SCS-C007885

kendomycin D

Pathway: Polyketides Superclass: Macrolides Class: Ansa 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

Verrucosispora sp. (NA)

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Micromonosporales Family Micromonosporaceae Genus Verrucosispora Species NA

South China Sea · 2500 m

DOI: 10.1021/acs.jnatprod.9b00654 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

633.8 Da

Threshold ≤ 500

ALogP

4.39

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C33H47NO9S

Molecular Weight:

633.8040 Da

SMILES:

CC(=O)N[C@H](CSC1=C2C3=CC(=O)C(O)=C2[C@@H]2O[C@H](CC[C@H](C)/C=C(\C)C[C@@H](C)C[C@H](C)[C@]1(O)O3)[C@H](C)[C@H](O)[C@H]2C)C(=O)O

InChIKey:

                        GZDOKJSHAXCZQL-XSZJVKIISA-N
                        
                    

InChI:

InChI=1S/C33H47NO9S/c1-15-8-9-24-19(5)28(37)20(6)30(42-24)27-26-25(13-23(36)29(27)38)43-33(41,18(4)12-17(3)11-16(2)10-15)31(26)44-14-22(32(39)40)34-21(7)35/h10,13,15,17-20,22,24,28,30,37-38,41H,8-9,11-12,14H2,1-7H3,(H,34,35)(H,39,40)/b16-10+/t15-,17+,18-,19-,20+,22+,24+,28-,30+,33-/m0/s1

Calculated Properties

ALogP:

4.390 lipophilicity

TPSA:

162.62 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.6667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007885

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Macrolides

NPClassifier Class:

Ansa 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	Six Gram-positive bacteria (S. aureus ATCC 29213, S. aureus 745524, MRSA shhs-A1, E. faecalis ATCC 29212, B. subtilis BS01, B. thuringiensis BT01)	0.5–8.0 μg/mL	10.1021/acs.jnatprod.9b00654 Journal of Natural Products
Antitumor	IC50	Six human tumor cell lines (MGC803, A549, HeLa, HepG2, MCF-7, RKO) and two nonmalignant cell lines (L02, HUVEC-12)	2.2–44.0 μM	10.1021/acs.jnatprod.9b00654 Journal of Natural Products

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