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Lexacalcitol

CAS No.:
131875-08-6
Catalog Number:
AG009CCP
Molecular Formula:
C29H48O4
Molecular Weight:
460.6890
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Product Description
Catalog Number:
AG009CCP
Chemical Name:
Lexacalcitol
CAS Number:
131875-08-6
Molecular Formula:
C29H48O4
Molecular Weight:
460.6890
MDL Number:
MFCD00867078
IUPAC Name:
(1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aS)-1-[(1R)-1-(4-ethyl-4-hydroxyhexoxy)ethyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
InChI:
InChI=1S/C29H48O4/c1-6-29(32,7-2)16-9-17-33-21(4)25-13-14-26-22(10-8-15-28(25,26)5)11-12-23-18-24(30)19-27(31)20(23)3/h11-12,21,24-27,30-32H,3,6-10,13-19H2,1-2,4-5H3/b22-11+,23-12-/t21-,24-,25-,26+,27+,28-/m1/s1
InChI Key:
KLZOTDOJMRMLDX-YBBVPDDNSA-N
SMILES:
CCC(CCCO[C@@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C/1\C[C@@H](O)C[C@@H](C1=C)O)C)(CC)O
UNII:
9G3DCA3958
Properties
Complexity:
734  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
2  
Exact Mass:
460.355g/mol
Formal Charge:
0
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
460.699g/mol
Monoisotopic Mass:
460.355g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
69.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.9  
Literature
Title Journal
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Synergistic induction of gene expression during the differentiation into mature macrophage in human myeloblastic leukemia cells treated with TPA and KH1060. Leukemia research 20090601
Vitamin D-binding protein influences total circulating levels of 1,25-dihydroxyvitamin D3 but does not directly modulate the bioactive levels of the hormone in vivo. Endocrinology 20080701
Interaction among vitamin D(3) analogue KH 1060, TNF-alpha, and vitamin D receptor protein in peripheral blood mononuclear cells of inflammatory bowel disease patients. International immunopharmacology 20060701
Vitamin D receptor: ligand recognition and allosteric network. Journal of medicinal chemistry 20060223
Human cathelicidin antimicrobial peptide (CAMP) gene is a direct target of the vitamin D receptor and is strongly up-regulated in myeloid cells by 1,25-dihydroxyvitamin D3. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050701
Biochemical effects of KH 1060 and anti-TNF monoclonal antibody on human peripheral blood mononuclear cells. International immunopharmacology 20050401
Targacept active conformation search: a new method for predicting the conformation of a ligand bound to its protein target. Journal of medicinal chemistry 20041230
9-cis retinoic acid accelerates calcitriol-induced osteocalcin production and promotes degradation of both vitamin D receptor and retinoid X receptor in human osteoblastic cells. Journal of cellular biochemistry 20030815
Inhibition of MG-63 cell cycle progression by synthetic vitamin D3 analogs mediated by p27, Cdk2, cyclin E, and the retinoblastoma protein. Biochemical pharmacology 20030801
1,25-dihydroxyvitamin D3-induced apoptosis of retinoblastoma cells is associated with reciprocal changes of Bcl-2 and bax. Experimental eye research 20030701
Anti-proliferative effects of 20-epi-vitamin-D3 analogue, KH1060 in human neuroblastoma: induction of RAR-beta and p21(Cip1). Cancer letters 20030210
Involvement of diverse protein kinase C isoforms in the differentiation of ML-1 human myeloblastic leukemia cells induced by the vitamin D3 analogue KH1060 and the phorbol ester TPA. Cancer letters 20021201
Synergistic inhibitory effect of cyclosporin A and vitamin D derivatives on T-lymphocyte proliferation in active ulcerative colitis. The American journal of gastroenterology 20020301
Synergistic effect of vitamin D derivatives and retinoids on C2C12 skeletal muscle cells. IUBMB life 20020301
A combination of KH1060, a vitamin D(3) analogue, and cyclosporin prevents early graft failure and prolongs graft survival of xenogeneic islets in nonobese diabetic mice. Transplantation proceedings 20010501
Vitamin D(3) and its synthetic analogs inhibit the spontaneous in vitro immunoglobulin production by SLE-derived PBMC. Clinical immunology (Orlando, Fla.) 20010401
Suppressive effect of 1,25-dihydroxyvitamin D3 and its analogues EB 1089 and KH 1060 on T lymphocyte proliferation in active ulcerative colitis. Biochemical pharmacology 20010201
Cytotoxic effects of 1 alpha,25-dihydroxyvitamin D3 and synthetic vitamin D3 analogues on a glioma cell line. Cancer letters 19960227
Studies on two new vitamin D analogs, EB 1089 and KH 1060: effects on bone resorption and osteoclast recruitment in vitro. Bone 19951001
Properties