SCS-C008022

2-hydroxy-12a-dehydroxyisoterreulactone A

Pathway: Polyketides | Terpenoids Superclass: Meroterpenoids Class: Triketide meroterpenoids

Chemical Structure

Structure of 2-hydroxy-12a-dehydroxyisoterreulactone A

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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

484.5 Da

Threshold ≤ 500

ALogP

3.24

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H32O8

Molecular Weight:

484.5450 Da

SMILES:

COc1ccc(-c2cc3c(c(=O)o2)C[C@H]2[C@@](C)(CC[C@@]4(O)C(C)(C)OC(=O)[C@H](O)C[C@]24C)O3)cc1

InChIKey:

                        NBTNOBFERZYWQS-RWCFXCBYSA-N
                        
                    

InChI:

InChI=1S/C27H32O8/c1-24(2)27(31)11-10-26(4)21(25(27,3)14-18(28)23(30)35-24)12-17-20(34-26)13-19(33-22(17)29)15-6-8-16(32-5)9-7-15/h6-9,13,18,21,28,31H,10-12,14H2,1-5H3/t18-,21-,25-,26-,27-/m1/s1

Calculated Properties

ALogP:

3.243 lipophilicity

TPSA:

115.43 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.5556 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008022

NPClassifier Pathway:

Polyketides 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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