SCS-C001162

avermectin B1e

Pathway: Polyketides Superclass: Macrolides Class: Avermectins Glycoside

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.

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Source Information

Anthogorgia caerulea (gorgonian)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Anthogorgiidae Genus Anthogorgia Species Anthogorgia caerulea

Beibu Gulf

DOI: 10.1002/cbdv.201300265 · Chemistry & Biodiversity

Drug-likeness (Lipinski Ro5)

Molecular Weight

915.2 Da

Threshold ≤ 500

ALogP

6.40

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C51H78O14

Molecular Weight:

915.1710 Da

SMILES:

CO[C@H]1C[C@H](O[C@H]2[C@H](C)O[C@@H](O[C@@H]3/C(C)=C/C[C@@H]4C[C@@H](C[C@]5(C=C[C@H](C)[C@@H]([C@@H](C)CCC(C)C)O5)O4)OC(=O)[C@@H]4C=C(C)[C@@H](O)[C@H]5OC/C(=C\C=C\[C@@H]3C)[C@]54O)C[C@@H]2OC)O[C@@H](C)[C@@H]1O

InChIKey:

                        OEAWQZIBRYYPLE-VAAGPONXSA-N
                        
                    

InChI:

InChI=1S/C51H78O14/c1-27(2)15-16-30(5)46-31(6)19-20-50(65-46)25-37-22-36(64-50)18-17-29(4)45(28(3)13-12-14-35-26-58-48-43(52)32(7)21-38(49(54)61-37)51(35,48)55)62-42-24-40(57-11)47(34(9)60-42)63-41-23-39(56-10)44(53)33(8)59-41/h12-14,17,19-21,27-28,30-31,33-34,36-48,52-53,55H,15-16,18,22-26H2,1-11H3/b13-12+,29-17+,35-14+/t28-,30-,31-,33-,34-,36+,37-,38-,39-,40-,41-,42-,43+,44-,45-,46+,47-,48+,50+,51+/m0/s1

Calculated Properties

ALogP:

6.404 lipophilicity

TPSA:

170.06 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (0 aromatic)

Chiral Centers:

Fsp³:

0.7843 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001162

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Macrolides

NPClassifier Class:

Avermectins

Glycoside:

Yes

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
Antifouling	ED50	larval settlement of Balanus amphitrite	6.3 μg/mL	10.1002/cbdv.201300265 Chemistry & Biodiversity

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