tetramethylrosamine

ID: ALA541167

PubChem CID: 45267002

Max Phase: Preclinical

Molecular Formula: C24H24BrClN2O

Molecular Weight: 391.92

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tetramethylrosamine | CHEMBL541167

Canonical SMILES:  CN(C)c1ccc2c(-c3ccc(CCl)cc3)c3ccc(=[N+](C)C)cc-3oc2c1.[Br-]

Standard InChI:  InChI=1S/C24H24ClN2O.BrH/c1-26(2)18-9-11-20-22(13-18)28-23-14-19(27(3)4)10-12-21(23)24(20)17-7-5-16(15-25)6-8-17;/h5-14H,15H2,1-4H3;1H/q+1;/p-1

Standard InChI Key:  GKMBRSQQKZUCGD-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    9.0417   -4.4625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -5.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -3.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -2.5583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -6.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -3.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -7.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -6.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -8.2708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -7.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8625   -2.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750   -6.1292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8625   -8.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250   -8.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  2  0
  5  2  2  0
  6  2  1  0
  7  6  1  0
  8  7  2  0
  9  5  1  0
 10  3  1  0
 11  9  2  0
 12  7  1  0
 13 10  2  0
 14 12  2  0
 15  4  1  0
 16  8  1  0
 17 14  1  0
 18 16  2  0
 19 15  1  0
 20 15  2  0
 21 20  1  0
 22 19  2  0
 23 21  2  0
 24 11  1  0
 25 11  1  0
 26 29  1  0
 27 17  1  0
 28 17  1  0
 29 23  1  0
  8  4  1  0
  9 13  1  0
 18 14  1  0
 23 22  1  0
M  CHG  2   1  -1  11   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: 391.92

Molecular Weight (Monoisotopic): 391.1572

AlogP: 5.04

#Rotatable Bonds: 3

Polar Surface Area: 19.39

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.40

CX LogP: 1.07

CX LogD: 1.07

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: -0.21

References

1. Gannon MK, Holt JJ, Bennett SM, Wetzel BR, Loo TW, Bartlett MC, Clarke DM, Sawada GA, Higgins JW, Tombline G, Raub TJ, Detty MR..  (2009)  Rhodamine inhibitors of P-glycoprotein: an amide/thioamide "switch" for ATPase activity.,  52  (10): [PMID:19402665] [10.1021/jm900253g]

2. Muñoz-Martínez F, Lu P, Cortés-Selva F, Pérez-Victoria JM, Jiménez IA, Ravelo AG, Sharom FJ, Gamarro F, Castanys S..  (2004)  Celastraceae sesquiterpenes as a new class of modulators that bind specifically to human P-glycoprotein and reverse cellular multidrug resistance.,  64  (1): [PMID:15466210] [10.1158/0008-5472.can-04-1005]

3. Wang EJ, Casciano CN, Clement RP, Johnson WW..  (2003)  Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites.,  20  (1): [PMID:12739759] [10.1023/a:1023278211849]

Source

Source(2):

• Scientific Literature
• TP-search Transporter Database