Pachymic acid

Pachymic acid
Names
	IUPAC name 3-Acetoxy-16-hydroxy-24-methylenelanost-8-en-21-oic acid
	Systematic IUPAC name (2R)-2-[(3S,5R,10S,13R,14R,16R,17R)-3-acetyloxy-16-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Identifiers
CAS Number	29070-92-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL468034;
ChemSpider	280037 ;
KEGG	C17044;
PubChem CID	5484385;
UNII	X2FCK16QAH ;
CompTox Dashboard (EPA)	DTXSID10951675 ;
	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+ Key: JNUUNUQHXIOFDA-XTDASVJISA-N ; 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.[1]

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

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.
"Pachymic acid Biological Test Results". PubChem compound database. 3 March 2016.

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[PLoS_De_Novo_Sequencing-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.