SCS-C008188

microascone 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

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

4.06

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@@H]3C(=O)[C@@]45C(=O)N[C@@](O)(Cc6ccc(cc6)O[C@@H]6[C@H]7[C@@H](C[C@H](CO)C[C@@H]7C)[C@H]1[C@H]63)[C@H]4CC=C(C)[C@@H]25

InChIKey:

                        KLLCVNIKEFXFHV-SUIRKPMGSA-N
                        
                    

InChI:

InChI=1S/C34H41NO5/c1-16-5-10-23-33(39)14-19-6-8-21(9-7-19)40-28-25-17(2)11-20(15-36)12-22(25)24-18(3)13-32(4)27(26(24)28)30(37)34(23,29(16)32)31(38)35-33/h5-9,13,17,20,22-29,36,39H,10-12,14-15H2,1-4H3,(H,35,38)/t17-,20+,22-,23+,24-,25+,26-,27-,28+,29-,32-,33+,34+/m0/s1

Calculated Properties

ALogP:

4.059 lipophilicity

TPSA:

95.86 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (1 aromatic)

Chiral Centers:

Fsp³:

0.6471 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008188

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
Enzyme inhibition	IC50	tested PTPs (CDC25B, PTP1B, PTPSig, VHR, LAR)	> 42.0 μM	10.1021/acs.jnatprod.3c00984 Journal of Natural Products

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