(1S,4S,7Z,16E,21R)-7-ethylidene-21-(propan-2-yl)-4-[(2H7)propan-2-yl](4-2H)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone

• ChemBase ID: 177530
• Molecular Formular: C24H36N4O6S2
• Molecular Mass: 540.69584
• Monoisotopic Mass: 540.20762689
• SMILES: C12C(=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)C2CSSCC/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-KXOYPWAYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,7Z,16E,21R)-7-ethylidene-21-(propan-2-yl)-4-[(^2H₇)propan-2-yl](4-^2H)-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: (1S,4S,7Z,16E,21R)-7-ethylidene-21-isopropyl-4-[(^2H₇)propan-2-yl](4-^2H)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
• Synonyms: Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl]-d8 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-d8 Cyclic (12)-Disulfide; Antibiotic FR 901228-d8; Chromadax-d8; FK 228-d8; FR 901228-d8; NSC 630176-d8; Romidepsin-d8

Database IDs

• PubChem SID: 164233440
• PubChem CID: 71752075

CALCULATED PROPERTIES

• 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
• Acid pKa: 10.671198
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.0779283
• LogD (pH = 7.4): 1.0777451
• Log P: 1.0779514

DETAILS

Toronto Research Chemicals - R425062

Labelled Romidepsin (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 inhibi

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)