FR 65814

FR 65814

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Category Antibiotics
Catalog number BBF-03551
CAS 103470-60-6
Molecular Weight 268.35
Molecular Formula C15H24O4

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FR 65814 is originally isolated from Penicillum jensenii F-2883. It has a strong immunosuppressive effect, and the IC50 of inhibiting mixed lymphocyte reaction (MLR) in mice is 34 nmol/L.


Synonyms 4-(2-Methyl-3-(3-methyl-2-butenyl)oxiranyl)-1-oxaspiro(2.5)octane-5,6-diol
IUPAC Name (3R,4S,5S,6S)-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octane-5,6-diol
Canonical SMILES CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)O)O)C
InChI InChI=1S/C15H24O4/c1-9(2)4-5-11-14(3,19-11)13-12(17)10(16)6-7-15(13)8-18-15/h4,10-13,16-17H,5-8H2,1-3H3/t10-,11+,12+,13+,14-,15-/m0/s1


Appearance Colorless Sheet Cystal
Boiling Point 401.2°C at 760 mmHg
Melting Point 46-47°C
Density 1.2 g/cm3

Reference Reading

1. FR65814, a novel immunosuppressant isolated from a Penicillium strain. Taxonomy, fermentation, isolation, physico-chemical and biological characteristics and structure assignment
H Hatanaka, T Kino, M Hashimoto, Y Tsurumi, A Kuroda, H Tanaka, T Goto, M Okuhara J Antibiot (Tokyo). 1988 Aug;41(8):999-1008. doi: 10.7164/antibiotics.41.999.
FR65814, a novel immunosuppressant, was isolated from the cultured broth of Penicillium jensenii F-2883. The structure was assigned to be 5,6-dihydroxy-4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-oxaspiro++ +[2,5]octane by spectroscopic analyses. The compound suppressed the immune response at low concentration. In addition, a structually related component fumagillol, a known carcinolytic agent, was also isolated and found to show immunosuppressive activity.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40

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