7-Methoxy-1-[(E)-2-(4-nitro-phenyl)-vinyl]-9H-beta-carboline

ID: ALA112452

Cas Number: 17019-08-8

PubChem CID: 6250668

Max Phase: Preclinical

Molecular Formula: C20H15N3O3

Molecular Weight: 345.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: TCMDC-125486 | TCMDC-125486 | TCMDC-125486|17019-08-8|NSC371712|CHEMBL112452|SCHEMBL12305583|DTXSID30422251|NSC-371712|7-methoxy-1-[(E)-2-(4-nitrophenyl)vinyl]-9H-pyrido[3,4-b]indole|9H-pyrido[3,4-b]indole, 7-methoxy-1-[(E)-2-(4-nitrophenyl)ethenyl]-

Canonical SMILES:  COc1ccc2c(c1)[nH]c1c(/C=C/c3ccc([N+](=O)[O-])cc3)nccc12

Standard InChI:  InChI=1S/C20H15N3O3/c1-26-15-7-8-16-17-10-11-21-18(20(17)22-19(16)12-15)9-4-13-2-5-14(6-3-13)23(24)25/h2-12,22H,1H3/b9-4+

Standard InChI Key:  RACKRQSOLIUNNO-RUDMXATFSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    3.6402   -8.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391   -9.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3539  -10.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3521   -8.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0675   -8.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -9.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598   -9.9111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8520   -8.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3373   -9.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1531   -9.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4846   -8.3965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9942   -7.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1802   -7.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6406   -9.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9243  -10.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -9.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3080  -10.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7956  -11.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4609  -11.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9477  -12.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7688  -12.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1007  -11.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6118  -11.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2606  -13.2291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0806  -13.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9290  -13.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  2  0
 13  8  1  0
  3  6  2  0
 10 14  1  0
  6  7  1  0
  2 15  1  0
  7  9  1  0
 15 16  1  0
  8  5  1  0
 14 17  2  0
  1  2  2  0
 17 18  1  0
  5  4  2  0
 18 19  2  0
  8  9  2  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 10 11  2  0
 11 12  1  0
 24 25  2  0
 24 26  1  0
 21 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA112452

   7-methoxy-1-[(E)-2-(4-nitrophenyl)vinyl]-9H-pyrido[3,4-b]indole

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: 345.36

Molecular Weight (Monoisotopic): 345.1113

AlogP: 4.80

#Rotatable Bonds: 4

Polar Surface Area: 81.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: 5.07

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.43

Np Likeness Score: -0.15

References

1. Ishida J, Wang HK, Bastow KF, Hu CQ, Lee KH..  (1999)  Antitumor agents 201. Cytotoxicity of harmine and beta-carboline analogs.,  9  (23): [PMID:10612592] [10.1016/s0960-894x(99)00598-3]

2. Ishida J, Wang HK, Oyama M, Cosentino ML, Hu CQ, Lee KH..  (2001)  Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives.,  64  (7): [PMID:11473435] [10.1021/np0101189]

3. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

4. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

5. Luo B, Song X..  (2021)  A comprehensive overview of β-carbolines and its derivatives as anticancer agents.,  224  [PMID:34332400] [10.1016/j.ejmech.2021.113688]

Source

Source(3):

• Scientific Literature
• GSK Malaria Screening
• St Jude Leishmania Screening