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496868-77-0,MFCD05861282
Catalog No.:AA00DB1V
496868-77-0 | (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid
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1mg
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5mg
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10mg
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25mg
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50mg
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  • Technical Information
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Technical Information
Catalog Number:
AA00DB1V
Chemical Name:
(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid
CAS Number:
496868-77-0
Molecular Formula:
C25H26O3
Molecular Weight:
374.4721
MDL Number:
MFCD05861282
IUPAC Name:
(E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid
InChI:
InChI=1S/C25H26O3/c26-23-7-6-21(20-4-1-16(2-5-20)3-8-24(27)28)12-22(23)25-13-17-9-18(14-25)11-19(10-17)15-25/h1-8,12,17-19,26H,9-11,13-15H2,(H,27,28)/b8-3+
InChI Key:
QAWBIEIZDDIEMW-FPYGCLRLSA-N
SMILES:
OC(=O)/C=C/c1ccc(cc1)c1ccc(c(c1)C12CC3CC(C2)CC(C1)C3)O
UNII:
W6SU73VG8H
Properties
Computed Properties
 
Complexity:
574  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
374.188g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
374.48g/mol
Monoisotopic Mass:
374.188g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
57.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.5  

Synonyms
 
adarotene 
Adarotene 
ST 1926 
ST-1926 
ST 1926 pound>>Adarotene 
SCHEMBL403527 
SCHEMBL403528 
DTXSID9040390 
NOCAS_40390 
QAWBIEIZDDIEMW-FPYGCLRLSA-N 
BCP24270 
ZINC3990465 
496868-77-0 
3419AH 
BDBM50124518 
AKOS030526823 
CS-0678 
SB17364 
(2E)-3-(3'-(A(4Sdamantan-1-yl)-4'-hydroxy-1,1'-biphenyl-4-yl)prop-2-enoic acid 
NCGC00485908-01 
HY-14808 
W-5326 
E-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamic acid 
ST1926 
(E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]cinnamic acid 
(E)-3-(3''-Adamantan-1-yl-4''-hydroxy-biphenyl-4-yl)-acrylic acid 
(2E)-3-[4'-hydroxy-3'-(tricyclo[3.3.1.13,7]dec-1-yl)biphenyl-4-yl]prop-2-enoic acid 
2-Propenoic acid, 3-(4'-hydroxy-3'-tricyclo(3.3.1.13,7)dec-1-yl(1,1'-biphenyl)-4-yl)-, (2E)- 
C25H26O3 
CID9864378 
A3143 
A11298 
C472791 
(E)-3-[4-[3-(1-adamantyl)-4-hydroxy-phenyl]phenyl]prop-2-enoic Acid 
UNII-W6SU73VG8H 
W6SU73VG8H 
CHEMBL442016 
3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid 
Adarotene [INN] 
(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid 
Literature

Title: New retinoid derivatives as back-ups of Adarotene.

Journal: Bioorganic & medicinal chemistry 20120401

Title: Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of leukemia and cancer cell lines.

Journal: Journal of medicinal chemistry 20120112

Title: Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.

Journal: Journal of medicinal chemistry 20110609

Title: Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of SRC homology 2 domain-containing protein tyrosine phosphatase-2 activity.

Journal: Journal of medicinal chemistry 20080925

Title: Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.

Journal: Bioorganic & medicinal chemistry 20070715

Title: An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and protein-tyrosine phosphatase activity.

Journal: Journal of medicinal chemistry 20070531

Title: Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways.

Journal: Molecular pharmacology 20060901

Title: Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.

Journal: Journal of medicinal chemistry 20050728

Title: Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.

Journal: Journal of medicinal chemistry 20040701

Title: ST1926, a novel and orally active retinoid-related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis.

Journal: Blood 20040101

Title: A novel atypical retinoid endowed with proapoptotic and antitumor activity.

Journal: Journal of medicinal chemistry 20030313

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