SCS-C005942

lobophorin F

Pathway: Polyketides Superclass: Macrolides Class: Spirotetronate macrolides 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.

Download: SDF SMILES

Source Information

Streptomyces sp. 12A35 (bacterium)

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

South China Sea · 2134 m · 17°59.928'N, 111°36.160'E

DOI: 10.3390/md11103891 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

1011.2 Da

Threshold ≤ 500

ALogP

5.85

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:

C54H78N2O16

Molecular Weight:

1011.2160 Da

SMILES:

CC(=O)NC1C(C)OC(O[C@H]2C/C=C(\C)[C@@H]3C=C[C@@H]4[C@@H](OC5CC(OC6CC(O)C(O)C(C)O6)C(O)C(C)O5)[C@@H](C)C[C@H](C)[C@H]4[C@]3(C)C(=O)C3=C(O)[C@@]4(C[C@@H](C)C(C)=C[C@H]4/C=C/2C)OC3=O)CC1(C)[N+](=O)[O-]

InChIKey:

                        XVHUAJSFJMJCLS-SUXLUPJZSA-N
                        
                    

InChI:

InChI=1S/C54H78N2O16/c1-24-13-16-38(69-42-23-52(11,56(64)65)48(32(9)68-42)55-33(10)57)26(3)19-34-18-25(2)29(6)22-54(34)50(62)43(51(63)72-54)49(61)53(12)36(24)15-14-35-44(53)27(4)17-28(5)47(35)71-41-21-39(46(60)31(8)67-41)70-40-20-37(58)45(59)30(7)66-40/h13-15,18-19,27-32,34-42,44-48,58-60,62H,16-17,20-23H2,1-12H3,(H,55,57)/b24-13+,26-19+/t27-,28-,29+,30?,31?,32?,34-,35-,36-,37?,38-,39?,40?,41?,42?,44+,45?,46?,47-,48?,52?,53+,54-/m0/s1

Calculated Properties

ALogP:

5.846 lipophilicity

TPSA:

251.91 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (0 aromatic)

Chiral Centers:

Fsp³:

0.7593 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005942

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	Staphylococcus aureus	6.25 μg/mL	10.3390/md11103891 Marine Drugs
Antibacterial	MIC	Bacillus subtilis	50.0 μg/mL	10.3390/md11103891 Marine Drugs

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