SCS-C007258

methyl ester of haterumadioxin B

Pathway: Polyketides Superclass: Linear polyketides Class: Open-chain polyketides

Chemical Structure

Structure of methyl ester of haterumadioxin B

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Source Information

Plakortis simplex (NA)

Kingdom Metazoa Phylum Porifera Class Homoscleromorpha Order Homosclerophorida Family Plakinidae Genus Plakortis Species Plakortis simplex

South China Sea

DOI: 10.1016/j.bmc.2014.07.034 · Bioorganic & Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

326.5 Da

Threshold ≤ 500

ALogP

4.97

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C19H34O4

Molecular Weight:

326.4770 Da

SMILES:

CCCC[C@H](CC)C[C@]1(CC)C=C(CC)[C@H](CC(=O)OC)OO1

InChIKey:

                        HOUYHRRILQWCPH-VDZJLULYSA-N
                        
                    

InChI:

InChI=1S/C19H34O4/c1-6-10-11-15(7-2)13-19(9-4)14-16(8-3)17(22-23-19)12-18(20)21-5/h14-15,17H,6-13H2,1-5H3/t15-,17-,19+/m0/s1

Calculated Properties

ALogP:

4.972 lipophilicity

TPSA:

44.76 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

1 (0 aromatic)

Chiral Centers:

Fsp³:

0.8421 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007258

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Linear polyketides

NPClassifier Class:

Open-chain polyketides

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
Antiparasitic	IC50	D10 (chloroquine-sensitive) and W2 (chloroquine-resistant) Plasmodium falciparum strains	The isolated endoperoxide derivatives ... have been tested for their in vitro antimalarial activity against D10 (CQ-S) and W2 (CQ-R) strains of Plasmodium falciparum. As reported in Table 3, they showed IC50 values in the low micromolar range.	10.1016/j.bmc.2014.07.034 Bioorganic & Medicinal Chemistry

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