Structure Database (LMSD)

Common Name
Adipostatin A
Systematic Name
5-pentadecylbenzene-1,3-diol
Synonyms
  • 5-n-pentadecylresorcinol
  • cardol
  • 5-pentadecylresorcinol
LM ID
LMPK15030012
Formula
C21H36O2
Exact Mass
Calculate m/z
320.27153
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Alkyl resorcinols and derivatives [PK1503]

Biological Context

Adipostatin A is an inhibitor of glycerol-3-phosphate dehydrogenase (GPDH; IC50 = 4.1 µM).1 It prevents triglyceride accumulation in 3T3-L1 cells when applied at 5-7.5 µM.1 Adipostatin A is cytotoxic against fibroblast carcinoma KB cell lines with an IC50 value of 10.6 µM.2

This information has been provided by Cayman Chemical

References

1. Tsuge, N., Mizokami, M., Imai, S., et al. Adipostatins A and B, new inhibitors of glycerol-3-phosphate dehydrogenase. J. Antibiot. (Tokyo) 45(6), 886-891 (1992).
2. Tanaka, A., Arai, Y., Kim, S.-N., et al. Synthesis and biological evaluation of bilobol and adipostatin A. J. Asian Nat. Prod. Res. 13(4), 290-296 (2011).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Anacardium occidentale (#171929)
Magnoliopsida (#3398)
Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil,
J. Agric. Food Chem., 1991
Streptomyces sp. (#1931)
Actinomycetes (#1760)
Adipostatins A-D from Streptomyces sp. 4875 inhibiting Brugia malayi asparaginyl-tRNA synthetase and killing adult Brugia malayi parasites.,
J Antibiot (Tokyo), 2015
Pubmed ID: 25735843

String Representations

InChiKey (Click to copy)
KVVSCMOUFCNCGX-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C21H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h16-18,22-23H,2-15H2,1H3
SMILES (Click to copy)
C1(O)C=C(CCCCCCCCCCCCCCC)C=C(O)C=1

Other Databases

Wikipedia
Adipostatin_A
KEGG ID
C10809
HMDB ID
HMDB0031009
CHEBI ID
2120
PubChem CID
76617
Cayman ID
22163

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 1
Rotatable Bonds 14
Van der Waals Molecular Volume 358.26
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 6.73
Molar Refractivity 99.17

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Created at
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Updated at
2nd Aug 2021