N-(9-Phenylpropyl-b-carboline-3-carbonyl)-L-alanine

ID: ALA1097605

PubChem CID: 46193001

Max Phase: Preclinical

Molecular Formula: C24H23N3O3

Molecular Weight: 401.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)c1cc2c3ccccc3n(CCCc3ccccc3)c2cn1)C(=O)O

Standard InChI:  InChI=1S/C24H23N3O3/c1-16(24(29)30)26-23(28)20-14-19-18-11-5-6-12-21(18)27(22(19)15-25-20)13-7-10-17-8-3-2-4-9-17/h2-6,8-9,11-12,14-16H,7,10,13H2,1H3,(H,26,28)(H,29,30)/t16-/m0/s1

Standard InChI Key:  NDVFGDHSVYSORQ-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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    4.5556  -16.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3010  -14.9808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1679  -12.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6729  -13.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997  -14.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9854  -12.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3149  -13.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8215  -14.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8012  -15.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5210  -14.7448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5232  -13.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8095  -13.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2386  -13.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9521  -13.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2406  -12.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6676  -13.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6695  -12.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0965  -13.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3791  -14.7451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413  -17.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8198  -17.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128  -16.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3918  -17.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3770  -18.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892  -18.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8073  -18.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0
 14 15  2  0
 15 10  1  0
  8  9  1  0
 14 16  1  0
 16 17  1  0
  4  5  2  0
 16 18  2  0
  9  3  1  0
 17 19  1  0
  3 11  1  0
 19 20  1  0
 10  8  1  0
 19 21  1  1
  1  3  1  0
 20 22  1  0
  5  6  1  0
 20 23  2  0
 10 11  2  0
 24  2  1  0
  6  9  2  0
 24 25  1  0
 11 12  1  0
 25 26  2  0
  1  2  1  0
 26 27  1  0
 12 13  2  0
 27 28  2  0
  8  7  2  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097605

   (2S)-2-[[9-(3-phenylpropyl)pyrido[3,4-b]indole-3-carbonyl]amino]propanoic acid

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: 401.47

Molecular Weight (Monoisotopic): 401.1739

AlogP: 4.03

#Rotatable Bonds: 7

Polar Surface Area: 84.22

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.61

CX Basic pKa: 1.90

CX LogP: 3.92

CX LogD: 0.71

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -0.68

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