Triptonide

Not to be confused with Triptolide, another derivative of Tripterygium wilfordii.

Triptonide is a chemical compound found in Tripterygium wilfordii,^[1] a plant used in traditional Chinese medicine.^[2] A 2021 trial in mice and monkeys suggested that triptonide may offer a reversible male contraceptive.^[3][4]

Triptonide

Names
IUPAC name (1S,2S,4S,5S,7S,9S,11S,13S)-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)-ene-8,17-dione
Other names Triptonide; NSC 165677; 14-deoxy-14-oxo-triptolide
Identifiers
CAS Number	38647-11-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:132267
ChEMBL	ChEMBL205190
ChemSpider	58875
PubChem CID	65411
InChI InChI=1S/C20H22O6/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/h8,11-14H,4-7H2,1-3H3/t11-,12-,13-,14-,17-,18-,19+,20+/m0/s1 Key: SWOVVKGLGOOUKI-ZHGGVEMFSA-N
SMILES CC(C)[C@@]12[C@@H](O1)[C@H]3[C@@]4(O3)[C@]5(CCC6=C([C@@H]5C[C@H]7[C@]4(C2=O)O7)COC6=O)C
Properties
Chemical formula	C20H22O6
Molar mass	358.390 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

1. "Triptonide". pubchem.ncbi.nlm.nih.gov.
2. "Thunder God Vine". NCCIH.
3. Institute, The Lundquist (April 1, 2022). "Male Birth Control Pill: Natural Compound Discovered With "Ideal" Contraceptive Effects". SciTechDaily.
4. Chang, Zongliang; Qin, Weibing; Zheng, Huili; Schegg, Kathleen; Han, Lu; Liu, Xiaohua; Wang, Yue; Wang, Zhuqing; McSwiggin, Hayden; Peng, Hongying; Yuan, Shuiqiao; Wu, Jiabao; Wang, Yongxia; Zhu, Shenghui; Jiang, Yanjia; Nie, Hua; Tang, Yuan; Zhou, Yu; Hitchcock, Michael J. M.; Tang, Yunge; Yan, Wei (December 2021). "Triptonide is a reversible non-hormonal male contraceptive agent in mice and non-human primates". Nature Communications. 12 (1): 1253. Bibcode:2021NatCo..12.1253C. doi:10.1038/s41467-021-21517-5. PMC 7902613. PMID 33623031.