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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:42:22 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240240

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Latrepirdine

Description

Latrepirdine belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position. In humans, latrepirdine is involved in the latrepirdine h1-antihistamine action pathway. Latrepirdine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Latrepirdine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0240240
     RDKit          3D
Latrepirdine
 49 52  0  0  0  0  0  0  0  0999 V2000
   -4.0711    4.3017    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339    3.2469    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    3.5963    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322    2.6280    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966    1.3043    0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355    0.9670    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4253    1.9438    0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052   -0.4116    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2001   -0.8770    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    0.1649    0.8178 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0613    0.0385    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    0.0530   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1450   -0.0747   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7483   -1.3192   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1252   -1.4460   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9344   -0.3314   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4239   -0.4424   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3294    0.8701   -0.2041 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9888    1.0189   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.3707    0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -2.9337   -0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -2.5109   -0.3546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894   -2.5521   -1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -1.4007    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228    5.3166    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174    4.2963    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6870    4.1470   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4519    4.6391    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270    2.8941    0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4609    1.6295    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600    0.8890    1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506   -0.8898    1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4163    1.0216   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -0.8150   -1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1337   -2.2073   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6138   -2.4234   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7937   -1.3801   -0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7173   -0.2707    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8912    0.3880   -0.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411    2.0083   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -2.5470    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -2.7663    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229   -4.0529   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -2.7459   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3178   -2.7040   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -3.4754   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6862   -1.7121   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5220   -0.9177    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -1.7851    1.5106 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
  7  2  1  0
 24  8  1  0
 10  5  1  0
 19 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
M  END


  Mrv1652309241721312D          

 24 27  0  0  0  0            999 V2000
    4.2575    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -1.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -2.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -3.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -4.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -3.9855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -5.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 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
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240240

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H25N3/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17/h4-7,12-13H,8-11,14H2,1-3H3

> <INCHI_KEY>
JNODQFNWMXFMEV-UHFFFAOYSA-N

> <FORMULA>
C21H25N3

> <MOLECULAR_WEIGHT>
319.452

> <EXACT_MASS>
319.204847817

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.59804615211325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2-{2,8-dimethyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-5-yl}ethyl)-2-methylpyridine

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.408522259333334

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.166283056454152

> <JCHEM_POLAR_SURFACE_AREA>
21.060000000000002

> <JCHEM_REFRACTIVITY>
100.72479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
latrepirdine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240240
     RDKit          3D
Latrepirdine
 49 52  0  0  0  0  0  0  0  0999 V2000
   -4.0711    4.3017    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339    3.2469    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    3.5963    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322    2.6280    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966    1.3043    0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355    0.9670    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4253    1.9438    0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052   -0.4116    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2001   -0.8770    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    0.1649    0.8178 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0613    0.0385    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    0.0530   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1450   -0.0747   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7483   -1.3192   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1252   -1.4460   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9344   -0.3314   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4239   -0.4424   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3294    0.8701   -0.2041 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9888    1.0189   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.3707    0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -2.9337   -0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -2.5109   -0.3546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894   -2.5521   -1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -1.4007    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228    5.3166    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174    4.2963    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6870    4.1470   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4519    4.6391    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270    2.8941    0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4609    1.6295    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600    0.8890    1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506   -0.8898    1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4163    1.0216   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -0.8150   -1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1337   -2.2073   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6138   -2.4234   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7937   -1.3801   -0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7173   -0.2707    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8912    0.3880   -0.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411    2.0083   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -2.5470    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -2.7663    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229   -4.0529   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -2.7459   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3178   -2.7040   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -3.4754   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6862   -1.7121   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5220   -0.9177    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -1.7851    1.5106 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
  7  2  1  0
 24  8  1  0
 10  5  1  0
 19 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
M  END

HEADER    PROTEIN                                 24-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-17         0                                  
HETATM    1  C   UNK     0       7.947   3.059   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.610  -2.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.944  -3.590   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.944  -5.130   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.277  -5.900   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.277  -7.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.944  -8.210   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.610  -7.440   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.610  -5.900   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.944  -9.750   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       0.303   1.914   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.727   3.059   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   23                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
CONECT   20    9   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22    8                                                       
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0240240
HETATM    1  C1  UNL     1      -4.071   4.302   0.660  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.034   3.247   0.709  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.712   3.596   0.838  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.732   2.628   0.885  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.097   1.304   0.801  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.436   0.967   0.671  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.425   1.944   0.623  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.505  -0.412   0.610  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.200  -0.877   0.705  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.380   0.165   0.818  1.00  0.00           N  
HETATM   11  C10 UNL     1       1.061   0.039   0.938  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.666   0.053  -0.449  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.145  -0.075  -0.369  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.748  -1.319  -0.387  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.125  -1.446  -0.314  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.934  -0.331  -0.220  1.00  0.00           C  
HETATM   17  C16 UNL     1       7.424  -0.442  -0.140  1.00  0.00           C  
HETATM   18  N2  UNL     1       5.329   0.870  -0.204  1.00  0.00           N  
HETATM   19  C17 UNL     1       3.989   1.019  -0.275  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.049  -2.371   0.659  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.935  -2.934  -0.404  1.00  0.00           C  
HETATM   22  N3  UNL     1      -3.288  -2.511  -0.355  1.00  0.00           N  
HETATM   23  C20 UNL     1      -3.989  -2.552  -1.598  1.00  0.00           C  
HETATM   24  C21 UNL     1      -3.574  -1.401   0.478  1.00  0.00           C  
HETATM   25  H1  UNL     1      -3.623   5.317   0.601  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.717   4.296   1.564  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.687   4.147  -0.250  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.452   4.639   0.902  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.327   2.894   0.988  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.461   1.629   0.521  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.460   0.889   1.528  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.351  -0.890   1.471  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.416   1.022  -0.927  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.292  -0.815  -1.024  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.134  -2.207  -0.460  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.614  -2.423  -0.327  1.00  0.00           H  
HETATM   37  H13 UNL     1       7.794  -1.380  -0.558  1.00  0.00           H  
HETATM   38  H14 UNL     1       7.717  -0.271   0.920  1.00  0.00           H  
HETATM   39  H15 UNL     1       7.891   0.388  -0.737  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.541   2.008  -0.258  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.010  -2.547   0.364  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.265  -2.766   1.673  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.923  -4.053  -0.291  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.439  -2.746  -1.386  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.318  -2.704  -2.468  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.639  -3.475  -1.575  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.686  -1.712  -1.752  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.522  -0.918   0.132  1.00  0.00           H  
HETATM   49  H25 UNL     1      -3.808  -1.785   1.511  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    7
CONECT    3    4   28
CONECT    4    5    5   29
CONECT    5    6   10
CONECT    6    7    7    8
CONECT    7   30
CONECT    8    9    9   24
CONECT    9   10   20
CONECT   10   11
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   14   19
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   18
CONECT   17   37   38   39
CONECT   18   19   19
CONECT   19   40
CONECT   20   21   41   42
CONECT   21   22   43   44
CONECT   22   23   24
CONECT   23   45   46   47
CONECT   24   48   49
END

HMDB0240240
     RDKit          3D
Latrepirdine
 49 52  0  0  0  0  0  0  0  0999 V2000
   -4.0711    4.3017    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339    3.2469    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123    3.5963    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322    2.6280    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966    1.3043    0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355    0.9670    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4253    1.9438    0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052   -0.4116    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2001   -0.8770    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    0.1649    0.8178 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0613    0.0385    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656    0.0530   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1450   -0.0747   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7483   -1.3192   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1252   -1.4460   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9344   -0.3314   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4239   -0.4424   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3294    0.8701   -0.2041 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9888    1.0189   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.3707    0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -2.9337   -0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -2.5109   -0.3546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894   -2.5521   -1.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -1.4007    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228    5.3166    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174    4.2963    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6870    4.1470   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4519    4.6391    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270    2.8941    0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4609    1.6295    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600    0.8890    1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506   -0.8898    1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4163    1.0216   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -0.8150   -1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1337   -2.2073   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6138   -2.4234   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7937   -1.3801   -0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7173   -0.2707    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8912    0.3880   -0.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411    2.0083   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -2.5470    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -2.7663    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229   -4.0529   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -2.7459   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3178   -2.7040   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -3.4754   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6862   -1.7121   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5220   -0.9177    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -1.7851    1.5106 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
  7  2  1  0
 24  8  1  0
 10  5  1  0
 19 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  7 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dimebolin	HMDB
Dimeboline	HMDB
Dimebon	HMDB, MeSH
Dimebone	HMDB, MeSH
Preparation 84	HMDB
Latrepirdine	HMDB

Chemical Formula

C₂₁H₂₅N₃

Average Molecular Weight

319.452

Monoisotopic Molecular Weight

319.204847817

IUPAC Name

5-(2-{2,8-dimethyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-5-yl}ethyl)-2-methylpyridine

Traditional Name

latrepirdine

CAS Registry Number

3613-73-8

SMILES

CN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1

InChI Identifier

InChI=1S/C21H25N3/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17/h4-7,12-13H,8-11,14H2,1-3H3

InChI Key

JNODQFNWMXFMEV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

N-alkylindoles

Direct Parent

N-alkylindoles

Alternative Parents

Substituents

3-alkylindole
N-alkylindole
Indole
Methylpyridine
Aralkylamine
Pyridine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Amine
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240240)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Latrepirdine H1-Antihistamine Action (PathBank: SMP0062623)

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	3.52	ALOGPS
logP	3.41	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	7.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.72 m³·mol⁻¹	ChemAxon
Polarizability	38.6 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
AllCCS	[M+H]+	178.885	31661259
AllCCS	[M-H]-	187.614	31661259
DeepCCS	[M+H]+	177.349	30932474
DeepCCS	[M-H]-	174.991	30932474
DeepCCS	[M-2H]-	208.551	30932474
DeepCCS	[M+Na]+	183.778	30932474
AllCCS	[M+H]+	178.9	32859911
AllCCS	[M+H-H2O]+	175.6	32859911
AllCCS	[M+NH4]+	181.9	32859911
AllCCS	[M+Na]+	182.8	32859911
AllCCS	[M-H]-	187.6	32859911
AllCCS	[M+Na-2H]-	187.3	32859911
AllCCS	[M+HCOO]-	187.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.49 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2752 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	528.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	198.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	322.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	276.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	842.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	728.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	85.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	821.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	263.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	448.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	515.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	103.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Latrepirdine	CN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1	3706.4	Standard polar	33892256
Latrepirdine	CN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1	2786.4	Standard non polar	33892256
Latrepirdine	CN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1	2870.6	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 - Latrepirdine 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 - Latrepirdine 10V, Positive-QTOF	splash10-00di-0119000000-912c132b0c377d70b0b3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 20V, Positive-QTOF	splash10-00fr-1492000000-e074b38ea87239a8c292	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 40V, Positive-QTOF	splash10-00di-3900000000-abbbe3dcbd3e543a23a8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 10V, Negative-QTOF	splash10-014i-0009000000-71b046122676d3980bbc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 20V, Negative-QTOF	splash10-014j-4619000000-407ed46cd6f2005b6540	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 40V, Negative-QTOF	splash10-0032-0900000000-89c2c2376cf7c2758389	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 10V, Negative-QTOF	splash10-014i-0009000000-f70ad12b32e54f9e7e5e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 20V, Negative-QTOF	splash10-014i-0119000000-51575273a5c6e505932e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 40V, Negative-QTOF	splash10-0002-0900000000-889aeb417b06e468c4d6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 10V, Positive-QTOF	splash10-00di-0029000000-1a06bc7ad64cfd4a3cf3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 20V, Positive-QTOF	splash10-00fr-0296000000-a86db90723380799de1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Latrepirdine 40V, Positive-QTOF	splash10-00di-4930000000-a84c3182acd7a67506cf	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Latrepirdine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11725

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

170644

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Latrepirdine

METLIN ID

Not Available

PubChem Compound

197033

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

Montgomery LC, Deuster PA: Effects of antihistamine medications on exercise performance. Implications for sportspeople. Sports Med. 1993 Mar;15(3):179-95. [PubMed:7680815 ]

Showing metabocard for Latrepirdine (HMDB0240240)

MOL for HMDB0240240 (Latrepirdine)

3D MOL for HMDB0240240 (Latrepirdine)

3D SDF for HMDB0240240 (Latrepirdine)

3D-SDF for HMDB0240240 (Latrepirdine)

PDB for HMDB0240240 (Latrepirdine)

3D PDB for HMDB0240240 (Latrepirdine)

SMILES for HMDB0240240 (Latrepirdine)

INCHI for HMDB0240240 (Latrepirdine)

Structure for HMDB0240240 (Latrepirdine)

3D Structure for HMDB0240240 (Latrepirdine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra