2-Benzyl-9-butyl-3-(carbonyl-valine ethyl ester)-bcarbolinium bromate

ID: ALA1095589

PubChem CID: 46193008

Max Phase: Preclinical

Molecular Formula: C30H36BrN3O3

Molecular Weight: 486.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c2ccccc2c2cc(C(=O)N[C@H](C(=O)OCC)C(C)C)[n+](Cc3ccccc3)cc21.[Br-]

Standard InChI:  InChI=1S/C30H35N3O3.BrH/c1-5-7-17-33-25-16-12-11-15-23(25)24-18-26(29(34)31-28(21(3)4)30(35)36-6-2)32(20-27(24)33)19-22-13-9-8-10-14-22;/h8-16,18,20-21,28H,5-7,17,19H2,1-4H3;1H/t28-;/m0./s1

Standard InChI Key:  KJGTVJPJAMESBE-JCOPYZAKSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7708   -3.5667    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1969   -6.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -7.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176   -5.8142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0846   -3.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896   -4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163   -5.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9021   -3.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2315   -4.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7382   -5.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111   -4.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0048   -5.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7179   -5.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4376   -5.5782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4398   -4.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7262   -4.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1553   -4.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688   -4.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1572   -3.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5842   -4.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2977   -4.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5862   -3.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0132   -4.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2958   -5.5784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -7.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -8.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3016   -3.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8727   -3.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7267   -4.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4421   -4.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502   -5.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465   -6.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4294   -7.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4254   -8.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1385   -8.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8572   -8.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8578   -7.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 17 18  1  0
 17 19  2  0
  2  3  1  0
 18 20  1  0
 10  4  1  0
 20 21  1  0
  4 12  1  0
 20 22  1  1
 11  9  1  0
 21 23  1  0
  5  6  2  0
 21 24  2  0
 25  3  1  0
 11 12  2  0
 25 26  1  0
  6  7  1  0
 22 27  1  0
 12 13  1  0
 22 28  1  0
  7 10  2  0
 23 29  1  0
 13 14  2  0
 29 30  1  0
  2  4  1  0
 14 31  1  0
 31 32  1  0
 14 15  1  0
 32 33  2  0
  9  8  2  0
 33 34  1  0
 15 16  2  0
 34 35  2  0
 16 11  1  0
 35 36  1  0
  8  5  1  0
 36 37  2  0
 37 32  1  0
 15 17  1  0
M  CHG  2   1  -1  14   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: 486.64

Molecular Weight (Monoisotopic): 486.2751

AlogP: 5.25

#Rotatable Bonds: 10

Polar Surface Area: 64.21

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.33

CX Basic pKa: ┄

CX LogP: 1.63

CX LogD: 1.63

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: -0.58

References

1. Ma C, Cao R, Shi B, Li S, Chen Z, Yi W, Peng W, Ren Z, Song H..  (2010)  Synthesis and cytotoxic evaluation of N2-benzylated quaternary beta-carboline amino acid ester conjugates.,  45  (4): [PMID:20122764] [10.1016/j.ejmech.2009.12.060]

Source

Source(1):

• Scientific Literature