(1S,2S,4S,5S,7R,8R,9S,11S)-8-hydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one

• ChemBase ID: 133318
• Molecular Formular: C20H24O6
• Molecular Mass: 360.40096
• Monoisotopic Mass: 360.15728849
• SMILES: CC(C)[C@@]12[C@@H](O1)[C@H]1[C@@]3(O1)[C@]1(CCC4=C(C1C[C@H]1[C@]3([C@@H]2O)O1)COC4=O)C
• Canonical SMILES: O=C1OCC2=C1CC[C@]1(C2C[C@H]2[C@@]3([C@@]41O[C@H]4[C@@H]1O[C@@]1([C@H]3O)C(C)C)O2)C
• InChI: InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11?,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1
• InChIKey: DFBIRQPKNDILPW-KTGKZQHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4S,5S,7R,8R,9S,11S)-8-hydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^2,^4.0^2,^9.0^5,^7.0^9,^1^1.0^1^4,^1^8]icos-14(18)-en-17-one
• IUPAC Traditional name: (1S,2S,4S,5S,7R,8R,9S,11S)-8-hydroxy-7-isopropyl-1-methyl-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^2,^4.0^2,^9.0^5,^7.0^9,^1^1.0^1^4,^1^8]icos-14(18)-en-17-one
• Synonyms: PG 490; Triptolide

Database IDs

• CAS Number: 38748-32-2
• MDL Number: MFCD00210565
• PubChem SID: 162227595; 24900156
• PubChem CID: 16220015

CALCULATED PROPERTIES

• Acid pKa: 12.649559
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.3276725
• LogD (pH = 7.4): 1.3276701
• Log P: 1.3276726
• Molar Refractivity: 87.2606 cm^3
• Polarizability: 35.78344 Å^3
• Polar Surface Area: 84.12 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: white to off-white solid

Safety Information

• RTECS: YK7751000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Biological Source: from Tripterygium wilfordii

DETAILS

Sigma Aldrich - T3652

Biochem/physiol Actions
Triptolide is a diterpene triepoxide, the principal active ingredient in extracts from the Chinese herb Tripterygium wilfordii hook (TwHF). It is a potent immunosuppressant and anti-inflammatory. Triptolide has been shown to inhibit the expression of IL-2 in activated T cells at the level of purine-box/nuclear factor and NF-κB mediated transcription activation. It synergizes with cyclosporin A in promoting graft survival in animal models and in suppression of graft versus host disease in allogeneic bone marrow transplants. In addition, it induces apoptosis in tumor cells and potentiates tumor necrosis factor (TNFα) induction of apoptosis in part through the suppression of c-IAP2 and c-IAP1 induction.