SCS-C008021

1-methyl-4a,12b-epoxyarisugacin M

Pathway: Terpenoids Superclass: Meroterpenoids Class: Triketide meroterpenoids

Chemical Structure

Structure of 1-methyl-4a,12b-epoxyarisugacin M

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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

Download: SDF SMILES

Source Information

Penicillium sp. SCSIO 41691 (soft coral-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA

Nansha Islands · 9°39′29.75″N, 112°59′09.84″E

DOI: 10.1021/acs.jnatprod.3c01121 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

471.5 Da

Threshold ≤ 500

ALogP

3.01

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H30O8

Molecular Weight:

471.5240 Da

SMILES:

[2H][C@@]12CC[C@@]34O[C@@](O)(OC3(C)C)[C@H](O)C[C@]4(C)[C@H]1Cc1c(cc(-c3ccc(OC)cc3)oc1=O)O2

InChIKey:

                        XJIYCQQEXIKBSD-PCTWLBCESA-N
                        
                    

InChI:

InChI=1S/C26H30O8/c1-23(2)25-10-9-18-17(24(25,3)13-21(27)26(29,33-23)34-25)11-16-20(31-18)12-19(32-22(16)28)14-5-7-15(30-4)8-6-14/h5-8,12,17-18,21,27,29H,9-11,13H2,1-4H3/t17-,18+,21+,24+,25+,26-/m0/s1/i18D

Calculated Properties

ALogP:

3.010 lipophilicity

TPSA:

107.59 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5769 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008021

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Meroterpenoids

NPClassifier Class:

Triketide meroterpenoids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.

Activity	Assay	Target / model	Result	Reference
Anti-inflammatory	IC50	nitric oxide production	Compounds 1?9 were evaluated for their inhibitory activity against LPS activated NO production in RAW 264.7 cells. The results (Table 4) showed that only 5 significantly inhibited NO production	10.1021/acs.jnatprod.3c01121 Journal of Natural Products
Antitumor	—	human lung adenocarcinoma cell line H1975	In addition, all of the tested compounds did not show obvious cytotoxicity against human lung adenocarcinoma cell line H1975 (Table 4).	10.1021/acs.jnatprod.3c01121 Journal of Natural Products

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