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SCS-C006073

Δ6,12-isomer of 5,6-dehydro-7-hydroxy-cytochalasin E

Pathway: Alkaloids Superclass: Pseudoalkaloids Class: Cytochalasan alkaloids
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Chemical Structure

Structure of Δ6,12-isomer of 5,6-dehydro-7-hydroxy-cytochalasin E
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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

Aspergillus sp. (coral-derived fungus)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species NA
South China Sea
DOI: 10.3390/molecules30224483  · Molecules

Drug-likeness (Lipinski Ro5)

Molecular Weight
495.6 Da
Threshold ≤ 500
ALogP
2.85
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C28H33NO7
Molecular Weight:
495.5720 Da
SMILES:
C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23OC(=O)O/C=C/C(C)(O)C(=O)[C@@H](C)C/C=C/[C@H]3[C@@H]1O
InChIKey:
OLBHIGPILGBPMF-WSSFCHPFSA-N
InChI:
InChI=1S/C28H33NO7/c1-16-9-8-12-20-23(30)18(3)17(2)22-21(15-19-10-6-5-7-11-19)29-25(32)28(20,22)36-26(33)35-14-13-27(4,34)24(16)31/h5-8,10-14,16-17,20-23,30,34H,3,9,15H2,1-2,4H3,(H,29,32)/b12-8+,14-13+/t16-,17+,20-,21-,22-,23+,27?,28+/m0/s1
Calculated Properties
ALogP:
2.849 lipophilicity
TPSA:
122.16 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
7
Rotatable Bonds:
2
Ring Count:
4 (1 aromatic)
Chiral Centers:
8
Fsp³:
0.4643 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006073
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Pseudoalkaloids
NPClassifier Class:
Cytochalasan alkaloids
Glycoside:
No
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 small cell lung cancer cell line H446; small cell lung cancer cell line H1048 0.044–1.61 μM 10.3390/molecules30224483 Molecules
Antibacterial — Alternaria alternate, Curvularia australiensis, Rhizoctonia solani, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Exiguobacterium profundum Compounds 1–10 were also tested for their antimicrobial activities [...] none of those compounds showed observable activity with 50 μg per 6 mm disk. 10.3390/molecules30224483 Molecules
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Structure enlarged