Pachymic acid

Pachymic acid is a naturally occurring steroid that can be extracted from the parasitic fungus Wolfiporia extensa (synonym Wolfiporia cocos). The dried sclerotia of the fungus is used as a traditional Chinese medicine, and pachymic acid is thought to be the principal bioactive component of it.[1]

Pachymic acid
Names
IUPAC name
3β-(Acetyloxy)-16α-hydroxy-24-methylidenelanost-8-en-21-oic acid
Systematic IUPAC name
(2R)-2-[(1R,2R,3aR,5aR,6S,9aS,11aR)-7-(Acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]-6-methyl-5-methylideneheptanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+ checkY
    Key: JNUUNUQHXIOFDA-XTDASVJISA-N checkY
  • InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h19,22,25-28,35H,3,10-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1
    Key: VDYCLYGKCGVBHN-DRCQUEPLSA-N
  • CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)OC(=O)C)C)C)C)O)C(=O)O
Properties
C33H52O5
Molar mass 528.76 g/mol
Density 1.1±0.1 g/cm3
Boiling point 612.2±55.0 °C at 760 mmHg
Hazards
Flash point 184.7±25.0 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Effects

Pachymic acid is known to inhibit the Epstein–Barr virus and to inhibit the snake venom phospholipase A2.[2] It also has antitumor and anti-inflammatory properties.[1]

References
  1. Shu, Shaohua; Chen, Bei; Zhou, Mengchun; Zhao, Xinmei; Xia, Haiyang; Wang, Mo (2013). "De Novo Sequencing and Transcriptome Analysis of Wolfiporia cocos to Reveal Genes Related to Biosynthesis of Triterpenoids". PLOS ONE. 8 (8): e71350. Bibcode:2013PLoSO...871350S. doi:10.1371/journal.pone.0071350. PMC 3743799. PMID 23967197.
  2. "Pachymic acid Biological Test Results". PubChem compound database. 3 March 2016.


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