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Home > Other Building Blocks > 1247-64-9
1247-64-9 | Pregn-5-en-20-one, 3-(sulfooxy)-, (3β)-
CAS No: 1247-64-9 Catalog No: AG000MN2 MDL No:
Product Description
Catalog Number:
AG000MN2
Chemical Name:
Pregn-5-en-20-one, 3-(sulfooxy)-, (3β)-
CAS Number:
1247-64-9
Molecular Formula:
C21H32O5S
Molecular Weight:
396.5408
IUPAC Name:
[(3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
InChI:
InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15-,16-,17+,18-,19-,20-,21+/m0/s1
InChI Key:
DIJBBUIOWGGQOP-QGVNFLHTSA-N
SMILES:
CC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)OS(=O)(=O)O
UNII:
04Y4D91RG0
Properties
Complexity:
766
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
7
Defined Bond Stereocenter Count:
0
Exact Mass:
396.197g/mol
Formal Charge:
0
Heavy Atom Count:
27
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
396.542g/mol
Monoisotopic Mass:
396.197g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
89A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.8
Literature
| Title | Journal |
|---|---|
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| Neurosteroid modulation of glutamate release in hippocampal neurons: lack of an effect of a chronic prenatal ethanol exposure paradigm. | Alcoholism, clinical and experimental research 20030701 |
| Studies on neurosteroids XVI. Levels of pregnenolone sulfate in rat brains determined by enzyme-linked immunosorbent assay not requiring solvolysis. | Biological & pharmaceutical bulletin 20030501 |
| Conservation of the hydroxysteroid sulfotransferase SULT2B1 gene structure in the mouse: pre- and postnatal expression, kinetic analysis of isoforms, and comparison with prototypical SULT2A1. | Endocrinology 20030401 |
| Intact synaptic GABAergic inhibition and altered neurosteroid modulation of thalamic relay neurons in mice lacking delta subunit. | Journal of neurophysiology 20030301 |
| Hippocampal cytochrome P450s synthesize brain neurosteroids which are paracrine neuromodulators of synaptic signal transduction. | Biochimica et biophysica acta 20030217 |
| Studies on neurosteroids XV. Development of enzyme-linked immunosorbent assay for examining whether pregnenolone sulfate is a veritable neurosteroid. | Journal of pharmaceutical and biomedical analysis 20030115 |
| Seasonal changes in neurosteroid concentrations in the amphibian brain and environmental factors regulating their changes. | Brain research 20030110 |
| Pregnanolone isomers, pregnenolone and their polar conjugates around parturition. | Physiological research 20030101 |
| Increased neurosteroid sensitivity of hippocampal GABAA receptors during postnatal development. | Neuroscience 20030101 |
| Steroid modulation of angiotensin II action in the rat anterior pituitary gland. | Neuro endocrinology letters 20030101 |
| Effects of neurosteroids on epileptiform activity induced by picrotoxin and 4-aminopyridine in the rat hippocampal slice. | Epilepsy research 20030101 |
| Pharmacology of endogenous neuroactive steroids. | Critical reviews in neurobiology 20030101 |
| Inhibition by pregnenolone sulfate of nicotinic acetylcholine response in adrenal chromaffin cells. | European journal of pharmacology 20021205 |
| A caspase-3-dependent pathway is predominantly activated by the excitotoxin pregnenolone sulfate and requires early and late cytochrome c release and cell-specific caspase-2 activation in the retinal cell death. | Journal of neurochemistry 20021201 |
| Corticosterone acutely prolonged N-methyl-d-aspartate receptor-mediated Ca2+ elevation in cultured rat hippocampal neurons. | Journal of neurochemistry 20021201 |
| Regulation of N-methyl-D-aspartate cytotoxicity by neuroactive steroids in rat cortical neurons. | European journal of pharmacology 20021115 |
| Neurosteroid quantification in human brain regions: comparison between Alzheimer's and nondemented patients. | The Journal of clinical endocrinology and metabolism 20021101 |
| The neurosteroid pregnenolone sulfate infused into the medial septum nucleus increases hippocampal acetylcholine and spatial memory in rats. | Brain research 20021004 |
| Sulfonation and molecular action. | Endocrine reviews 20021001 |
| Neuroactive steroids, their precursors and polar conjugates during parturition and postpartum in maternal and umbilical blood: 3.3beta-hydroxy-5-ene steroids. | The Journal of steroid biochemistry and molecular biology 20021001 |
| Androgen biosynthesis in the quail brain. | Brain research 20020906 |
| Neurosteroids enhance spontaneous glutamate release in hippocampal neurons. Possible role of metabotropic sigma1-like receptors. | The Journal of biological chemistry 20020809 |
| Accumulation of 4- and 5-ene steroid sulfates in human breast cyst fluids. | The Journal of steroid biochemistry and molecular biology 20020701 |
| Low pregnenolone sulphate plasma concentrations in patients with generalized social phobia. | Psychological medicine 20020701 |
| Behavioral effects of chronic melatonin and pregnenolone injections in a myelin mutant rat (taiep). | The Journal of general psychology 20020701 |
| Neurosteroids enhance bandpass filter characteristics of the rat Schaffer collateral-to-CA1 synapse. | Neuroscience letters 20020621 |
| Reproductive hormonal treatments for mood disorders in women. | Dialogues in clinical neuroscience 20020601 |
| Gonadal steroids, brain, and behavior: role of context. | Dialogues in clinical neuroscience 20020601 |
| Gender differences in steroid modulation of angiotensin II-induced protein kinase C activity in anterior pituitary of the rat. | Biochemical and biophysical research communications 20020531 |
| Neuropeptide Y inhibits the biosynthesis of sulfated neurosteroids in the hypothalamus through activation of Y(1) receptors. | Endocrinology 20020501 |
| 3beta -hydroxypregnane steroids are pregnenolone sulfate-like GABA(A) receptor antagonists. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20020501 |
| Sex- and age-related changes in epitestosterone in relation to pregnenolone sulfate and testosterone in normal subjects. | The Journal of clinical endocrinology and metabolism 20020501 |
| Pregnenolone sulfate, dehydroepiandrosterone sulfate and allotetrahydrodeoxycorticosterone affect rapid tolerance to the hypothermic effect of ethanol. | Brain research bulletin 20020501 |
| Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta. | The Journal of clinical endocrinology and metabolism 20020401 |
| Two neuroactive steroids in midpregnancy as measured in maternal and fetal sera and in amniotic fluid. | Steroids 20020401 |
| Inhibition of the NMDA response by pregnenolone sulphate reveals subtype selective modulation of NMDA receptors by sulphated steroids. | British journal of pharmacology 20020201 |
| Studies on neurosteroids XIV. Levels of dehydroepiandrosterone sulfate in rat brain and serum determined with newly developed enzyme-linked immunosorbent assay. | Steroids 20011201 |
| Diminished allopregnanolone enhancement of GABA(A) receptor currents in a rat model of chronic temporal lobe epilepsy. | The Journal of physiology 20011201 |
| Differential involvement of the sigma(1) (sigma(1)) receptor in the anti-amnesic effect of neuroactive steroids, as demonstrated using an in vivo antisense strategy in the mouse. | British journal of pharmacology 20011201 |
| Steroid structure and pharmacological properties determine the anti-amnesic effects of pregnenolone sulphate in the passive avoidance task in rats. | The European journal of neuroscience 20011201 |
| Influence of neurosteroids on the development of rapid tolerance to ethanol in mice. | European journal of pharmacology 20011116 |
| Neuroactive steroids modulate crustacean locomotor activity. | Neuroscience letters 20011102 |
| Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators. | British journal of pharmacology 20011101 |
| Role of pregnenolone, dehydroepiandrosterone and their sulfate esters on learning and memory in cognitive aging. | Brain research. Brain research reviews 20011101 |
| Pregnenolone sulfate modulates angiotensin II-induced inositol 1,4,5-trisphosphate changes in the anterior pituitary of female rat. | Biochemical and biophysical research communications 20010928 |
| The antidepressant-like effect induced by sigma(1)-receptor agonists and neuroactive steroids in mice submitted to the forced swimming test. | The Journal of pharmacology and experimental therapeutics 20010901 |
| Pregnenolone sulfate and aging of cognitive functions: behavioral, neurochemical, and morphological investigations. | Hormones and behavior 20010901 |
| Neurosteroids stimulate G protein-coupled sigma receptors in mouse brain synaptic membrane. | Neuroscience research 20010901 |
| Metabotropic neurosteroid/sigma-receptor involved in stimulation of nociceptor endings of mice. | The Journal of pharmacology and experimental therapeutics 20010801 |
| Neurosteroid synthesis by cytochrome p450-containing systems localized in the rat brain hippocampal neurons: N-methyl-D-aspartate and calcium-dependent synthesis. | Endocrinology 20010801 |
| Effect of treatment of hypothyroidism on the plasma concentrations of neuroactive steroids and homocysteine. | Clinical chemistry and laboratory medicine 20010801 |
| Homocysteine in breast cyst fluid. | European journal of clinical investigation 20010701 |
| Serum concentration of androstenediol and androstenediol sulfate in patients with hyperthyroidism and hypothyroidism. | Endocrine journal 20010601 |
| Pregnenolone sulfate block of GABA(A) receptors: mechanism and involvement of a residue in the M2 region of the alpha subunit. | The Journal of physiology 20010501 |
| Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain. | Brain research 20010427 |
| Developmental changes in progesterone biosynthesis and metabolism in the quail brain. | Brain research 20010413 |
| Neurosteroid-induced enhancement of glutamate transmission in rat hippocampal slices. | Neuroscience letters 20010330 |
| Distinct effect of pregnenolone sulfate on NMDA receptor subtypes. | Neuropharmacology 20010301 |
| Allopregnanolone, pregnenolone sulfate, and epitestosterone in breast cyst fluid. | Steroids 20010101 |
| Neuroactive steroid levels in patients with generalized anxiety disorder. | The Journal of neuropsychiatry and clinical neurosciences 20010101 |
| Mitochondrial diazepam-binding inhibitor receptor complex agonists antagonize dizocilpine amnesia: putative role for allopregnanolone. | The Journal of pharmacology and experimental therapeutics 19940701 |
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