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A sesterterpenoid that is (7Z)-ophiobola-7,19-diene carrying a hydroxy substituent at position 3.

Identification

IUPAC Names

(7Z)-ophiobola-7,19-dien-3-ol

Molecular Formula
C25H42O
Mass
358.60040
Monoisotopic Mass
358.32357
Charge
0
InChI
InChI=1S/C25H42O/c1-17(2)8-7-9-18(3)20-12-14-24(5)16-23-21(13-15-25(23,6)26)19(4)10-11-22(20)24/h8,10,18,20-23,26H,7,9,11-16H2,1-6H3/b19-10-/t18-,20+,21+,22-,23-,24+,25+/m0/s1
InChIKey
JNYWQVTXIGGOTC-AIKDQUDGSA-N
SMILES
C[C@@H](CCC=C(C)C)[C@H]1CC[C@]2(C)C[C@H]3[C@H](CC[C@@]3(C)O)\C(C)=C/C[C@@H]12
Synonyms

Ophiobolene

ophiobolin F

Species

synechococcus elongatus pcc 7942

MTBLS2825 

apis cerana

MTBLS379 

Europe PubMed Central results

Identification of ophiobolin F synthase by a genome mining approach: a sesterterpene synthase from Aspergillus clavatus.

Author: Chiba R, Minami A, Gomi K, Oikawa H.

Abstract: During a screening of putative diterpene synthase genes found in public databases using the Aspergillus oryzae expression system, it was found that a single transformant with the ACLA_76850 gene from A. clavatus produced a sesterterpene alcohol, ophiobolin F, and three minor sesterterpene hydrocarbons. The sesterterpene synthase has two catalytically independent domains (prenyltransferase/terpene cyclase) which are homologous to those of diterpene synthase, fusicoccadiene synthase. Coevolution of both domains and reaction mechanisms of these terpene synthases are discussed.