SCS-C000629

ascomylactam B

Pathway: Alkaloids | Amino acids and Peptides Superclass: Tetramate alkaloids Class: Pyrrocidine tetramate alkaloids

Chemical Structure

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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

Didymella sp. CYSK-4 (NA)

Kingdom Fungi Phylum Ascomycota Class Dothideomycetes Order Pleosporales Family Didymellaceae Genus Didymella Species NA

South China Sea

DOI: 10.1021/acs.jnatprod.8b00918 · Journal of Natural Products

Microascus sp. (NA)

Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Microascales Family Microascaceae Genus Microascus Species Microascus sp.

Offshore Hainan Island · 18°11'N, 109°25'E

DOI: 10.1021/acs.jnatprod.3c00984 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

527.7 Da

Threshold ≤ 500

ALogP

5.40

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C34H41NO4

Molecular Weight:

527.7050 Da

SMILES:

CC1=C[C@@]2(C)C(=C(C)[C@H]3[C@@H]4C[C@H](C)C[C@H](C)[C@H]4[C@H]4Oc5ccc(cc5)C[C@@]5(O)C=C(C(=O)N5)C(=O)[C@H]2[C@@H]43)[C@H]1C

InChIKey:

                        LLDBYBFRGSYHAF-VSHZSZJPSA-N
                        
                    

InChI:

InChI=1S/C34H41NO4/c1-16-11-17(2)25-23(12-16)26-20(5)28-19(4)18(3)13-33(28,6)29-27(26)31(25)39-22-9-7-21(8-10-22)14-34(38)15-24(30(29)36)32(37)35-34/h7-10,13,15-17,19,23,25-27,29,31,38H,11-12,14H2,1-6H3,(H,35,37)/t16-,17+,19+,23-,25-,26+,27+,29-,31-,33+,34-/m1/s1

Calculated Properties

ALogP:

5.397 lipophilicity

TPSA:

75.63 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (1 aromatic)

Chiral Centers:

Fsp³:

0.5882 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000629

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Tetramate alkaloids

NPClassifier Class:

Pyrrocidine tetramate 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	IC50	human tumor cell lines	4.5–29.0 μM	10.1021/acs.jnatprod.8b00918 Journal of Natural Products
Antibacterial	MIC	seven tested bacterial pathogens	0.1–0.8 μg/mL	10.1021/acs.jnatprod.3c00984 Journal of Natural Products
Antifungal	MIC	Candida albicans	12.5–25.0 μg/mL	10.1021/acs.jnatprod.3c00984 Journal of Natural Products

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