6-chloro-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-beta-carboline

ID: ALA4552312

Cas Number: 528816-57-1

PubChem CID: 3973224

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O

Molecular Weight: 312.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C2NCCc3c2[nH]c2ccc(Cl)cc32)cc1

Standard InChI:  InChI=1S/C18H17ClN2O/c1-22-13-5-2-11(3-6-13)17-18-14(8-9-20-17)15-10-12(19)4-7-16(15)21-18/h2-7,10,17,20-21H,8-9H2,1H3

Standard InChI Key:  BEIYDKMKDJZYSU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   31.1988  -25.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9000  -24.6576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8882  -23.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1752  -23.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2103  -25.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5063  -26.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5167  -27.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2302  -27.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9348  -27.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9210  -26.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4904  -24.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4757  -23.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7225  -24.9429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2331  -24.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6988  -23.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3573  -22.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5504  -22.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0862  -23.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4303  -24.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2039  -22.0879    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.2420  -28.3394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5402  -28.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  4  1  0
 11  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1  5  1  0
 11 12  2  0
 12 15  1  0
 14 13  1  0
 13 11  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
  8 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552312

   6-chloro-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 312.80

Molecular Weight (Monoisotopic): 312.1029

AlogP: 4.07

#Rotatable Bonds: 2

Polar Surface Area: 37.05

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.36

CX LogP: 3.82

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: -0.05

References

1. Tikhmyanova N, Paparoidamis N, Romero-Masters J, Feng X, Mohammed FS, Reddy PAN, Kenney SC, Lieberman PM, Salvino JM..  (2019)  Development of a novel inducer for EBV lytic therapy.,  29  (16): [PMID:31255485] [10.1016/j.bmcl.2019.06.034]

2. Baiazitov RY, Qi H, Arasu T, Lennox W, Cao L, Weetall M, Furia B, Zhuo J, Choi S, Kim MJ, Sheedy J, Davis T, Moon YC..  (2022)  SAR studies toward discovery of emvododstat (PTC299), a potent dihydroorotate dehydrogenase (DHODH) inhibitor.,  244  [PMID:36242990] [10.1016/j.ejmech.2022.114826]

Source

Source(1):

• Scientific Literature