(1R,3R)-9-methoxy-1-methyl-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione

ID: ALA3103854

PubChem CID: 76324723

Max Phase: Preclinical

Molecular Formula: C24H21N3O4

Molecular Weight: 415.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)C1=C(C[C@H](Cn3cc(-c4ccccc4)nn3)O[C@@H]1C)C2=O

Standard InChI:  InChI=1S/C24H21N3O4/c1-14-21-18(23(28)17-9-6-10-20(30-2)22(17)24(21)29)11-16(31-14)12-27-13-19(25-26-27)15-7-4-3-5-8-15/h3-10,13-14,16H,11-12H2,1-2H3/t14-,16-/m1/s1

Standard InChI Key:  RHGXPWJMJQUARQ-GDBMZVCRSA-N

Molfile:  

     RDKit          2D

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    2.5235  -11.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195  -11.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264  -12.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5335  -12.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9411  -12.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9293  -11.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389  -11.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6474  -12.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3519  -12.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0524  -12.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0439  -11.7230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349  -11.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222  -10.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463  -13.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7638  -12.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252  -10.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4677  -12.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5196  -10.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099  -10.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2161  -12.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7574  -12.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3423  -11.5306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5446  -11.7079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5710  -12.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9774  -12.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7903  -12.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1966  -12.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7840  -11.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9725  -11.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
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  3  4  2  0
  4  6  1  0
  5  6  2  0
  5  8  1  0
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  7 10  1  0
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  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
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  8 15  2  0
  7 16  2  0
 12 17  1  1
 14 18  1  1
 17 19  1  0
  1 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  2  0
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 24 25  2  0
 25 19  1  0
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 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103854

   (1R,3R)-9-methoxy-1-methyl-3-[(4-phenyltriazol-1-yl)methyl]-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione

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: 415.45

Molecular Weight (Monoisotopic): 415.1532

AlogP: 3.51

#Rotatable Bonds: 4

Polar Surface Area: 83.31

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.37

CX LogD: 3.37

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: 0.03

References

1. Heapy AM, Patterson AV, Smaill JB, Jamieson SM, Guise CP, Sperry J, Hume PA, Rathwell K, Brimble MA..  (2013)  Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions.,  21  (24): [PMID:24436995] [10.1016/j.bmc.2013.09.052]

2. Röhrig UF, Majjigapu SR, Vogel P, Zoete V, Michielin O..  (2015)  Challenges in the Discovery of Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors.,  58  (24): [PMID:25970480] [10.1021/acs.jmedchem.5b00326]

3. Wang XX, Sun SY, Dong QQ, Wu XX, Tang W, Xing YQ..  (2019)  Recent advances in the discovery of indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors.,  10  (10): [PMID:32055299] [10.1039/C9MD00208A]

4. Singh R, Salunke DB..  (2021)  Diverse chemical space of indoleamine-2,3-dioxygenase 1 (Ido1) inhibitors.,  211  [PMID:33341650] [10.1016/j.ejmech.2020.113071]

Source

Source(1):

• Scientific Literature