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 ;
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 [citation needed]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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] Pachymic acid is a white powder that is not absorbed well by the body due the poor solubility it has in water.^[2]

Effects

Pachymic acid is known to inhibit the Epstein–Barr virus and to inhibit the snake venom phospholipase A2.^[3] It also has antitumor and anti-inflammatory properties.^[1] Pachymic acid anti-tumor properties are due to the cytotoxic effects it has on the tumors making them less viable and proliferate less. Various cancer cells can have their cell growth stopped and undergo apotosis, however the exact mechanism is not known.^[2]^[4]

References

^ ^a ^b 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.
^ ^a ^b Wei, Chunyong; Wang, Hezhen; Sun, Xun; Bai, Zhixun; Wang, Jing; Bai, Guohui; Yao, Qizheng; Xu, Yingshu; Zhang, Lei (2022-07-01). "Pharmacological profiles and therapeutic applications of pachymic acid (Review)". Experimental and Therapeutic Medicine. 24 (3). doi:10.3892/etm.2022.11484. ISSN 1792-0981. PMC 9366251.
^ "Pachymic acid Biological Test Results". PubChem compound database. 3 March 2016.
^ Jiang, Feng; Zhu, Tieming; Yang, Chunfeng; Chen, Yang; Fu, Zhidong; Jiang, Lihui; Liu, Yongzhi (2023). "Pachymic Acid Inhibits Growth and Metastatic Potential in Liver Cancer HepG2 and Huh7 Cells". Biological and Pharmaceutical Bulletin. 46 (1): 35–41. doi:10.1248/bpb.b22-00440.

[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.

[:0-2] Wei, Chunyong; Wang, Hezhen; Sun, Xun; Bai, Zhixun; Wang, Jing; Bai, Guohui; Yao, Qizheng; Xu, Yingshu; Zhang, Lei (2022-07-01). "Pharmacological profiles and therapeutic applications of pachymic acid (Review)". Experimental and Therapeutic Medicine. 24 (3). doi:10.3892/etm.2022.11484. ISSN 1792-0981. PMC 9366251.

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

[4] Jiang, Feng; Zhu, Tieming; Yang, Chunfeng; Chen, Yang; Fu, Zhidong; Jiang, Lihui; Liu, Yongzhi (2023). "Pachymic Acid Inhibits Growth and Metastatic Potential in Liver Cancer HepG2 and Huh7 Cells". Biological and Pharmaceutical Bulletin. 46 (1): 35–41. doi:10.1248/bpb.b22-00440.

[1]

[2]

[3]

[4]