1-[(2-hydroxynaphthalen-1-yl)disulfanyl]naphthalen-2-ol

• ChemBase ID: 153919
• Molecular Formular: C20H14O2S2
• Molecular Mass: 350.45396
• Monoisotopic Mass: 350.04352169
• SMILES: c1ccc2c(c1)ccc(c2SSc1c2ccccc2ccc1O)O
• Canonical SMILES: Oc1ccc2c(c1SSc1c(O)ccc3c1cccc3)cccc2
• InChI: InChI=1S/C20H14O2S2/c21-17-11-9-13-5-1-3-7-15(13)19(17)23-24-20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H
• InChIKey: RFAXLXKIAKIUDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2-hydroxynaphthalen-1-yl)disulfanyl]naphthalen-2-ol
• IUPAC Traditional name: 1-[(2-hydroxynaphthalen-1-yl)disulfanyl]naphthalen-2-ol
• Synonyms: 1,1′-Disulfanediyldinaphthalen-2-ol; IPA-3; IPA-3

Database IDs

• CAS Number: 42521-82-4
• MDL Number: MFCD00388917
• PubChem SID: 162248058
• PubChem CID: 521106

CALCULATED PROPERTIES

• Acid pKa: 8.31782
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.944912
• LogD (pH = 7.4): 5.8950043
• Log P: 5.9455676
• Molar Refractivity: 99.3224 cm^3
• Polarizability: 42.39604 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: insoluble
• Apperance: off-white to yellow powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 41-50/53
• Safety Statements: 26-39-60-61
• GHS Pictograms: GHS05; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H318-H410
• GHS Precautionary statements: P273-P280-P305 + P351 + P338-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: PAK

Product Information

• Purity: ≥95% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C20H14O2S2

DETAILS

Sigma Aldrich - I2285

Biochem/physiol Actions
IPA-3 is an allosteric inhibitor of Pak1. It binds to autoinhibitory domain of Pak1 (p21 activated kinase), highly selective amongst kinases. Pak1 is implicated in tumorigenesis and metastasis.