SCS-C007422

microsporanate C

Pathway: Polyketides Superclass: Macrolides Class: Spirotetronate macrolides Glycoside

Chemical Structure

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Source Information

Micromonospora harpali (NA)

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Micromonosporales Family Micromonosporaceae Genus Micromonospora Species Micromonospora haikouensis

South China Sea · -1565 m

DOI: 10.1021/acs.jnatprod.7b00176 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

1255.4 Da

Threshold ≤ 500

ALogP

5.37

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C64H90N2O23

Molecular Weight:

1255.4150 Da

SMILES:

COC(=O)N[C@H]1[C@@H](C)O[C@@H](O[C@H]2C/C=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](O)[C@H](C)O7)[C@H](C)O6)[C@@H](OC(C)=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(CC(/C=C/C(C)=O)=C[C@H](O)[C@H]4C=C2C)C3=O)C[C@]1(C)[N+](=O)[O-]

InChIKey:

                        MIEBDRBFNCHPKK-PSKMVQGPSA-N
                        
                    

InChI:

InChI=1S/C64H90N2O23/c1-28-14-19-45(85-50-27-62(11,66(77)78)57(36(9)83-50)65-61(76)79-13)29(2)21-41-42(69)22-38(16-15-32(5)67)26-64(41)59(74)51(60(75)89-64)58(73)63(12)40(28)18-17-39-52(63)30(3)20-31(4)54(39)87-49-25-46(56(35(8)82-49)84-37(10)68)86-47-24-44(71)55(34(7)81-47)88-48-23-43(70)53(72)33(6)80-48/h14-18,21-22,30-31,33-36,39-50,52-57,69-73H,19-20,23-27H2,1-13H3,(H,65,76)/b16-15+,28-14+,29-21?,58-51?/t30-,31-,33-,34-,35-,36+,39-,40-,41+,42-,43+,44+,45-,46+,47-,48+,49-,50-,52+,53-,54-,55-,56-,57-,62-,63+,64-/m0/s1

Calculated Properties

ALogP:

5.367 lipophilicity

TPSA:

343.20 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (0 aromatic)

Chiral Centers:

Fsp³:

0.7344 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007422

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 subtilis BS01	0.016–0.5 μg/mL	10.1021/acs.jnatprod.7b00176 Journal of Natural Products
Antibacterial	MIC	Bacillus thuringiensis BT01	0.016–0.5 μg/mL	10.1021/acs.jnatprod.7b00176 Journal of Natural Products

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