SCS-C000864

verruculoid A

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

989.3 Da

Threshold ≤ 500

ALogP

7.55

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C58H72N2O10S

Molecular Weight:

989.2850 Da

SMILES:

C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23OC(=O)[C@@H](S[C@H]2CC(=O)CCC[C@@H](C)CC=C[C@H]4[C@H](O)C(=C)[C@@H](C)[C@H]5[C@H](Cc6ccccc6)NC(=O)[C@]54OC2=O)CC(=O)CCC[C@@H](C)CC=C[C@H]3[C@@H]1O

InChIKey:

                        RPNJNMTZYYPLQP-UBDWOLOGSA-N
                        
                    

InChI:

InChI=1S/C58H72N2O10S/c1-33-17-13-25-41(61)31-47(53(65)69-57-43(27-15-19-33)51(63)37(5)35(3)49(57)45(59-55(57)67)29-39-21-9-7-10-22-39)71-48-32-42(62)26-14-18-34(2)20-16-28-44-52(64)38(6)36(4)50-46(30-40-23-11-8-12-24-40)60-56(68)58(44,50)70-54(48)66/h7-12,15-16,21-24,27-28,33-36,43-52,63-64H,5-6,13-14,17-20,25-26,29-32H2,1-4H3,(H,59,67)(H,60,68)/t33-,34-,35-,36-,43+,44+,45+,46+,47+,48+,49+,50+,51-,52-,57-,58-/m1/s1

Calculated Properties

ALogP:

7.552 lipophilicity

TPSA:

185.40 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (2 aromatic)

Chiral Centers:

Fsp³:

0.5517 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000864

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
Antibacterial	MIC	Escherichia coli	2.0 μg/mL	10.1021/acs.jnatprod.1c00907 Journal of Natural Products

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