2-Amino-4-(4-pentafluorothiophenyl)-4H-benzo[h]chromene-3-carbonitrile

ID: ALA4536562

PubChem CID: 155548499

Max Phase: Preclinical

Molecular Formula: C20H13F5N2OS

Molecular Weight: 424.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1=C(N)Oc2c(ccc3ccccc23)C1c1ccc(S(F)(F)(F)(F)F)cc1

Standard InChI:  InChI=1S/C20H13F5N2OS/c21-29(22,23,24,25)14-8-5-13(6-9-14)18-16-10-7-12-3-1-2-4-15(12)19(16)28-20(27)17(18)11-26/h1-10,18H,27H2

Standard InChI Key:  CISUNEDRLUOYCJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.5283  -16.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8230  -16.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1237  -17.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.6581  -17.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9474  -17.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3668  -17.4748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3628  -19.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0694  -19.5182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   25.6466  -21.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6457  -20.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9342  -22.3745    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.2259  -22.7821    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.6413  -22.7841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.9285  -23.1909    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.6383  -21.9610    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.2227  -21.9651    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536562

   ---

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: 424.39

Molecular Weight (Monoisotopic): 424.0669

AlogP: 6.72

#Rotatable Bonds: 2

Polar Surface Area: 59.04

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.68

CX LogP: 5.97

CX LogD: 5.97

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -0.71

References

1. Schmitt F, Gold M, Rothemund M, Andronache I, Biersack B, Schobert R, Mueller T..  (2019)  New naphthopyran analogues of LY290181 as potential tumor vascular-disrupting agents.,  163  [PMID:30503940] [10.1016/j.ejmech.2018.11.055]

2. Köhler LHF, Reich S, Yusenko M, Klempnauer KH, Shaikh AH, Ahmed K, Begemann G, Schobert R, Biersack B..  (2022)  A New Naphthopyran Derivative Combines c-Myb Inhibition, Microtubule-Targeting Effects, and Antiangiogenic Properties.,  13  (11.0): [PMID:36385941] [10.1021/acsmedchemlett.2c00403]

Source

Source(1):

• Scientific Literature