3,4-dichloro-1H-isochromen-1-one

• ChemBase ID: 4039
• Molecular Formular: C9H4Cl2O2
• Molecular Mass: 215.03286
• Monoisotopic Mass: 213.95883473
• SMILES: Clc1c(Cl)c2ccccc2c(=O)o1
• Canonical SMILES: Clc1oc(=O)c2c(c1Cl)cccc2
• InChI: InChI=1S/C9H4Cl2O2/c10-7-5-3-1-2-4-6(5)9(12)13-8(7)11/h1-4H
• InChIKey: SUGXUUGGLDCZKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-dichloro-1H-isochromen-1-one
• IUPAC Traditional name: 3,4-dichloroisocoumarin; @3,4-dichloroisocoumarin
• Synonyms: 3,4-Dichloro-2-benzopyran-1-one; 3,4-DCI; 3,4-Dichloroisocoumarin; 3,4-Dichloroisocoumarin

Database IDs

• CAS Number: 51050-59-0
• MDL Number: MFCD00036960
• Beilstein Number: 6802625
• PubChem SID: 24278386; 46507031; 160967474
• PubChem CID: 1609

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.8767645
• LogD (pH = 7.4): 2.8767645
• Log P: 2.8767645
• Molar Refractivity: 61.0524 cm^3
• Polarizability: 19.454998 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.14
• LOG S: -3.49
• Solubility (Water): 6.97e-02 g/l

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C9H4Cl2O2

DETAILS

MP Biomedicals - 02158836

Reversible inhibitor of serine proteases, including chymotrypsin, trypsin, clotting factors XIa and XIIa. Also inhibits some endopeptidase such as protease (Staph. V-8). Does not inhibit papain.

DrugBank - DB04459

Drug information: experimental

Sigma Aldrich - D7910

Application
Useful in a rapid staining method for identification of macrophages; counts by this method were confirmed by the more complex morphological criteria, by phagocytosis, and by the presence of Fc receptors.1
Other Notes
Effective concentration 5-100 μM.
Quantity
Half-life = 20 min at pH 7.5.
Substrates
Serine protease inhibitor. Active towards a wide range of serine proteases including granzymes. Not active toward β-lactamases.

Sigma Aldrich - 35913

Other Notes
Effective concentration 5-100 μM.
Inhibitor of serine proteases1; Inhibition of porcine pancreatic elastase2
Quantity
Half-life = 20 min at pH 7.5.
Substrates
Serine protease inhibitor. Active towards a wide range of serine proteases including granzymes. Not active toward β-lactamases.
Biochem/physiol Actions
Inhibitor of serine proteases1 and porcine pancreatic elastase2. Treatment of proteasomes leads to rapid inactivation of chymotrypsin-like activity and slower inactivation of other proteases.3

REFERENCES

• Harper, J.W., et al., Biochemistry , 24 : 1831 (1985).