Itanapraced (CHF 5074) - Moligand™, ≥96% , Inhibitor of presenilin 1, CAS No.749269-83-8, Inhibitor of presenilin 1

CAS: 749269-83-8 Cat. No.: I413736 Molecular Weight: 325.16 EC Number: 633-291-3

GRADE & PURITY Moligand™, ≥96%

Synonyms

CSP1103 | CSP-1103 | GTPL7339 | SB16945 | 1-(3',4'-dichloro-2-fluoro[1,1'-biphenyl]-4-yl)-cyclopropanecarboxylic acid | NCGC00408905-01 | HMS3886F13 | 1-(3',4'-Dichloro-2-Fluorobiphenyl-4-Yl)cyclopropanecarboxylic Acid | UNII-C35RF1MWQZ | ITANAPRACED [WHO

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Itanapraced (CHF 5074) Itanapraced (CHF 5074, CSP-1103) is a gamma-secretase modulator that reduces Aβ42 and Aβ40 secretion. The IC50s of CHF5074 for inhibition of COX-1 and COX-2 is above 100 μmol/L.

Targets

γ secretase

In vitro

In human neuroglioma cells over-expressing the Swedish mutated APP [human neuroglioma cell line expressing APPswe (H4swe)], CHF5074 preferentially lowers Aβ42 secretion with an IC50 of 3.6 µmol/L. CHF5074 does not display inhibitory activity on COX-1 and COX-2 enzymes when employed at concentrations up to 100 µmol/L and 300 µmol/L respectively.

In vivo

In rats, CHF5074 is orally well absorbed (50%) and is slowly eliminated from plasma (t1/2 ≈ 20 h). In Tg2576 transgenic mice, chronic treatment with CHF5074 markedly reduces brain Aβ burden without histological signs of peripheral Notch-mediated toxicity.

Specifications

Synonyms

CSP1103 | CSP-1103 | GTPL7339 | SB16945 | 1-(3', 4'-dichloro-2-fluoro[1, 1'-biphenyl]-4-yl)-cyclopropanecarboxylic acid | NCGC00408905-01 | HMS3886F13 | 1-(3', 4'-Dichloro-2-Fluorobiphenyl-4-Yl)cyclopropanecarboxylic Acid | UNII-C35RF1MWQZ | ITANAPRACED [WHO

Specifications & Purity

Moligand™, ≥96%

Biochemical and Physiological Mechanisms

Itanapraced (CHF 5074, CSP-1103) is a gamma-secretase modulator that reduces Aβ42 and Aβ40 secretion. The IC50s of CHF5074 for inhibition of COX-1 and COX-2 is above 100 μmol/L.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of presenilin 1

Purity

≥96%

Names and Identifiers

• Pubchem Sid: 504765187
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765187
• Canonical Smiles: C1CC1(C2=CC(=C(C=C2)C3=CC(=C(C=C3)Cl)Cl)F)C(=O)O
• IUPAC Name: 1-[4-(3,4-dichlorophenyl)-3-fluorophenyl]cyclopropane-1-carboxylic acid
• InChIKey: LIYLTQQDABRNRX-UHFFFAOYSA-N
• INCHI: 1S/C16H11Cl2FO2/c17-12-4-1-9(7-13(12)18)11-3-2-10(8-14(11)19)16(5-6-16)15(20)21/h1-4,7-8H,5-6H2,(H,20,21)
• Isomeric SMILES: C1CC1(C2=CC(=C(C=C2)C3=CC(=C(C=C3)Cl)Cl)F)C(=O)O
• Molecular Weight: 325.16
• Reaxy-Rn: 10182271
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10182271&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Biphenyls and derivatives
        • Level5 Chlorinated biphenyls
          • Level6 Polychlorinated biphenyls

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Biphenyls and derivatives
• Intermediate Tree Nodes: Chlorinated biphenyls
• Direct Parent: Polychlorinated biphenyls
• Alternative Parents: Dichlorobenzenes Fluorobenzenes Cyclopropanecarboxylic acids Aryl fluorides Aryl chlorides Monocarboxylic acids and derivatives Carboxylic acids Organofluorides Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Polychlorinated biphenyl - 1,2-dichlorobenzene - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Cyclopropanecarboxylic acid - Cyclopropanecarboxylic acid or derivatives - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organofluoride - Organooxygen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organochloride - Organohalogen compound - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms attached to either benzene ring of the biphenyl moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PSEN1 Tchem Presenilin-1 (1 Activities)

Discover Target: PSEN1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APP Tclin Amyloid-beta A4 protein (8510 Activities)

Discover Target: APP

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Homo sapiens (32628 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Caco-2 (12174 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APH1A Tbio Gamma-secretase (4915 Activities)

Discover Target: APH1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

N2a (708 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAW264.7 (28094 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Brain (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasma (328 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 59 mg/mL (181.44 mM); Ethanol: 9 mg/mL (27.67 mM); Water: Insoluble
• Molecular Weight: 325.200 g/mol
• XLogP3: 4.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 324.012 Da
• Monoisotopic Mass: 324.012 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 413.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1