N-(4,4-azo-n-pentyl)-21-deoxyajmalinium

ID: ALA2074767

PubChem CID: 70686862

Max Phase: Preclinical

Molecular Formula: C25H35N4O+

Molecular Weight: 407.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1C[N+]2(CCCC3(C)N=N3)C3CC45c6ccccc6N(C)C4C2CC1C3C5O

Standard InChI:  InChI=1S/C25H35N4O/c1-4-15-14-29(11-7-10-24(2)26-27-24)19-12-16(15)21-20(29)13-25(23(21)30)17-8-5-6-9-18(17)28(3)22(19)25/h5-6,8-9,15-16,19-23,30H,4,7,10-14H2,1-3H3/q+1

Standard InChI Key:  JWNJXPKXYBPWQH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 36  0  0  0  0  0  0  0  0999 V2000
    5.3993   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9703   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9703   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3993   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1839   -7.6799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6688   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1839   -6.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3833   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978   -7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8123   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8123   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3833   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5267   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2412   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8842   -6.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9808   -6.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1799   -5.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3258   -4.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -4.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8122   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8122   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5267   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5267  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3236   -9.2740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1101  -10.0709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388   -8.4646    0.0000 C   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
  1  6  2  0
  1  9  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 15 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 11 18  1  0
  9 19  1  0
 19 18  1  0
 20  9  1  0
 18 21  1  0
 14 21  1  0
 21 20  1  0
 20 22  1  0
 11 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 28  2  0
  7 30  1  0
M  CHG  1  11   1
M  END

Alternative Forms

1. Parent:

   

   ALA2074767

   13-Ethyl-8-methyl-15-[3-(3-methyldiazirin-3-yl)propyl]-8-aza-15-azoniahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-ol

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: 407.58

Molecular Weight (Monoisotopic): 407.2805

AlogP: 3.71

#Rotatable Bonds: 5

Polar Surface Area: 48.19

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.06

CX LogD: -1.06

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.76

Np Likeness Score: 1.53

References

1. Renes J, de Vries EG, Nienhuis EF, Jansen PL, Müller M..  (1999)  ATP- and glutathione-dependent transport of chemotherapeutic drugs by the multidrug resistance protein MRP1.,  126  (1): [PMID:10188979] [10.1038/sj.bjp.0702360]

2. Müller M, Mayer R, Hero U, Keppler D..  (1994)  ATP-dependent transport of amphiphilic cations across the hepatocyte canalicular membrane mediated by mdr1 P-glycoprotein.,  343  (1): [PMID:7909523] [10.1016/0014-5793(94)80312-9]

3. van Montfoort JE, Müller M, Groothuis GM, Meijer DK, Koepsell H, Meier PJ..  (2001)  Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.,  298  (1): [PMID:11408531]

4. van Montfoort JE, Hagenbuch B, Fattinger KE, Müller M, Groothuis GM, Meijer DK, Meier PJ..  (1999)  Polyspecific organic anion transporting polypeptides mediate hepatic uptake of amphipathic type II organic cations.,  291  (1): [PMID:10490898]

Source

Source(1):

• TP-search Transporter Database