(1R,2R,10S,11S,13R,14R,15R)-14-[(2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,7-diene-5,17-dione hydrate

• ChemBase ID: 153944
• Molecular Formular: C30H44O8
• Molecular Mass: 532.66556
• Monoisotopic Mass: 532.30361837
• SMILES: C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C=C(C(=O)C2(C)C)O)C)C)C(C)(C(=O)/C=C/C(C)(C)O)O)O.O
• Canonical SMILES: OC1=C[C@@H]2C(=CC[C@@H]3[C@@]2(C)C(=O)C[C@]2([C@@]3(C)C[C@H]([C@@H]2C(C(=O)/C=C/C(O)(C)C)(O)C)O)C)C(C1=O)(C)C.O
• InChI: InChI=1S/C30H42O7.H2O/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6;/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3;1H2/t17-,19-,20+,23+,27+,28-,29+,30+;/m1./s1
• InChIKey: ZKDSPEWKSJCXQE-NOOFPKBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,10S,11S,13R,14R,15R)-14-[(2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,7-diene-5,17-dione hydrate
• IUPAC Traditional name: (1R,2R,10S,11S,13R,14R,15R)-14-[(2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,7-diene-5,17-dione hydrate
• Synonyms: 2,16α,20,25-tetrahydroxy-9-methyl-19-Nor-9β,10α-lanosta-1,5,23-triene-3,11,22-trione; Elatericin B; JSI-124; NSC 521777; Cucurbitacin I hydrate; Cucurbitacin I

Database IDs

• CAS Number: 2222-07-3(anhydrous)
• EC Number: 218-736-8
• PubChem SID: 162248083
• PubChem CID: 71311763

CALCULATED PROPERTIES

• Acid pKa: 9.086396
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 3.0420787
• LogD (pH = 7.4): 3.0333438
• Log P: 3.0421913
• Molar Refractivity: 143.4603 cm^3
• Polarizability: 55.06341 Å^3
• Polar Surface Area: 132.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: white to off-white solid

Safety Information

• RTECS: RC6200000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C30H42O7 · xH2O

DETAILS

Sigma Aldrich - C4493

Biochem/physiol Actions
Cucurbitacin I (JSI-124) is a novel selective inhibitor of the janus kinase 2/signal transducer and activator of transcription 3 (JAK2/STAT3) signaling pathway with anti-proliferative and anti-tumor properties.