1-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrate hydrobromide

• ChemBase ID: 154662
• Molecular Formular: C20H22BrNO3
• Molecular Mass: 404.29758
• Monoisotopic Mass: 403.07830557
• SMILES: c1ccc2c(c1)cccc2CC1c2cc(c(cc2CCN1)O)O.O.Br
• Canonical SMILES: Oc1cc2CCNC(c2cc1O)Cc1cccc2c1cccc2.O.Br
• InChI: InChI=1S/C20H19NO2.BrH.H2O/c22-19-11-15-8-9-21-18(17(15)12-20(19)23)10-14-6-3-5-13-4-1-2-7-16(13)14;;/h1-7,11-12,18,21-23H,8-10H2;1H;1H2
• InChIKey: QHCUNMLYODPTIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrate hydrobromide
• IUPAC Traditional name: 1-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrate hydrobromide
• Synonyms: 1,2,3,4-Tetrahydro-1-(1-naphthalenylmethyl)-6,7-Isoquinolinediol hydrobromide monohydrate; YS-49 monohydrate

Database IDs

• CAS Number: 132836-42-1(anhydrous)
• MDL Number: MFCD16875442
• PubChem SID: 162248800
• PubChem CID: 71311929

CALCULATED PROPERTIES

• Acid pKa: 9.687348
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.95171845
• LogD (pH = 7.4): 2.3515866
• Log P: 3.5044541
• Molar Refractivity: 92.0654 cm^3
• Polarizability: 36.705853 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50
• Safety Statements: 61
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H19NO2 · HBr · H2O

DETAILS

Sigma Aldrich - Y1521

Biochem/physiol Actions
YS-49 protects cells from oxidant injury; anti-inflammatory agent; activator of PI3K/Akt signaling. YS-49, an analog of higenamine, induces heme oxygenase (HO-1) in endothelial cells and protects cells from oxidant injury. The compound was reported to inhibit Ang II-stimulated VSMC proliferation through HO-1 production, which inhibits both the JNK pathway and ROS production. A study (JPET) reported that CKD712 (S-YS-49) confer cardiac protection and anti-inflammatory via activation of the PI3K signal pathway. These effects were antagonized by a PI3K inhibitor, wortmannin.