SCS-C005320

amestolkolide B

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

Chemical Structure

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Source Information

Penicillium sp. F0836 (soft coral-derived fungus)

Original source name: Penicillium sp. (strain F0836)

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

South China Sea · -670m · 115.1896°E, 20.0887°N

DOI: 10.1021/acs.jmedchem.5c03055 · Journal of Medicinal Chemistry

Talaromyces amestolkiae (mangrove plant)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Trichocomaceae Genus Talaromyces Species Talaromyces amestolkiae

Zhanjiang Mangrove Nature Reserve

DOI: 10.1016/j.phytochem.2017.11.011 · Phytochemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

442.5 Da

Threshold ≤ 500

ALogP

1.66

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H26O8

Molecular Weight:

442.4640 Da

SMILES:

C[C@H]1O[C@@H]2OC(=O)[C@]3(C)C[C@@H]4[C@](C)(C(=O)C=C5C(=CC(=O)OC5(C)C)[C@@]45CO5)[C@H](C1=O)[C@H]23

InChIKey:

                        PCBBMDQLBUYDDZ-NBYUEMIISA-N
                        
                    

InChI:

InChI=1S/C24H26O8/c1-10-18(27)16-17-19(30-10)31-20(28)22(17,4)8-13-23(16,5)14(25)6-11-12(24(13)9-29-24)7-15(26)32-21(11,2)3/h6-7,10,13,16-17,19H,8-9H2,1-5H3/t10-,13-,16+,17-,19-,22-,23-,24+/m1/s1

Calculated Properties

ALogP:

1.662 lipophilicity

TPSA:

108.50 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (0 aromatic)

Chiral Centers:

Fsp³:

0.6667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005320

NPClassifier Pathway:

Polyketides Terpenoids

NPClassifier Superclass:

Meroterpenoids

NPClassifier Class:

Tetraketide meroterpenoids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD30961

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
Receptor / Signaling modulation	inhibition	TGF-β1/Smad signaling; HSF1/AMPK metabolic axis	10.0 μM	10.1021/acs.jmedchem.5c03055 Journal of Medicinal Chemistry

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