(3aS)-3a-hydroxy-6-methyl-1-phenyl-1H,2H,3H,3aH,4H-pyrrolo[2,3-b]quinolin-4-one

• ChemBase ID: 1711
• Molecular Formular: C18H16N2O2
• Molecular Mass: 292.33184
• Monoisotopic Mass: 292.12117776
• SMILES: O=C1c2cc(C)ccc2N=C2[C@@]1(O)CCN2c1ccccc1
• Canonical SMILES: Cc1ccc2c(c1)C(=O)[C@]1(C(=N2)N(CC1)c1ccccc1)O
• InChI: InChI=1S/C18H16N2O2/c1-12-7-8-15-14(11-12)16(21)18(22)9-10-20(17(18)19-15)13-5-3-2-4-6-13/h2-8,11,22H,9-10H2,1H3/t18-/m1/s1
• InChIKey: LZAXPYOBKSJSEX-GOSISDBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS)-3a-hydroxy-6-methyl-1-phenyl-1H,2H,3H,3aH,4H-pyrrolo[2,3-b]quinolin-4-one
• IUPAC Traditional name: (S)-blebbistatin; @(S)-blebbistatin
• Synonyms: (-)-Blebbistatin; 1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2.3-b]-7-methylquinolin-4-one; (-)-Blebbistatin; (3aS)-1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one; (-)-1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2,3-b]-7-methylquinolin-4-one; (-)-Blebbistatin; (S)-(-)-Blebbistatin; (S)-blebbistatin

Database IDs

• CAS Number: 856925-71-8
• MDL Number: MFCD08460907
• PubChem SID: 46507910; 160965167
• PubChem CID: 5287792

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.537417
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.8787973
• LogD (pH = 7.4): 2.879484
• Log P: 2.8795247
• Molar Refractivity: 87.2451 cm^3
• Polarizability: 31.946686 Å^3
• Polar Surface Area: 52.9 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.0
• LOG S: -3.17
• Solubility (Water): 1.98e-01 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; chloroform: soluble; Dichloromethane; DMSO; DMSO: soluble >5 mg/mL; Ethyl Acetate; ethyl acetate: soluble; Methanol; methanol: soluble; methylene chloride: soluble
• Apperance: Bright Yellow Solid; solid
• Melting Point: >205°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H317-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Target: ATPase

Product Information

• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H16N2O2

DETAILS

DrugBank - DB01944

Drug information: experimental

Sigma Aldrich - B0560

Biochem/physiol Actions
(-)-Blebbistatin is a cell cycle inhibitor; selective inhibitor of non-muscle myosin II.

Toronto Research Chemicals - B592500

Blebbistatin blocked myosin II-dependent cell processes. It blocks cell blebbing rapidly and reversibly. Blebbistatin also rapidly disrupted directed cell migration and cytokinesis in vertebrate cell. Blebbistatin blocks both blebbing and cytokinesis

REFERENCES

• Straight, A.F., et al.: Science, 299, 1743 (2003)
• Duxbury, M.S., et al.: Biochem. Biophys. Res. Commun., 313, 992 (2003)
• Kovacs, M., et al.: J. Biol. Chem., 279, 34 35557 (2004)