Ophiobolin C

Category	Human immunodeficiency Virus (HIV)
CAS	19022-51-6
Description	A member of the ophiobolin class of phytotoxic metabolites produced by many species of the genus bipolaris; inhibits human CCR5 binding to the envelope protein gp120 and CD4 that mediates HIV-1 entry into cells.

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Synonyms	Zizanin A
IUPAC Name	(1R,3S,4R,7S,8E,11S,12R)-4-hydroxy-1,4-dimethyl-12-[(2S)-6-methylhept-5-en-2-yl]-6-oxotricyclo[9.3.0.03,7]tetradec-8-ene-8-carbaldehyde
Molecular Weight	386.57
Molecular Formula	C25H38O3
Canonical SMILES	CC(CCC=C(C)C)C1CCC2(C1CC=C(C3C(C2)C(CC3=O)(C)O)C=O)C
InChI	InChI=1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h7,9,15,17,19-21,23,28H,6,8,10-14H2,1-5H3/b18-9-/t17-,19+,20-,21-,23+,24+,25+/m0/s1
InChIKey	PLWMYIADTRHIMY-BNFAVABNSA-N
Boiling Point	512.4°C at 760 mmHg
Melting Point	121°C
Flash Point	277.8°C
Purity	>98% by HPLC
Density	1.064 g/cm3
Solubility	Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility.
Appearance	Colorless Crystalline
Storage	Store at -20°C
Complexity	686
Exact Mass	386.28209507
Index Of Refraction	1.544
PSA	54.37000
Target	CCR; HIV
Vapor Pressure	1.21E-12mmHg at 25°C
XLogP3-AA	5.3