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

ID: ALA5279462

Max Phase: Preclinical

Molecular Formula: C15H16N2O5

Molecular Weight: 304.30

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(Cc3ccccc3)cn21

Standard InChI:  InChI=1S/C15H16N2O5/c18-11-10(15(21)22)17-7-9(6-8-4-2-1-3-5-8)16-14(17)13(20)12(11)19/h1-5,7,10-13,18-20H,6H2,(H,21,22)/t10-,11+,12-,13+/m0/s1

Standard InChI Key:  QNIOIFHLCVBHRV-QNWHQSFQSA-N

Molfile:  

 
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M  END

Alternative Forms

  1. Parent:

    ALA5279462

    ---

Associated Targets(Human)

HPSE Tchem Heparanase (634 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: 304.30Molecular Weight (Monoisotopic): 304.1059AlogP: -0.13#Rotatable Bonds: 3
Polar Surface Area: 115.81Molecular Species: ACIDHBA: 6HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 3.51CX Basic pKa: 5.26CX LogP: -1.63CX LogD: -3.42
Aromatic Rings: 2Heavy Atoms: 22QED Weighted: 0.63Np Likeness Score: 0.37

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