SCS-C005815

penilarane B

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

Chemical Structure

Loading 3D structure...

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. 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

478.9 Da

Threshold ≤ 500

ALogP

1.88

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H27ClO8

Molecular Weight:

478.9250 Da

SMILES:

C[C@H]1O[C@@H]2OC(=O)[C@]3(C)C[C@@H]4[C@@]5(C)C(=C1O[C@H]5C=C1C(=CC(=O)OC1(C)C)[C@@]4(O)CCl)[C@]23O

InChIKey:

                        LQPYWJOQEBDZSC-WBTZUOPNSA-N
                        
                    

InChI:

InChI=1S/C24H27ClO8/c1-10-16-17-22(5)13(8-21(4)18(27)32-19(30-10)24(17,21)29)23(28,9-25)12-7-15(26)33-20(2,3)11(12)6-14(22)31-16/h6-7,10,13-14,19,28-29H,8-9H2,1-5H3/t10-,13-,14+,19-,21+,22-,23+,24+/m1/s1

Calculated Properties

ALogP:

1.876 lipophilicity

TPSA:

111.52 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-C005815

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

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	10.0 μM	10.1021/acs.jmedchem.5c03055 Journal of Medicinal Chemistry
Antifibrotic / Organ protection	IC50	HSF1/AMPK metabolic axis	1.8 μM	10.1021/acs.jmedchem.5c03055 Journal of Medicinal Chemistry

Back to Compounds