Betulinic acid

Betulinic acid

Names
IUPAC name (3β)-3-Hydroxy-lup-20(29)-en-28-oic acid
Other names Betulic acid Mairin
Identifiers
CAS Number	472-15-1 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:3087 N
ChemSpider	58496 Y
ECHA InfoCard	100.006.773
EC Number	207-448-8
IUPHAR/BPS	3945
PubChem CID	64971
InChI InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1 Y Key: QGJZLNKBHJESQX-FZFNOLFKSA-N Y InChI=1/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1 Key: QGJZLNKBHJESQX-FZFNOLFKBI
SMILES O=C(O)[C@@]54[C@@H]([C@@H]3[C@@]([C@]1([C@@H]([C@]2(C)[C@@H](CC1)C(C)(C)[C@@H](O)CC2)CC3)C)(C)CC4)[C@H](C(=C)C)CC5
Properties
Chemical formula	C30H48O3
Molar mass	456.71 g·mol−1
Melting point	316 to 318 °C (601 to 604 °F; 589 to 591 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the ber tree (Ziziphus mauritiana), selfheal (Prunella vulgaris), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Pseudocydonia sinensis, former Chaenomeles sinensis KOEHNE),rosemary, and Pulsatilla chinensis.

In 1995, betulinic acid was reported as a selective inhibitor of human melanoma. Then it was demonstrated to induce apoptosis in human neuroblastoma in vitro and in vivo in model systems. At one time, it was undergoing drug development with assistance from the Rapid Access to Intervention Development program of the National Cancer Institute. Also, betulinic acid was found active in vitro against neuroectodermal (neuroblastoma, medulloblastoma, Ewing's sarcoma) and malignant brain tumors,ovarian carcinoma, in human leukemia HL-60 cells, and malignant head and neck squamous cell carcinoma SCC25 and SCC9 cell lines. In contrast, epithelial tumors, such as breast, colon, small cell lung and renal cell carcinomas, as well as T-cell leukemia cells, were completely unresponsive to treatment with betulinic acid.