SCS-C008198

neocucurbol B

Pathway: Terpenoids Superclass: Sesquiterpenoids

Chemical Structure

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Source Information

Neocucurbitaria unguis-hominis (NA)

Kingdom Fungi Phylum Ascomycota Class Dothideomycetes Order Pleosporales Family Cucurbitariaceae Genus Neocucurbitaria Species Neocucurbitaria unguis-hominis

South China Sea · 3698 m · 115°21.569' E, 18°58.39' N

DOI: 10.1021/acs.jnatprod.2c00249 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

332.4 Da

Threshold ≤ 500

ALogP

1.94

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C20H28O4

Molecular Weight:

332.4400 Da

SMILES:

CC1=CC[C@H]2[C@]3(O[C@H]4[C@@]2(C)[C@@H](O)C[C@@]2(C)[C@H](C)CC=C3[C@@]42O)[C@H]1O

InChIKey:

                        XGZMQLSTXBDFJB-LPEYFRIRSA-N
                        
                    

InChI:

InChI=1S/C20H28O4/c1-10-5-7-12-18(4)14(21)9-17(3)11(2)6-8-13-19(12,15(10)22)24-16(18)20(13,17)23/h5,8,11-12,14-16,21-23H,6-7,9H2,1-4H3/t11-,12-,14+,15+,16+,17+,18-,19-,20-/m1/s1

Calculated Properties

ALogP:

1.939 lipophilicity

TPSA:

69.92 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (0 aromatic)

Chiral Centers:

Fsp³:

0.8000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008198

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Sesquiterpenoids

NPClassifier Class:

N/A

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 cancer cell lines SF-268, MCF-7, HepG-2, A549	> 10.0 μM	10.1021/acs.jnatprod.2c00249 Journal of Natural Products
Antibacterial	—	Escherichia coli, Staphylococcus aureus	none of the tested compounds showed antimicrobial activity.	10.1021/acs.jnatprod.2c00249 Journal of Natural Products

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