SCS-C008184

24-hydroxyphomapyrrolidone A

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

Chemical Structure

Structure of 24-hydroxyphomapyrrolidone A

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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

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

543.7 Da

Threshold ≤ 500

ALogP

4.51

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C34H41NO5

Molecular Weight:

543.7040 Da

SMILES:

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

InChIKey:

                        ZQAAVFBSWLEBQW-BYIWXSDLSA-N
                        
                    

InChI:

InChI=1S/C34H41NO5/c1-15-10-20(14-36)12-22-24(15)31-27-25(22)18(4)28-17(3)16(2)13-34(28,5)29(27)30(37)26-23(32(38)35-33(26)39)11-19-6-8-21(40-31)9-7-19/h6-9,13,15,17,20,22-27,29,31,36H,10-12,14H2,1-5H3,(H,35,38,39)/t15-,17-,20+,22+,23-,24+,25-,26+,27-,29+,31+,34-/m0/s1

Calculated Properties

ALogP:

4.513 lipophilicity

TPSA:

92.70 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (1 aromatic)

Chiral Centers:

Fsp³:

0.6176 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008184

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	H1975 and HepG2 cell lines	> 33.0 μM	10.1021/acs.jnatprod.3c00984 Journal of Natural Products

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