(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-(propan-2-yl)(13,15,15-2H3)-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: 179018
• Molecular Formular: C20H24O6
• Molecular Mass: 360.40096
• Monoisotopic Mass: 360.15728849
• SMILES: C1C2=C([C@H]3[C@](C1)([C@@]14[C@@]5([C@H](C3)O5)[C@@H]([C@@]3([C@H]([C@H]1O4)O3)C(C)C)O)C)COC2=O
• Canonical SMILES: O=C1OCC2=C1CC[C@]1([C@H]2C[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,13S)-8-hydroxy-1-methyl-7-(propan-2-yl)(13,15,15-^2H₃)-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,13S)-8-hydroxy-7-isopropyl-1-methyl(13,15,15-^2H₃)-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: (3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-3b,4,4a,6,6a,7a,7b,8b,9,10-Decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one-d3; (-)-Triptolide-d3; Triptolid-d3; Triptolide-d3 (major, Contains d0)

Database IDs

• PubChem SID: 164234928
• PubChem CID: 71752738

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; Methanol
• Apperance: Off-White Solid
• Melting Point: 220-226°C

Safety Information

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

DETAILS

Toronto Research Chemicals - T815602

Labelled Triptolite (T815600), diterpenoid triepoxide with immunosuppressant and antitumor properties.

REFERENCES

• Hikim, S., et al.: J. Androl., 21, 431 (2000)
• Chang, W.-T., et al.: J. Biol. Chem., 276, 222 (2000)
• Kiviharju, T.M., et al.: Clin. Cancer Res., 8, 2666 (2000)
• Leuenroth, S.J., et al.: Chem. Biol., 12, 1259 (2000)