Structure via PubChem · Public domain (PubChem)
bactoprenol
Sign in to saveBactoprenol also known as dolichol-11 and (isomerically vaguely) C55-isoprenyl alcohol (C55-OH) is a lipid first identified in certain species of lactobacilli. It is a hydrophobic alcohol that plays a key role in the growth of cell walls (peptidoglycan) in Gram-positive bacteria.
Chemical data
- Formula
- C55H92O
- Molecular weight
- 769.3 g/mol
- IUPAC name
- (6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-6,10,14,18,22,26,30,34,38,42-decaen-1-ol
- SMILES
- CC(CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)CCO
- InChIKey
- BNAIICFZMLQZKW-CYAIWNQHSA-N
- XLogP
- 19.9
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 768.714818
Show 4 more facts
- Commons category
- Bactoprenol
- canonical SMILES
- CC(CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)CCO
- chemical formula
- C₅₅H₉₂O
- isomeric SMILES
- CC(CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)CCO
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Occurrence
- Function
- Antibiotic significance
- See also
- References
Bactoprenol also known as dolichol-11 and (isomerically vaguely) C55-isoprenyl alcohol (C55-OH) is a lipid first identified in certain species of lactobacilli. It is a hydrophobic alcohol that plays a key role in the growth of cell walls (peptidoglycan) in Gram-positive bacteria.
The double bonds all have the Z configuration except for the three ω-terminal ones, which are biosynthetically derived from (E,E)-farnesyl diphosphate.
Excerpted from Wikipedia’s “bactoprenol” article, available under the CC BY-SA 4.0 licence.