ID: ALA5315121

Max Phase: Approved

First Approval: 2018

Molecular Formula: C19H17F3N2O4

Molecular Weight: 376.33

Molecule Type: Small molecule

Representations

Synonyms Trade Names(2): Tecovirimat siga | Tpoxx

Canonical SMILES:  O.O=C(NN1C(=O)[C@@H]2[C@@H]3C=C[C@@H]([C@H]4C[C@@H]34)[C@@H]2C1=O)c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C19H15F3N2O3.H2O/c20-19(21,22)9-3-1-8(2-4-9)16(25)23-24-17(26)14-10-5-6-11(13-7-12(10)13)15(14)18(24)27;/h1-6,10-15H,7H2,(H,23,25);1H2/t10-,11+,12+,13-,14-,15+;

Standard InChI Key:  QRHXYGPOQKLBJP-NPIFKJBVSA-N

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: Yes

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 376.33

Molecular Weight (Monoisotopic): 376.1035

AlogP: 2.40

#Rotatable Bonds: 2

Polar Surface Area: 66.48

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.15

CX Basic pKa:

CX LogP: 2.07

CX LogD: 2.07

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.70

References

1. Unpublished dataset, 

2. Unpublished dataset, 

3. European Medicines Agency, 

Source

Source(3):

• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• European Medicines Agency