(23R)-1alpha-hydroxy-25,27-didehydrovitamin D3 26,23-lactone
Basic information
- CAS
173388-21-1- Standard SMILES
C=C1C[C@@H](C[C@@H](C)[C@H]2CC[C@H]3/C(=C/C=C4/C[C@@H](O)C[C@H](O)C4=C)CCC[C@]23C)OC1=O- InChIKey
SAODSJHDCZTVAT-JXJLEVNFSA-N- Molecular formula
- C27H38O4
- Average molar mass
- 426.6 g/mol
- Monoisotopic mass
- 426.27700969
Overview
(23R)-1alpha-hydroxy-25,27-didehydrovitamin D3 26,23-lactone is a vitamin D.
Names & identifiers
- Preferred name
- (23R)-1alpha-hydroxy-25,27-didehydrovitamin D3 26,23-lactone
- IUPAC
- (5R)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylideneoxolan-2-one
- English name
- TEI-9647 enantiomer
- Molecular formula
- C27H38O4
- Molecular weight
- 426.59
Names & synonyms
173388-21-1(23R)-1alpha-hydroxy-25,27-didehydrovitamin D3 26,23-lactoneTEI 9648CHEMBL386412(5R)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylideneoxolan-2-one(5Z,7E)-(1S,3R,23R)-1,3-dihydroxy-9,10-seco-5,7,10(19),25(27)-cholestatetraeno-26,23-lactone9,10-Secocholesta-5,7,10(19),25(27)-tetraen-26-oic acid, 1,3,23-trihydroxy-, gamma-lactone, (1alpha,3beta,5Z,7E,23R)-orb1693598CHEBI:197108BDBM50411164HY-12398ALMST03020600
Show more names
TEI-9648TEI-9647 enantiomer2(3H)-Furanone, 5-[(2R)-2-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-7a-methyl-1H-inden-1-yl]propyl]dihydro-3-methylene-, (5R)-
MFCD12912576AKOS040755358DA-78296MS-27531CS-0147915G13811T36593(5R)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylene-cyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylene-tetrahydrofuran-2-one
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 821
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D3 and derivatives [ST0302]
Physicochemical properties
- Boiling point
- 618.5 · 618.5±55.0 °C(Predicted)
- Density
- 1.14 · 1.14±0.1 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light, stored under nitrogen
- pka
- 14.43 · 14.43±0.40(Predicted)
- form
- Solid
- color
- Off-white to yellow
Chemistry & industry
Applications
UsesTEI-9648, a Vitamin D3 Lactone analogue, is a potent and specific vitamin D receptor (VDR) antagonist. TEI-9648 inhibits VDR/VDRE-mediated genomic actions of 1α,25(OH)2D3. TEI-9648 also inhibits HL-60 cell differentiation induced by of 1α,25(OH)2D3. TEI-9648 has the potential for bone metabolism research[1][2].
Related reactions
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Compound notes
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