(5S,6R,7S,8S)-6,7,8-trihydroxy-2-(4-(trifluoromethyl)phenethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-5-carboxylic acid

ID: ALA5273557

Max Phase: Preclinical

Molecular Formula: C17H17F3N2O5

Molecular Weight: 386.33

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  O=C(O)[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)c2nc(CCc3ccc(C(F)(F)F)cc3)cn21

Standard InChI:  InChI=1S/C17H17F3N2O5/c18-17(19,20)9-4-1-8(2-5-9)3-6-10-7-22-11(16(26)27)12(23)13(24)14(25)15(22)21-10/h1-2,4-5,7,11-14,23-25H,3,6H2,(H,26,27)/t11-,12+,13-,14+/m0/s1

Standard InChI Key:  LZSIPXVQPVTVNE-RFQIPJPRSA-N

Molfile:  

 
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M  END

Alternative Forms

  1. Parent:

    ALA5273557

    ---

Associated Targets(Human)

HPSE Tchem Heparanase (634 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GUSB Tchem Beta-glucuronidase (537 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 386.33Molecular Weight (Monoisotopic): 386.1090AlogP: 1.08#Rotatable Bonds: 4
Polar Surface Area: 115.81Molecular Species: ACIDHBA: 6HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 3.42CX Basic pKa: 5.37CX LogP: -0.39CX LogD: -2.10
Aromatic Rings: 2Heavy Atoms: 27QED Weighted: 0.63Np Likeness Score: -0.14

References

1. Imai Y, Wakasugi D, Suzuki R, Kato S, Sugisaki M, Mima M, Miyagawa H, Endo M, Fujimoto N, Fukunaga T, Kato S, Kuroda S, Takahashi T, Kakinuma H..  (2023)  Lead identification of novel tetrahydroimidazo[1,2-a]pyridine-5-carboxylic acid derivative as a potent heparanase-1 inhibitor.,  79  [PMID:36368497] [10.1016/j.bmcl.2022.129050]

Source