20-Hydroxyecdysone

20-Hydroxyecdysone
Clinical data
Other names	BIO101
Pregnancy; category	unknown;
Routes of; administration	Oral
Legal status
Legal status	US: OTC; Not a regulated substance in general;
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	4-9 hours
Excretion	Urinary:?%
Identifiers
	IUPAC name (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one;
CAS Number	5289-74-7 ;
PubChem CID	5459840;
ChemSpider	4573597 ;
UNII	779A7KPL0Y;
ChEBI	CHEBI:16587 ;
ChEMBL	ChEMBL224128 ;
CompTox Dashboard (EPA)	DTXSID5040388 ;
ECHA InfoCard	100.241.312
Chemical and physical data
Formula	C27H44O7
Molar mass	480.642 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C;
	InChI InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1 ; Key:NKDFYOWSKOHCCO-YPVLXUMRSA-N ;
	(what is this?) (verify)

20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. A phytoecdysteroid produced by and extracted from various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides, it is belived to be a plant defense against herbivory that disrupts the reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals (including humans) lack this receptor, 20-hydroxyecdysone affects mammalian biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In mammals, it is hypothesized to bind to the estrogen receptor beta (ERβ) protein.

Clinical data


Other names	BIO101
Pregnancy category	unknown
Routes of administration	Oral
Legal status
Legal status	US: OTC Not a regulated substance in general
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	4-9 hours
Excretion	Urinary:?%
Identifiers
IUPAC name (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
CAS Number	5289-74-7^N
PubChem CID	5459840
ChemSpider	4573597^Y
UNII	779A7KPL0Y
ChEBI	CHEBI:16587^Y
ChEMBL	ChEMBL224128^Y
CompTox Dashboard (EPA)	DTXSID5040388
ECHA InfoCard	100.241.312
Chemical and physical data
Formula	C₂₇H₄₄O₇
Molar mass	480.642 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C
InChI InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1^Y Key:NKDFYOWSKOHCCO-YPVLXUMRSA-N^Y
^NY (what is this?) (verify)