SCS-C005818

penilarane E

Pathway: Terpenoids

Chemical Structure

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Download: SDF SMILES

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

Drug-likeness (Lipinski Ro5)

Molecular Weight

510.9 Da

Threshold ≤ 500

ALogP

0.30

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C24H27ClO10

Molecular Weight:

510.9230 Da

SMILES:

C[C@H]1O[C@@H]2OC(=O)[C@]3(C)C[C@@H]4[C@]5(C)[C@H](O[C@]16O[C@]65[C@]23O)[C@@H]1O[C@]12C(=CC(=O)OC2(C)C)[C@@]4(O)CCl

InChIKey:

                        FEEXCIJGFJQRMY-AOMHGWPMSA-N
                        
                    

InChI:

InChI=1S/C24H27ClO10/c1-9-23-24(35-23)19(5)11(7-18(4)15(27)31-16(30-9)22(18,24)29)20(28,8-25)10-6-12(26)32-17(2,3)21(10)14(33-21)13(19)34-23/h6,9,11,13-14,16,28-29H,7-8H2,1-5H3/t9-,11-,13-,14+,16-,18+,19-,20+,21-,22+,23+,24-/m1/s1

Calculated Properties

ALogP:

0.299 lipophilicity

TPSA:

136.58 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (0 aromatic)

Chiral Centers:

Fsp³:

0.8333 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005818

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

N/A

NPClassifier Class:

N/A

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
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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