Structure Database (LMSD)

Common Name
sporogen-AO-1
Systematic Name
(3R,4R,4aR,6R)-4,4a-dimethyl-5,6-epoxy-6-(prop-1-en-2-yl)-8-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalene-3-ol-1α,3α,4βH-eremophila-9,11-diene-1,3-diol
Synonyms
LM ID
LMPR0103250004
Formula
C15H20O3
Exact Mass
Calculate m/z
248.141245
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C15 isoprenoids (sesquiterpenes) [PR0103]
Eremophilane sesquiterpenoids [PR010325]

Biological Context

Sporogen-AO 1 is a fungal metabolite originally isolated from A. oryzae that has diverse biological activities.1,2,3,4,5 It inhibits HIV-1 Tat transactivation in a cell-based assay with an IC50 value of 15.8 µM.4 Sporogen-AO 1 is cytotoxic to HeLa, KB, and NCI H187 cancer cells (IC50s = 8.3, 9, and 5.1 µM, respectively).2,5 It is active against C. albicans (MIC = 4 mM).3

This information has been provided by Cayman Chemical

References

1. Tanaka, S., Wada, K., Marumo, S., et al. Structure of sporogen-ao 1, a sporogenic substance of Aspergillus oryzae. Tetrahedron Lett. 25(51), 5907-5910 (1984).
2. Motohashi, K., Hashimoto, J., Inaba, S., et al. New sesquiterpenes, JBIR-27 and -28, isolated from a tunicate-derived fungus, Penicillium sp. SS080624SCf1. J. Antibiot. (Tokyo) 62(5), 247-250 (2009).
3. Yurchenko, A., Smetanina, O.F., Kalinovsky, A., et al. Biologically active metabolites of the facultative marine fungus Penicillium citrinum. Chem. Nat. Compd. 48(6), 996-998 (2013).
4. Jayasuriya, H., Zink, D.L., Polishook, J.D., et al. Identification of diverse microbial metabolites as potent inhibitors of HIV-1 Tat transactivation. Chem. Biodivers. 2(1), 112-122 (2005).
5. Tansakul, C., Rukachaisirikul, V., Chalothorn, T., et al. Synthesis and cytotoxicity against KB and NCI-H187 cell lines of sporogen AO-1 analogues. Phytochem. Lett. 22, 128-132 (2017).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Graphis (#71599)
Lecanoromycetes (#147547)
A new eremophilane-sesquiterpene from the cultured lichen mycobiont of Graphis sp.,
Nat Prod Res, 2020
Pubmed ID: 32573276

String Representations

InChiKey (Click to copy)
PCBDXYONDOCJPR-OANMRLRGSA-N
InChi (Click to copy)
InChI=1S/C15H20O3/c1-8(2)15-12(17)7-10-5-6-11(16)9(3)14(10,4)13(15)18-15/h7,9,11,13,16H,1,5-6H2,2-4H3/t9-,11+,13+,14+,15-/m0/s1
SMILES (Click to copy)
[C@@]12(C)[C@@H](C)[C@@H](CCC1=CC(=O)[C@@]1(O[C@H]21)C(C)=C)O

Other Databases

PubChem CID
177175
Cayman ID
29576

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 3
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 249.43
Topological Polar Surface Area 49.83
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 2.87
Molar Refractivity 69.56

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Created at
25th Jun 2020
Updated at
15th Sep 2020