SCS-C006348

gutingimycin B

Pathway: Polyketides Superclass: Polycyclic aromatic polyketides Class: Anthraquinones and anthrones 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 · 5-10 cm

DOI: 10.3390/md19120688 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

1030.0 Da

Threshold ≤ 500

ALogP

-0.37

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C47H59N5O21

Molecular Weight:

1030.0030 Da

SMILES:

COc1c2c(c(O)c3c4c(c(C)cc13)[C@@H]1O[C@@]3(C(OC)OC)O[C@@H]1[C@@](O[C@H]1C[C@@H](O)[C@@](O)(C(C)O)[C@H](C)O1)(O4)[C@@]3(O)Cn1cnc3nc(N)[nH]c(=O)c31)C(=O)[C@@H](O)C[C@@H]2O[C@H]1C[C@@](C)(O)[C@H](OC(C)=O)[C@H](C)O1

InChIKey:

                        OFVFJTXWTHVIIB-MCJMEQTRSA-N
                        
                    

InChI:

InChI=1S/C47H59N5O21/c1-16-10-21-28(33(58)30-29(34(21)63-7)23(11-22(55)32(30)57)69-26-13-43(6,60)37(17(2)66-26)68-20(5)54)35-27(16)36-38-46(71-35,70-25-12-24(56)45(62,18(3)53)19(4)67-25)44(61,47(72-36,73-38)41(64-8)65-9)14-52-15-49-39-31(52)40(59)51-42(48)50-39/h10,15,17-19,22-26,36-38,41,53,55-56,58,60-62H,11-14H2,1-9H3,(H3,48,50,51,59)/t17-,18?,19-,22-,23-,24+,25-,26-,36-,37+,38-,43+,44-,45+,46+,47-/m0/s1

Calculated Properties

ALogP:

-0.370 lipophilicity

TPSA:

366.87 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

10 (4 aromatic)

Chiral Centers:

Fsp³:

0.6383 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006348

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Polycyclic aromatic polyketides

NPClassifier Class:

Anthraquinones and anthrones

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
Antitumor	IC50	H460 lung cancer cell line	> 1000.0 nM	10.3390/md19120688 Marine Drugs

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