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2-[(1R,3R)-1-Methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid ID: ALA595201
PubChem CID: 45257251
Max Phase: Preclinical
Molecular Formula: C16H14O5
Molecular Weight: 286.28
Molecule Type: Small molecule
This compound is available for customization.
Associated Items:
Names and Identifiers Canonical SMILES: C[C@H]1O[C@@H](CC(=O)O)CC2=C1C(=O)c1ccccc1C2=O
Standard InChI: InChI=1S/C16H14O5/c1-8-14-12(6-9(21-8)7-13(17)18)15(19)10-4-2-3-5-11(10)16(14)20/h2-5,8-9H,6-7H2,1H3,(H,17,18)/t8-,9-/m1/s1
Standard InChI Key: VFSMYOQTRVFZER-RKDXNWHRSA-N
Molfile:
RDKit 2D
21 23 0 0 0 0 0 0 0 0999 V2000
-4.8433 -21.1228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.8445 -21.9466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1328 -22.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1345 -20.7118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.4222 -21.1191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.4188 -21.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7026 -22.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7094 -20.6991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9887 -21.1133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9877 -21.9445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2712 -22.3569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.5513 -21.9426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.5524 -21.1115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.2733 -20.6944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7140 -19.8777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-2.7005 -23.1798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.1601 -22.3535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2755 -19.8729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.8716 -21.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5831 -22.3536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.8717 -21.1213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4 1 1 0
5 6 1 0
2 3 1 0
3 6 2 0
9 14 1 0
10 11 1 0
11 12 1 0
12 13 1 0
13 14 1 0
1 2 2 0
8 15 2 0
5 8 1 0
7 16 2 0
6 7 1 0
12 17 1 1
7 10 1 0
14 18 1 1
9 8 1 0
17 19 1 0
9 10 2 0
19 20 1 0
5 4 2 0
19 21 2 0
M END Associated Targets(Human) Associated Targets(non-human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Calculated Properties Molecular Weight: 286.28Molecular Weight (Monoisotopic): 286.0841AlogP: 2.01#Rotatable Bonds: 2Polar Surface Area: 80.67Molecular Species: ACIDHBA: 4HBD: 1#RO5 Violations: ┄HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski): ┄CX Acidic pKa: 3.71CX Basic pKa: ┄CX LogP: 1.37CX LogD: -1.93Aromatic Rings: 1Heavy Atoms: 21QED Weighted: 0.90Np Likeness Score: 1.21
References 1. Sperry J, Lorenzo-Castrillejo I, Brimble MA, Machín F.. (2009) Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum., 17 (20): [PMID:19783445 ] [10.1016/j.bmc.2009.08.064 ] 2. Heapy AM, Patterson AV, Smaill JB, Jamieson SM, Guise CP, Sperry J, Hume PA, Rathwell K, Brimble MA.. (2013) Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions., 21 (24): [PMID:24436995 ] [10.1016/j.bmc.2013.09.052 ] 3. Yu, Xufen and 6 more authors. 2017-01-05 Synthesis, evaluation, and CoMFA study of fluoroquinophenoxazine derivatives as bacterial topoisomerase IA inhibitors. [PMID:27689733 ] 4. Klaeger, Susan S and 47 more authors. 2017-12-01 The target landscape of clinical kinase drugs. [PMID:29191878 ] 5. Abraham, Adedoyin D and 18 more authors. 2019-11-27 Drug Design Targeting T-Cell Factor-Driven Epithelial-Mesenchymal Transition as a Therapeutic Strategy for Colorectal Cancer. [PMID:31675229 ]