SCS-C006792

lobophorin E

Pathway: Polyketides Superclass: Macrolides Class: Spirotetronate macrolides Glycoside

Chemical Structure

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Source Information

Streptomyces sp. (bacterium)

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Kitasatosporales Family Streptomycetaceae Genus Streptomyces Species NA

South China Sea · 1350 m · E 111°54.693′, N 08°56.003′

DOI: 10.1038/ja.2011.78 · The Journal of Antibiotics

Drug-likeness (Lipinski Ro5)

Molecular Weight

1171.4 Da

Threshold ≤ 500

ALogP

6.60

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:

C61H90N2O20

Molecular Weight:

1171.3850 Da

SMILES:

COC(=O)N[C@H]1[C@@H](C)O[C@@H](O[C@H]2CC=C(C)[C@@H]3C=C[C@@H]4[C@@H](O[C@H]5C[C@@H](O[C@H]6C[C@@H](O)[C@@H](O[C@@H]7C[C@@H](O)[C@@H](OC)[C@H](C)O7)[C@H](C)O6)[C@@H](O)[C@H](C)O5)[C@@H](C)C[C@H](C)[C@H]4[C@]3(C)C(O)=C3C(=O)O[C@]4(C[C@@H](C)C(C)=C[C@H]4C=C2C)C3=O)C[C@]1(C)[N+](=O)[O-]

InChIKey:

                        OARQKMNMTSJVDS-TUEPBSDPSA-N
                        
                    

InChI:

InChI=1S/C61H90N2O20/c1-27-15-18-42(79-47-26-59(11,63(71)72)54(36(10)78-47)62-58(70)74-14)29(3)21-37-20-28(2)32(6)25-61(37)56(68)48(57(69)83-61)55(67)60(12)39(27)17-16-38-49(60)30(4)19-31(5)51(38)81-46-24-43(50(66)33(7)75-46)80-44-23-41(65)53(35(9)77-44)82-45-22-40(64)52(73-13)34(8)76-45/h15-17,20-21,30-47,49-54,64-67H,18-19,22-26H2,1-14H3,(H,62,70)/t30-,31-,32+,33-,34-,35-,36+,37-,38-,39-,40+,41+,42-,43+,44-,45+,46-,47-,49+,50-,51-,52-,53-,54-,59-,60+,61-/m0/s1

Calculated Properties

ALogP:

6.601 lipophilicity

TPSA:

288.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (0 aromatic)

Chiral Centers:

Fsp³:

0.7869 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006792

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Macrolides

NPClassifier Class:

Spirotetronate macrolides

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
Antibacterial	MIC	Bacillus thuringiensis SCSIO BT01	8.0 μg ml-1	10.1038/ja.2011.78 The Journal of Antibiotics
Antibacterial	MIC	Staphylococcus aureus ATCC 29213	— Structured numeric value is not available in this record; see the primary reference.	10.1038/ja.2011.78 The Journal of Antibiotics

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