Chemistry:Pachymic acid

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
CAS Number	29070-92-6 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL468034
ChemSpider	280037 Y
KEGG	C17044
PubChem CID	5484385
UNII	X2FCK16QAH Y
InChI 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+ Y Key: JNUUNUQHXIOFDA-XTDASVJISA-N Y 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
SMILES 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
Chemical formula	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

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.

Effects

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