SCS-C008200

neocucurbol D

Pathway: Terpenoids Superclass: Sesquiterpenoids Class: Eremophilane 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

316.4 Da

Threshold ≤ 500

ALogP

2.97

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C20H28O3

Molecular Weight:

316.4410 Da

SMILES:

CC1=CC[C@@H]2[C@@]3(C)CC[C@]4(C)C5=C([C@@H](O)C[C@H]4C)[C@@]2(O[C@H]53)[C@H]1O

InChIKey:

                        GGTHWUGTBMEPRT-HNUUYZPBSA-N
                        
                    

InChI:

InChI=1S/C20H28O3/c1-10-5-6-13-19(4)8-7-18(3)11(2)9-12(21)14-15(18)17(19)23-20(13,14)16(10)22/h5,11-13,16-17,21-22H,6-9H2,1-4H3/t11-,12+,13-,16+,17-,18+,19-,20-/m1/s1

Calculated Properties

ALogP:

2.968 lipophilicity

TPSA:

49.69 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-C008200

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Sesquiterpenoids

NPClassifier Class:

Eremophilane sesquiterpenoids

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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