SCS-C007870

19-S-methylgeldanamycin

Pathway: Polyketides Superclass: Macrolides Class: Ansa macrolides

Chemical Structure

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Download: SDF SMILES

Source Information

Streptomyces malaysiensis (NA)

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

South China Sea

DOI: 10.1021/acs.jnatprod.1c00297 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

606.7 Da

Threshold ≤ 500

ALogP

3.10

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C30H42N2O9S

Molecular Weight:

606.7380 Da

SMILES:

COC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=C(SC)C1=O)C2=O

InChIKey:

                        XGLOPHLGVPTCBN-WUNXPXPTSA-N
                        
                    

InChI:

InChI=1S/C30H42N2O9S/c1-15-12-19-24(34)22(28(42-8)25(35)27(19)40-7)32-29(36)16(2)10-9-11-20(38-5)26(41-30(31)37)18(4)14-17(3)23(33)21(13-15)39-6/h9-11,14-15,17,20-21,23,26,33H,12-13H2,1-8H3,(H2,31,37)(H,32,36)/b11-9-,16-10+,18-14+/t15-,17+,20+,21+,23-,26+/m1/s1

Calculated Properties

ALogP:

3.099 lipophilicity

TPSA:

163.48 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (0 aromatic)

Chiral Centers:

Fsp³:

0.5333 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007870

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Macrolides

NPClassifier Class:

Ansa macrolides

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	tested cancer cell lines	compounds 1, 4, 5, and 7 showed cytotoxicity against some or all of the five cancer cell lines with IC50 values ranging from 0.067 to 7.2 μM.	10.1021/acs.jnatprod.1c00297 Journal of Natural Products

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