Basic information
- CAS
51050-59-0- Standard SMILES
O=c1oc(Cl)c(Cl)c2ccccc12- InChIKey
SUGXUUGGLDCZKB-UHFFFAOYSA-N- Molecular formula
- C9H4Cl2O2
- Average molar mass
- 215.03 g/mol
- Monoisotopic mass
- 213.9588348
Overview
3,4-dichloroisocoumarin is a member of the class of isocoumarins that is isocoumarin substituted by chloro groups at positions 3 and 4. It is a serine protease inhibitor. It has a role as a geroprotector and a serine protease inhibitor. It is an organochlorine compound and a member of isocoumarins.
Names & identifiers
- Preferred name
- 3,4-Dichloroisocoumarin
- IUPAC
- 3,4-dichloroisochromen-1-one
- English name
- 3,4-Dichloroisocoumarin
- Molecular formula
- C9H4Cl2O2
- Molecular weight
- 215.03
Names & synonyms
3,4-dichloroisocoumarin51050-59-03,4-Dichloro-1H-isochromen-1-one3,4-Dcl3,4-Dichloro-1H-2-benzopyran-1-one1H-2-Benzopyran-1-one, 3,4-dichloro-SD08W1HH6EDTXSID70199056NSC-727363CHEBI:109540RefChem:91034DTXCID00121547
Show more names
3,4-DICHLORO-2-BENZOPYRAN-1-ONE3,4 Dichloroisocoumarin, 10 mM in DMSO3,4-DCI, 3,4-Dichloro-2-benzopyran-1-one3,4-Dichloroisocoumarin - CAS 51050-59-0 - Calbiochem
637-085-43,4-dichloroisochromen-1-one3,4 dichloroisocoumarinMFCD000369603,4dichloroisocoumarinCHEMBL249833,4-DCISUGXUUGGLDCZKB-UHFFFAOYSA-N
Database identifiers
- CAS
51050-59-0- PubChem CID
- 1609
- DTXSID
DTXSID70199056- ChEMBL
CHEMBL24983- ChEBI
CHEBI:109540- UNII
- SD08W1HH6E
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 273
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 304.7 · 304.7±42.0 °C(Predicted)
- Density
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mM · Soluble in DMF or DMSO at a concentration of 10mM
- form
- White lyophilized solid
- color
- White to off-white
- BRN
- 6802625 · 6802625
- InChI
- 1S/C9H4Cl2O2/c10-7-5-3-1-2-4-6(5)9(12)13-8(7)11/h1-4H
- InChIKey
- SUGXUUGGLDCZKB-UHFFFAOYSA-N
- SMILES
- ClC1=C(Cl)c2ccccc2C(=O)O1
- FDA UNII
- 8 W1HH6E · SD08W1HH6E
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 3
- risk_code
- 25-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 26-36
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H301-H315-H319-H335
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationExogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES.
Applications
Description3,4-Dichloroisocoumarin (3,4-DCI) is a serine protease inhibitor. It completely inhibits enzyme activity of 24 serine proteases including human leukocyte elastase, thrombin, plasmin, Factor Xa, and Factor XIIa in vitro. 3,4-DCI stimulates caseinolytic activity of bovine pituitary multicatalytic proteinase complex (MPC) by inducing a conformational change in the MPC that exposes the caseinolytic active site. It has been used to functionally characterize the catalytic activities of multiple proteases including rat liver MPC and extracellular lipase.
UsesUseful 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. It is an inhibitor of Chymotrypsin and Trypsin. ,4 Dichloroisocoumarin also inhibits granzymes A, B, and H, cathepsin G, neutrophil elastase, proteinase and blocks apoptotic internucleosomal DNA cleavage in thymocytes without the involvement of endonucleases.
General DescriptionA potent irreversible inhibitor of serine proteases. Blocks apoptotic internucleosomal DNA cleavage in thymocytes without the involvement of endonucleases. Reacts with serine proteases to release an acylchloride moiety that can acylate another active site residue. Does not affect thiol proteases and metalloproteases. Also has no activity towards β-lactamases. Effective at concentrations ranging from 5-100 μM.
Suppliers35 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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