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(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:
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:
RDKit 2D
22 24 0 0 0 0 0 0 0 0999 V2000
-2.2313 0.1626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5168 0.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.8024 0.1626 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.8024 -0.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5168 -1.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2313 -0.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.9455 -1.0747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.5168 -1.8995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.0197 -0.9082 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.4722 -0.2408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0015 0.4127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2969 -0.2408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5168 1.3998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.8026 1.8122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-2.2311 1.8122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-2.9455 0.5749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.7093 0.4734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2971 1.1878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7089 1.8995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5339 1.8995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9455 1.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5376 0.4734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
3 2 1 0
4 3 1 0
5 4 1 0
6 5 1 0
1 6 1 0
6 7 1 1
5 8 1 6
4 9 2 0
9 10 1 0
11 10 2 0
3 11 1 0
10 12 1 0
2 13 1 1
13 14 1 0
13 15 2 0
1 16 1 6
12 17 1 0
18 17 2 0
19 18 1 0
20 19 2 0
21 20 1 0
22 21 2 0
17 22 1 0
M END Associated Targets(Human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Topical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 304.30Molecular Weight (Monoisotopic): 304.1059AlogP: -0.13#Rotatable Bonds: 3Polar 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: -3.42Aromatic 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 ]