(1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-bis(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

• ChemBase ID: 177529
• Molecular Formular: C24H36N4O6S2
• Molecular Mass: 540.69584
• Monoisotopic Mass: 540.20762689
• SMILES: [C@H]12C(=O)N/C(=C\C)/C(=O)N[C@H](C(=O)O[C@H](/C=C/CCSSC1)CC(=O)N[C@H](C(C)C)C(=O)N2)C(C)C
• Canonical SMILES: C/C=C/1\NC(=O)[C@H]2CSSCC/C=C/[C@@H](OC(=O)[C@@H](NC1=O)C(C)C)CC(=O)N[C@@H](C(=O)N2)C(C)C
• InChI: InChI=1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)/b9-7+,16-6-/t15-,17-,19-,20+/m1/s1
• InChIKey: OHRURASPPZQGQM-GCCNXGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-bis(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
• IUPAC Traditional name: romidepsin
• Synonyms: Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl] Cyclic (35)-Disulfide; [S-(E)]-N-(3-Hydroxy-7-mercapto-1-oxo-4-heptenyl)-D-valyl-D-cysteinyl-(Z)-2,3-didehydro-2-aminobutanoyl-L-valine (4-1)-Lactone Cyclic (12)-Disulfide; Antibiotic FR 901228; Chromadax; FK 228; FR 901228; NSC 630176; Romidepsin; Romidepsin (FK228 ,depsipeptide)

Database IDs

• CAS Number: 128517-07-7
• PubChem SID: 164233439
• PubChem CID: 5352062

CALCULATED PROPERTIES

• Acid pKa: 10.671198
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.0779485
• LogD (pH = 7.4): 1.0777453
• Log P: 1.0779514
• Molar Refractivity: 142.0856 cm^3
• Polarizability: 54.85299 Å^3
• Polar Surface Area: 142.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 219-224°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

Pharmacology Properties

• Target: HDAC

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - R425060

Romidepsin is a histone deacetylase inhibitor that can alter chromatin structure and gene transcription leading to multiple changes in cellular protein production. This may result in cell cycle arrest and tumor growth inhibition. Romidepsin has shown anti

REFERENCES

• Ueda, H., et al.: J. Antibiot., 47, 301 (1994)
• Weidle, U., et al.: Anticancer Res., 20, 1471 (1994)
• Kitazono, M., et al.: Cancer Res., 61, 6328 (1994)
• Sandor, V., et al.: Clin. Cancer Res., 8, 718 (1994)