SCS-C000869

deoxaphomin

Pathway: Alkaloids Superclass: Pseudoalkaloids Class: Cytochalasan alkaloids

Chemical Structure

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Source Information

Curvularia verruculosa CS-129 (deep-sea endozoic fungus)

Kingdom Fungi Phylum Ascomycota Class Dothideomycetes Order Pleosporales Family Pleosporaceae Genus Curvularia Species Curvularia verruculosa

South China Sea

DOI: 10.1021/acs.jnatprod.1c00907 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

463.6 Da

Threshold ≤ 500

ALogP

3.77

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C29H37NO4

Molecular Weight:

463.6000 Da

SMILES:

C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23C(=O)/C=C/[C@H](O)CCC[C@@H](C)C/C=C/[C@H]3[C@@H]1O

InChIKey:

                        GPCJCBIEJCXNKC-TYHYBEHESA-N
                        
                    

InChI:

InChI=1S/C29H37NO4/c1-18-9-7-13-22(31)15-16-25(32)29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1

Calculated Properties

ALogP:

3.766 lipophilicity

TPSA:

86.63 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (1 aromatic)

Chiral Centers:

Fsp³:

0.5172 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000869

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Pseudoalkaloids

NPClassifier Class:

Cytochalasan alkaloids

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	inhibition	SKMEL28 melanoma; A549 non-small cell lung cancer; B16F10 melanoma; HS683 oligodendroglioma cells	marked inhibition	10.1021/acs.jnatprod.1c00907 Journal of Natural Products

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