Home Other Building Blocks 17,20,21-trihydroxy-4-pregnen-3-one

17,20,21-trihydroxy-4-pregnen-3-one

CAS No.:
5786-59-4
Catalog Number:
AG00EEFA
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG00EEFA
Chemical Name:
17,20,21-trihydroxy-4-pregnen-3-one
CAS Number:
5786-59-4
MDL Number:
MFCD30720159
IUPAC Name:
(8R,9S,10R,13S,14S,17R)-17-(1,2-dihydroxyethyl)-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
InChI:
InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-18,22,24-25H,3-10,12H2,1-2H3/t15-,16+,17+,18?,19+,20+,21+/m1/s1
InChI Key:
XNFSGLNHLVHCFT-WMSSUOLPSA-N
Properties
Complexity:
613  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
0
Exact Mass:
348.23g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
348.483g/mol
Monoisotopic Mass:
348.23g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
77.8A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
2  
Literature
Title Journal
Identification of 17,20β,21-trihydroxy-4-pregnen-3-one (20β-S) receptor binding and membrane progestin receptor alpha on southern flounder sperm (Paralichthys lethostigma) and their likely role in 20β-S stimulation of sperm hypermotility. General and comparative endocrinology 20110201
In vivo induction of oocyte maturation and ovulation in zebrafish. PloS one 20110101
Progestin signaling through mPRα in Atlantic croaker granulosa/theca cell cocultures and its involvement in progestin inhibition of apoptosis. Endocrinology 20101201
Synthesis of 17,20beta,21-trihydroxypregn-4-en-3-one by ovaries of reproductively mature Atlantic cod Gadus morhua. Journal of fish biology 20100701
Chronic hypoxia impairs gamete maturation in Atlantic croaker induced by progestins through nongenomic mechanisms resulting in reduced reproductive success. Environmental science & technology 20090601
Progestin signaling through an olfactory G protein and membrane progestin receptor-alpha in Atlantic croaker sperm: potential role in induction of sperm hypermotility. Endocrinology 20090101
Interference by atrazine and bisphenol-A with progestin binding to the ovarian progestin membrane receptor and induction of oocyte maturation in Atlantic croaker. Marine environmental research 20080701
Role of the tidal cycle in the gonadal development and spawning of the tropical wrasse Halichoeres trimaculatus. Zoological science 20080601
Hormonal regulation of the steroidogenic acute regulatory protein (StAR) in gonadal tissues of the Atlantic croaker (Micropogonias undulatus). General and comparative endocrinology 20070201
Tissue- and sex-specific regulation of CYP19A1 expression in the Atlantic croaker (Micropogonias undulatus). General and comparative endocrinology 20061101
Gonadotropin regulation of testosterone production by primary cultured theca and granulosa cells of Atlantic croaker: I. Novel role of CaMKs and interactions between calcium- and adenylyl cyclase-dependent pathways. General and comparative endocrinology 20060701
Steroid-induced oocyte maturation in Atlantic croaker (Micropogonias undulatus) is dependent on activation of the phosphatidylinositol 3-kinase/Akt signal transduction pathway. Biology of reproduction 20051101
Activation of a pertussis toxin-sensitive, inhibitory G-protein is necessary for steroid-mediated oocyte maturation in spotted seatrout. Developmental biology 20050901
Insulin-like growth factor-I induces oocyte maturational competence but not meiotic resumption in white bass (Morone chrysops) follicles in vitro: evidence for rapid evolution of insulin-like growth factor action. Biology of reproduction 20050501
Effects of external pH on hormonally regulated ovarian follicle maturation and ovulation in Atlantic croaker. General and comparative endocrinology 20050401
Identification of 17,20beta,21-trihydroxy-4-pregnen-3-one as an oocyte maturation-inducing steroid in black porgy, Acanthopagrus schlegeli. General and comparative endocrinology 20050201
Steroidogenesis in ovarian follicles of chub mackerel, Scomber japonicus. Zoological science 20050101
Binding characteristics, hormonal regulation and identity of the sperm membrane progestin receptor in Atlantic croaker. Steroids 20050101
Potential targets of transforming growth factor-beta1 during inhibition of oocyte maturation in zebrafish. Reproductive biology and endocrinology : RB&E 20050101
Disruption of rapid, nongenomic steroid actions by environmental chemicals: interference with progestin stimulation of sperm motility in Atlantic croaker. Environmental science & technology 20041201
Evidence that 4-pregnen-17,20beta,21-triol-3-one functions as a maturation-inducing hormone and pheromonal precursor in the percid fish, Gymnocephalus cernuus. General and comparative endocrinology 20041001
Steroid metabolism in vitro during final oocyte maturation in white croaker Micropogonias furnieri (Pisces: Sciaenidae). Brazilian journal of biology = Revista brasleira de biologia 20040501
Endocrine control of diurnal oocyte maturation in the kyusen wrasse, Halichoeres poecilopterus. Zoological science 20020901
Effects of the maturation-inducing steroid on LH secretion and the GnRH system at different stages of the gonadal cycle in Atlantic croaker. General and comparative endocrinology 20020501
Lunar synchronization of in vitro steroidogenesis in ovaries of the golden rabbitfish, Siganus guttatus (Bloch). General and comparative endocrinology 20020101
Effects of maturation-inducing hormone on heterologous gap junctional coupling in ovarian follicles of Atlantic croaker. General and comparative endocrinology 20011201
Plasma steroids in mature common dentex (Dentex dentex) stimulated with a gonadotropin-releasing hormone agonist. General and comparative endocrinology 20010701
In vitro hormone induction of final oocyte maturation in striped bass (Morone saxatilis) follicles is inhibited by blockers of phosphatidylinositol 3-kinase activity. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20010601
Steroid profiles in cultured female jundiá, the Siluridae Rhamdia quelen (Quoy and Gaimard, Pisces Teleostei), during the first reproductive cycle. General and comparative endocrinology 20010301
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