Adipostatin B

Adipostatin B

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Category Antibiotics
Catalog number BBF-00039
CAS 144284-17-3
Molecular Weight 320.51
Molecular Formula C21H36O2

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Description

Adipostatin is a glycerol-3-phosphate dehydrogenase inhibitor produced in Streptornyces cyaneus 2299-SVI. Adipostatin B is an inhibitor of glycerol-3-phosphate dehydrogenase.

Specification

Synonyms 5-Isopentadecylresorcinol; 5-n-isopentadecylresorcinol
IUPAC Name 5-(13-methyltetradecyl)benzene-1,3-diol
Canonical SMILES CC(C)CCCCCCCCCCCCC1=CC(=CC(=C1)O)O
InChI InChI=1S/C21H36O2/c1-18(2)13-11-9-7-5-3-4-6-8-10-12-14-19-15-20(22)17-21(23)16-19/h15-18,22-23H,3-14H2,1-2H3
InChI Key AYZBMIJCGJIGNK-UHFFFAOYSA-N

Properties

Appearance White Powder
Boiling Point 448.1°C at 760 mmHg
Melting Point 90-91°C
Density 0.959 g/cm3

Reference Reading

1. Adipostatins A and B, new inhibitors of glycerol-3-phosphate dehydrogenase
N Tsuge, M Mizokami, S Imai, A Shimazu, H Seto J Antibiot (Tokyo). 1992 Jun;45(6):886-91. doi: 10.7164/antibiotics.45.886.
As a result of screening for inhibitors of glycerol-3-phosphate dehydrogenase, which may be effective to prevent corpulence, we isolated two inhibitors named adipostatin A and adipostatin B from the culture broth of Streptomyces cyaneus 2299-SV1. Their structures have been established to be 5-n-pentadecylresorcinol and 5-isopentadecylresorcinol, respectively. Adipostatin A and adipostatin B inhibited glycerol-3-phosphate dehydrogenase at the IC50 values of 4.1 microM and 4.5 microM, respectively. These compounds prevented triglyceride accumulation in 3T3-L1 cells at a concentration of the microM level.

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