SCS-C000431

secalonic acid B

Pathway: Polyketides Superclass: Xanthones | Polycyclic aromatic polyketides Class: Anthraquinones and anthrones | Methyl xanthones

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Chemical Structure

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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. SCSGAF 0023 (soft coral-derived fungus)

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

South China Sea

DOI: 10.1038/ja.2012.110 · The Journal of Antibiotics

Drug-likeness (Lipinski Ro5)

Molecular Weight

638.6 Da

Threshold ≤ 500

ALogP

1.85

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C32H30O14

Molecular Weight:

638.6000 Da

SMILES:

COC(=O)[C@@]12Oc3ccc(-c4ccc5c(c4O)C(O)=C4C(=O)C[C@H](C)[C@H](O)[C@]4(C(=O)OC)O5)c(O)c3C(O)=C1C(=O)C[C@H](C)[C@@H]2O

InChIKey:

                        NFZJAYYORNVZNI-HFEWAROQSA-N
                        
                    

InChI:

InChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,35-40H,9-10H2,1-4H3/t11-,12-,27-,28-,31+,32+/m0/s1

Calculated Properties

ALogP:

1.851 lipophilicity

TPSA:

226.58 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.3750 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000431

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Xanthones Polycyclic aromatic polyketides

NPClassifier Class:

Anthraquinones and anthrones Methyl xanthones

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
Antibacterial	MIC	S. aureus biofilm	24.4–390.5 μg/mL	10.1038/ja.2012.110 The Journal of Antibiotics
Antivirulence / Quorum sensing	inhibition	S. aureus biofilm	6.25 μg/mL	10.1038/ja.2012.110 The Journal of Antibiotics

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