SCS-C000548

stachybotrylactone B

Pathway: Polyketides | Terpenoids Superclass: Meroterpenoids | Sesquiterpenoids Class: Drimane sesquiterpenoids | Spriromeroterpenoids | Tetraketide meroterpenoids

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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. (soft coral-derived fungus)

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

South China Sea

DOI: 10.1016/s1875-5364(20)30030-3 · Chinese Journal of Natural Medicines

Drug-likeness (Lipinski Ro5)

Molecular Weight

386.5 Da

Threshold ≤ 500

ALogP

3.97

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C23H30O5

Molecular Weight:

386.5000 Da

SMILES:

C[C@@H]1CC[C@H]2C(C)(C)[C@H](O)CC[C@]2(C)[C@@]12Cc1c(O)cc3c(c1O2)C(=O)OC3

InChIKey:

                        GSGCEZDYQORYOG-NIVYWPPISA-N
                        
                    

InChI:

InChI=1S/C23H30O5/c1-12-5-6-16-21(2,3)17(25)7-8-22(16,4)23(12)10-14-15(24)9-13-11-27-20(26)18(13)19(14)28-23/h9,12,16-17,24-25H,5-8,10-11H2,1-4H3/t12-,16+,17-,22+,23-/m1/s1

Calculated Properties

ALogP:

3.970 lipophilicity

TPSA:

75.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.6957 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000548

NPClassifier Pathway:

Polyketides Terpenoids

NPClassifier Superclass:

Meroterpenoids Sesquiterpenoids

NPClassifier Class:

Drimane sesquiterpenoids Spriromeroterpenoids 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
Antitumor	IC50	HL-60, K562, MOLT-4, ACHN, 786-O, OS-RC-2 cell lines	5.23 μM	10.1016/s1875-5364(20)30030-3 Chinese Journal of Natural Medicines

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