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(1S,3S,4S,5S)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylicacid

ID: ALA5286674

Max Phase: Preclinical

Molecular Formula: C16H18O9

Molecular Weight: 354.31

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)O[C@H]1C[C@](O)(C(=O)O)C[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16-/m0/s1

Standard InChI Key:  CWVRJTMFETXNAD-ZZVAFGPTSA-N

Molfile:  

 
     RDKit          2D

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   -3.2144   -1.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3559   -0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3561    0.7291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -2.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0705   -0.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    0.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    1.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144   -0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998   -1.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -0.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9124    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2620    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    2.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
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  8  9  1  0
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  9 13  1  0
 14 13  1  1
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 14 19  1  0
 19 20  1  6
 18 21  1  6
 16 22  1  0
 16 23  1  1
 22 24  2  0
 22 25  1  0
M  END

Alternative Forms

  1. Parent:

    ALA5286674

    ---

Associated Targets(Human)

ARG1 Tchem Arginase-1 (360 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

Biocomponents

Calculated Properties

Molecular Weight: 354.31Molecular Weight (Monoisotopic): 354.0951AlogP: -0.65#Rotatable Bonds: 4
Polar Surface Area: 164.75Molecular Species: ACIDHBA: 8HBD: 6
#RO5 Violations: 1HBA (Lipinski): 9HBD (Lipinski): 6#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.33CX Basic pKa: CX LogP: -0.27CX LogD: -3.69
Aromatic Rings: 1Heavy Atoms: 25QED Weighted: 0.23Np Likeness Score: 2.25

References

1. Zhang J, Zhang Y, Qu B, Yang H, Hu S, Dong X..  (2021)  If small molecules immunotherapy comes, can the prime be far behind?,  218  [PMID:33773287] [10.1016/j.ejmech.2021.113356]
2. Ilies, Monica; Di Costanzo, Luigi; North, Michelle L; Scott, Jeremy A and Christianson, David W.  2010-05-27  2-aminoimidazole amino acids as inhibitors of the binuclear manganese metalloenzyme human arginase I.  [PMID:20441173]
3. Ilies, Monica; Di Costanzo, Luigi; Dowling, Daniel P; Thorn, Katherine J and Christianson, David W.  2011-08-11  Binding of α,α-disubstituted amino acids to arginase suggests new avenues for inhibitor design.  [PMID:21728378]
4. Mitcheltree, Matthew J and 23 more authors.  2020-04-09  Discovery and Optimization of Rationally Designed Bicyclic Inhibitors of Human Arginase to Enhance Cancer Immunotherapy.  [PMID:32292567]
5. and Sabnis, Ram W.  2020-12-10  Novel Arginase Inhibitors for Treating Cancer and Respiratory Inflammatory Diseases.  [PMID:33335657]

Source