bactoprenol

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.

In the Vinony graph

Within Vinony's link graph, bactoprenol is referenced by 192 other articles, and connects out to alcohols, antibiotic and lipid.

It is catalogued under topics including Chembox image size set, Fatty alcohols and Terpenes and terpenoids.

Its subject is documented across 13 Wikipedia language editions.

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 Å²
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)

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Encyclopedic overview

5 sections

Contents

Occurrence
Function
Antibiotic significance
See also
References

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.