Cyanine-863

ID: ALA2074851

PubChem CID: 70686871

Max Phase: Preclinical

Molecular Formula: C24H26ClN3

Molecular Weight: 356.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cyanine-863 | CHEMBL2074851|Cyanine-863

Canonical SMILES:  CC[n+]1c(CC2C=C(C)N=C(c3ccccc3)N2C)ccc2ccccc21.[Cl-]

Standard InChI:  InChI=1S/C24H26N3.ClH/c1-4-27-21(15-14-19-10-8-9-13-23(19)27)17-22-16-18(2)25-24(26(22)3)20-11-6-5-7-12-20;/h5-16,22H,4,17H2,1-3H3;1H/q+1;/p-1

Standard InChI Key:  QOYNJNDPPQNAPL-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
  -12.7580   -0.2062    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  -14.9973    3.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7118    2.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7118    1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9973    1.5321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2828    1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2828    2.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.4263    1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1408    1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1408    2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.4263    3.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5684    1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8539    1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1394    1.5321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4249    1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4249    2.7697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1394    3.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8539    2.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7105    1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7105    0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9960    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2815    0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2815    1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9960    1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1394    4.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1394    0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9973    0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2829    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  2  7  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  3 11  1  0
  3  4  1  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 18 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 15 19  1  0
 19 20  1  0
 19 24  2  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 17 25  1  0
 14 26  1  0
  5 27  1  0
 27 28  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: 356.49

Molecular Weight (Monoisotopic): 356.2121

AlogP: 4.35

#Rotatable Bonds: 4

Polar Surface Area: 19.48

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.91

CX LogP: -0.29

CX LogD: -1.77

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.05

References

1. Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H..  (1996)  Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1.,  271  (1): [PMID:8955087] [10.1074/jbc.271.51.32599]

2. Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS..  (2002)  The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules.,  303  (1): [PMID:12438515] [10.1124/jpet.102.038885]

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. Martel F, Gründemann D, Calhau C, Schömig E..  (2001)  Apical uptake of organic cations by human intestinal Caco-2 cells: putative involvement of ASF transporters.,  363  (1): [PMID:11191835] [10.1007/s002100000335]

5. 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]

6. 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]

7. Martel F, Vetter T, Russ H, Gründemann D, Azevedo I, Koepsell H, Schömig E..  (1996)  Transport of small organic cations in the rat liver. The role of the organic cation transporter OCT1.,  354  (1): [PMID:8878062] [10.1007/bf00171063]

8. Pan BF, Sweet DH, Pritchard JB, Chen R, Nelson JA..  (1999)  A transfected cell model for the renal toxin transporter, rOCT2.,  47  (1): [PMID:10220855] [10.1093/toxsci/47.2.181]

Source

Source(1):

• TP-search Transporter Database