Name

3-(3-{8-fluoro-1H,3H,4H,5H-pyrido[4,3-b]indol-2-yl}propyl)pyridine

CAS Registry Number

Not Available

SMILES

FC1=CC2=C(NC3=C2CN(CCCC2=CN=CC=C2)CC3)C=C1

InChI Identifier

InChI=1S/C19H20FN3/c20-15-5-6-18-16(11-15)17-13-23(10-7-19(17)22-18)9-2-4-14-3-1-8-21-12-14/h1,3,5-6,8,11-12,22H,2,4,7,9-10,13H2

InChI Key

RZXHTPCHKSYGIB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aralkylamine
Aryl fluoride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary amine
Tertiary aliphatic amine
Azacycle
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.15	ALOGPS
logP	3.13	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.99	ChemAxon
pKa (Strongest Basic)	7.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	31.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.01 m³·mol⁻¹	ChemAxon
Polarizability	34.09 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+H]+	175.166	30932474
DeepCCS	[M-H]-	172.808	30932474
DeepCCS	[M-2H]-	206.045	30932474
DeepCCS	[M+Na]+	181.271	30932474
AllCCS	[M+H]+	175.2	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	178.2	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	179.2	32859911
AllCCS	[M+HCOO]-	178.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gevotroline	FC1=CC2=C(NC3=C2CN(CCCC2=CN=CC=C2)CC3)C=C1	3982.1	Standard polar	33892256
Gevotroline	FC1=CC2=C(NC3=C2CN(CCCC2=CN=CC=C2)CC3)C=C1	2684.2	Standard non polar	33892256
Gevotroline	FC1=CC2=C(NC3=C2CN(CCCC2=CN=CC=C2)CC3)C=C1	2979.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gevotroline,1TMS,isomer #1	C[Si](C)(C)N1C2=C(CN(CCCC3=CC=CN=C3)CC2)C2=CC(F)=CC=C21	2797.7	Semi standard non polar	33892256
Gevotroline,1TMS,isomer #1	C[Si](C)(C)N1C2=C(CN(CCCC3=CC=CN=C3)CC2)C2=CC(F)=CC=C21	2690.8	Standard non polar	33892256
Gevotroline,1TMS,isomer #1	C[Si](C)(C)N1C2=C(CN(CCCC3=CC=CN=C3)CC2)C2=CC(F)=CC=C21	3348.6	Standard polar	33892256
Gevotroline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=C(CN(CCCC3=CC=CN=C3)CC2)C2=CC(F)=CC=C21	2984.8	Semi standard non polar	33892256
Gevotroline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=C(CN(CCCC3=CC=CN=C3)CC2)C2=CC(F)=CC=C21	2903.7	Standard non polar	33892256
Gevotroline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=C(CN(CCCC3=CC=CN=C3)CC2)C2=CC(F)=CC=C21	3421.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gevotroline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w2c-3960000000-d18dea702f91964d2413	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gevotroline 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 - Gevotroline 10V, Positive-QTOF	splash10-03di-0009000000-67c9f190c2d4f84afe9b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gevotroline 20V, Positive-QTOF	splash10-03di-0009000000-c410b1d746bdddfd2600	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gevotroline 40V, Positive-QTOF	splash10-0600-3940000000-66b651dab2f60aaa8314	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gevotroline 10V, Negative-QTOF	splash10-0a4i-0009000000-a693f9e85c597a1ef660	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gevotroline 20V, Negative-QTOF	splash10-0a4i-0029000000-b52a8efbe9043c8ac8f5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gevotroline 40V, Negative-QTOF	splash10-069u-2921000000-91408f65c9530356d17a	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

54579

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gevotroline

METLIN ID

Not Available

PubChem Compound

60547

PDB ID

Not Available

ChEBI ID

142391

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 Gevotroline (HMDB0252705)

MOL for HMDB0252705 (Gevotroline)

3D MOL for HMDB0252705 (Gevotroline)

3D SDF for HMDB0252705 (Gevotroline)

3D-SDF for HMDB0252705 (Gevotroline)

PDB for HMDB0252705 (Gevotroline)

3D PDB for HMDB0252705 (Gevotroline)

SMILES for HMDB0252705 (Gevotroline)

INCHI for HMDB0252705 (Gevotroline)

Structure for HMDB0252705 (Gevotroline)

3D Structure for HMDB0252705 (Gevotroline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra