Mepiperphenidol

ID: ALA2074659

Cas Number: 520-20-7

PubChem CID: 10619

Max Phase: Unknown

Molecular Formula: C19H32BrNO

Molecular Weight: 290.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Darstine | Mepiperphenidol bromide | NSC-17126 | Mepiperphenidol bromide|Darstine|Mepiperphenidyl|Piperphenamine|Darstine bromide|520-20-7|NSC-17126|1-(3-Hydroxy-5-methyl-4-phenylhexyl)-1-methylpiperidinium bromide|E6OI36057B|NSC 17126|UNII-E6OI36057B|CHEMBL2074659|SCHEMBL16859838|DTXSID80966332|NSC17126|Piperidinium, 1-(3-hydroxy-5-methyl-4-phenylhexyl)-1-methyl-, bromide|Q27276940|1-(3-Hydroxy-5-methyl-4-phenylhexyl)-1-methylpiperidin-1-ium bromide|5-methyl-1-(1-methylpiperidin-1-ium-1-yl)-4-pShow More⌵

Canonical SMILES:  CC(C)C(c1ccccc1)C(O)CC[N+]1(C)CCCCC1.[Br-]

Standard InChI:  InChI=1S/C19H32NO.BrH/c1-16(2)19(17-10-6-4-7-11-17)18(21)12-15-20(3)13-8-5-9-14-20;/h4,6-7,10-11,16,18-19,21H,5,8-9,12-15H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  CALMOSBYAPVNLT-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    4.8161    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9475    1.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191    2.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194    1.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482    1.0686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2767    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9763    1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252    1.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018   -0.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268    1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643   -1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5768   -1.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643   -2.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -2.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -1.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107   -1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  2  7  1  0
  5  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 15 20  1  0
 12 15  1  0
 13 21  1  0
 11 22  1  0
  5  9  1  0
M  CHG  2   1  -1   5   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 290.47

Molecular Weight (Monoisotopic): 290.2478

AlogP: 3.81

#Rotatable Bonds: 6

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.58

CX LogD: -0.58

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: 0.21

References

1. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H..  (1997)  Cloning and characterization of two human polyspecific organic cation transporters.,  16  (1): [PMID:9260930] [10.1089/dna.1997.16.871]

2. Gründemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H..  (1994)  Drug excretion mediated by a new prototype of polyspecific transporter.,  372  (1): [PMID:7990927] [10.1038/372549a0]

3. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H..  (2001)  Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1.,  281  (1): [PMID:11502595] [10.1152/ajprenal.2001.281.3.f454]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• USP Dictionary of USAN and International Drug Names
• TP-search Transporter Database