N-(7-nitrobenz-2-oxa-1,3-diazole)-23,24-dinor-5-cholen-22-amine-3beta-ol
Basic information
- CAS
78949-95-8- Standard SMILES
C[C@H](CNc1ccc([N+](=O)[O-])c2nonc12)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
DLWLXTLRGQWGPC-XIWKFBMMSA-N- Molecular formula
- C28H38N4O4
- Average molar mass
- 494.6 g/mol
- Monoisotopic mass
- 494.28930571
Names & identifiers
- Preferred name
- N-(7-nitrobenz-2-oxa-1,3-diazole)-23,24-dinor-5-cholen-22-amine-3beta-ol
- IUPAC
- (3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S)-1-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- English name
- 22-NBD cholesterol
- Molecular formula
- C28H38N4O4
- Molecular weight
- 494.63
Names & synonyms
78949-95-8Nbd-dcaPregn-5-en-3-ol, 20-methyl-21-((7-nitro-4-benzofurazanyl)amino)-, (3beta,20S)-N-(7-Nitrobenz-2-oxa-1,3-diazole)-23,24-dinor-5-cholen-22-amine-3beta-olRefChem:162280Fluoresterol(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S)-1-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol(3beta,20S)-20-Methyl-21-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]pregn-5-en-3-olorb2283213SCHEMBL29420066C28H38N4O4MFCD00467337
Show more names
NBD-cholesterolNBD cholesterol, 90%(3β,20S)-20-Methyl-21-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]pregn-5-en-3-olPregn-5-en-3-ol, 20-methyl-21-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-, (3β,20S)-NBD cholesterol [22-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)aMino)-23,24-bisnor-5-cholen-3b-ol]
AS-79010PD131251CS-0031852T85045(3|_,20S)-20-Methyl-21-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]pregn-5-en-3-ol(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(1S)-1-methyl-2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Properties
Computed structural properties
- XLogP
- 6.4
- Topological polar surface area
- 117 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 893
Physicochemical properties
- Boiling point
- 650.5 · 650.5±65.0 °C(Predicted)
- Density
- 1.27 · 1.27±0.1 g/cm3(Predicted)
- storage temp.
- -10 to · -10 to -25°C
- solubility
- 1 mg/ml · Methanol: 1 mg/ml
- form
- A solid
- pka
- 15.03 · 15.03±0.70(Predicted)
- color
- Yellow to dark orange
- InChIKey
- DLWLXTLRGQWGPC-XIWKFBMMSA-N
- SMILES
- C[C@]12[C@]([H])([C@]3([C@@]([H])([C@]4(C)C(C[C@@H](O)CC4)=CC3)CC2)[H])CC[C@@]1([C@@H](CNC(C5=NON=C56)=CC=C6[N+]([O-])=O)C)[H]
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 21 · NA.21
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
Description22-NBD cholesterol is a fluorescent analog of cholesterol that contains a fluorescent nitrobenzoxadiazole (NBD) group. It has been used in a variety of in vitro and in vivo applications, including analysis of steroid uptake and esterification, intracellular localization and targeting, and metabolism in mammalian and bacterial cells, and intestinal absorption of cholesterol in hamsters. 22-NBD cholesterol displays excitation/emission maxima of 472/540 nm, respectively, when incorporated into 1,2-dimyristoyl-sn-glycero-3-PC (DMPC; ) vesicles. The emission maximum of 22-NBD cholesterol is solvent-dependent and increases as solvent polarity increases.
UsesFluoresterol is a fluorescently labeled cholesterol analog that can be used as a fluorescent probe to study the behavior and metabolism of cholesterol in cells, including lipid uptake and esterification analysis, intracellular localization and targeting, and lipid metabolism in mammalian and bacterial cells. Fluoresterol has an excitation maximum at 472 nm and an emission maximum at 540 nm. Fluoresterol is expected to be useful in the study of metabolic diseases[1][2].
Related reactions
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Compound notes
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