(6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate hydrate

• ChemBase ID: 154800
• Molecular Formular: C32H48O9
• Molecular Mass: 576.71812
• Monoisotopic Mass: 576.32983312
• SMILES: CC(=O)OC(C)(C)/C=C/C(=O)C(C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@@H](C(=O)C2(C)C)O)C)C)C)O)O.O
• Canonical SMILES: CC(=O)OC(/C=C/C(=O)C([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@H](O)C(=O)C2(C)C)C)C)(O)C)(C)C.O
• InChI: InChI=1S/C32H46O8.H2O/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7;/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3;1H2/t19-,20+,21-,22+,25+,29+,30-,31+,32+;/m1./s1
• InChIKey: YBFJWXSFAMCEAY-BOUKRGDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate hydrate
• IUPAC Traditional name: (6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate hydrate
• Synonyms: (2β,9β,10α,16α,23E)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-Norlanosta-5,23-diene-3,11,22-trione; Cucurbitacin B hydrate

Database IDs

• CAS Number: 6199-67-3(anhydrous)
• MDL Number: MFCD18432707
• PubChem SID: 162248938
• PubChem CID: 71311992

CALCULATED PROPERTIES

• Acid pKa: 12.802778
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 3.133085
• LogD (pH = 7.4): 3.1330833
• Log P: 3.133085
• Molar Refractivity: 151.0433 cm^3
• Polarizability: 59.152073 Å^3
• Polar Surface Area: 138.2 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: off-white to light brown powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C32H46O8 · xH2O

DETAILS

Sigma Aldrich - C8499

Biochem/physiol Actions
Cucurbitacin B is a triterpenoid constituent of Cucurbitaceae plant species. Cucurbitacin B inhibits proliferation in a wide variety of tumor cell lines (IC50 15-30 nM) by inducing apoptosis and inducing cell cycle arrest at G2/M phase. Although the mechanism of action is unclear, Cucurbitacin B inhibits STAT 3 phosphorylation and expression levels and has been shown to block JAK2 activity. Curcubitacin B also inhibits the transcriptional activity of HIF1a and Nf-KB. Curcubitacin B is structurally similar to the JAK inhibitor Curcubitacin I.