Home Other Building Blocks 516-72-3
516-72-3,MFCD16661190
Catalog No.:AA00DDBT

516-72-3 | (8S,9S,10R,13S,14S,17S)-17-((R)-2-Hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
98%
in stock  
$22.00   $15.00
- +
5mg
98%
in stock  
$66.00   $47.00
- +
10mg
98%
in stock  
$114.00   $80.00
- +
50mg
98%
in stock  
$348.00   $244.00
- +
100mg
98%
in stock  
$592.00   $415.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00DDBT
Chemical Name:
(8S,9S,10R,13S,14S,17S)-17-((R)-2-Hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number:
516-72-3
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
MDL Number:
MFCD16661190
SMILES:
CC(CCC[C@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CCC(C2)O)(O)C)C
Properties
Properties
 
Form:
Solid  
MP:
136-137°C  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
638  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
6.9  

Downstream Synthesis Route

[1]JournaloftheChemicalSociety,1956,p.4675

[1]JournaloftheChemicalSociety,1956,p.4675

[1]JournalofOrganicChemistry,1970,vol.35,p.2627-2632

[2]Bioorganicandmedicinalchemistryletters,2012,vol.22,p.5893-5897,5

[1]TetrahedronLetters,1986,vol.27,p.3369-3372

[1]TetrahedronLetters,1986,vol.27,p.3369-3372

Literature

Title: Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships.

Journal: Chemico-biological interactions 20150605

Title: Oxysterols are allosteric activators of the oncoprotein Smoothened.

Journal: Nature chemical biology 20120201

Title: Steroidogenic factor-1 (SF-1)-driven differentiation of murine embryonic stem (ES) cells into a gonadal lineage.

Journal: Endocrinology 20110701

Title: Modulators of the hedgehog signaling pathway.

Journal: Bioorganic & medicinal chemistry 20100915

Title: Enhancement of the ALP activity of C3H10T1/2 cells by the combination of an oxysterol and apatite.

Journal: Biomedical materials (Bristol, England) 20100801

Title: Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20100401

Title: 20(S)-hydroxycholesterol inhibits PPARgamma expression and adipogenic differentiation of bone marrow stromal cells through a hedgehog-dependent mechanism.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20071101

Title: Patched1 regulates hedgehog signaling at the primary cilium.

Journal: Science (New York, N.Y.) 20070720

Title: Osteogenic oxysterols inhibit the adverse effects of oxidative stress on osteogenic differentiation of marrow stromal cells.

Journal: Journal of cellular biochemistry 20050815

Title: Novel signaling stimulated by arsenite increases cholesterol metabolism through increases in unphosphorylated steroidogenic acute regulatory (StAR) protein.

Journal: Molecular and cellular endocrinology 20050227

Title: Changes in Nuclear Receptor and Vitellogenin Gene Expression in Response to Steroids and Heavy Metal in Caenorhabditis elegans.

Journal: Integrative and comparative biology 20050101

Title: Sterol-derived hormone(s) controls entry into diapause in Caenorhabditis elegans by consecutive activation of DAF-12 and DAF-16.

Journal: PLoS biology 20041001

Title: Molten globule structure and steroidogenic activity of N-218 MLN64 in human placental mitochondria.

Journal: Endocrinology 20040401

Title: Suppression of steroidogenesis and activator protein-1 transcription factor activity in rat adrenals by vitamin E deficiency-induced chronic oxidative stress.

Journal: The Journal of nutritional biochemistry 20040401

Title: Oxysterols suppress constitutive fibrinogen expression.

Journal: Thrombosis and haemostasis 20030701

Title: The detection of 20S-hydroxycholesterol in extracts of rat brains and human placenta by a gas chromatograph/mass spectrometry technique.

Journal: The Journal of steroid biochemistry and molecular biology 20030501

Title: Nonionic micellar liquid chromatography coupled to immobilized enzyme reactors.

Journal: Journal of chromatography. A 20010720

Title: Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.

Journal: Journal of medicinal chemistry 20010315

Title: The oxidation of cholesterol in the yolk of selective traditional Chinese egg products.

Journal: Poultry science 20010301

Title: Oxysterol 7 alpha-hydroxylase activity by cholesterol 7 alpha-hydroxylase (CYP7A).

Journal: The Journal of biological chemistry 20001103

Title: Nachtergaele S, et al. Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat Chem Biol. 2012 Jan 8;8(2):211-20.

Title: Nedelcu D, et al, Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling. Nat Chem Biol. 2013 Sep;9(9):557-64.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:516-72-3 Molecular Formula|516-72-3 MDL|516-72-3 SMILES|516-72-3 (8S,9S,10R,13S,14S,17S)-17-((R)-2-Hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol