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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)

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Type-2 restriction enzyme XhoI (19 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

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

Biocomponents

Calculated Properties

Molecular Weight: 286.28Molecular Weight (Monoisotopic): 286.0841AlogP: 2.01#Rotatable Bonds: 2
Polar 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: -1.93
Aromatic 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]

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