SCS-C007924

dfpenicimeroterpenoid A

Pathway: Terpenoids Superclass: Triterpenoids

Chemical Structure

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Source Information

Penicillium sp. DF71 (soft coral-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA

South China Sea

DOI: 10.1021/acs.orglett.6c01506 · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

432.6 Da

Threshold ≤ 500

ALogP

2.80

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C25H36O6

Molecular Weight:

432.5570 Da

SMILES:

COC(=O)[C@]12C(=O)[C@]3(C)O[C@]1(C)[C@@]3(C)C=C1[C@]3(CO)CC[C@@H](O)C(C)(C)[C@H]3CC[C@@]12C

InChIKey:

                        DTLKOCOIXODJEX-ANZNHWSDSA-N
                        
                    

InChI:

InChI=1S/C25H36O6/c1-19(2)14-8-10-20(3)15(24(14,13-26)11-9-16(19)27)12-21(4)22(5)17(28)25(20,18(29)30-7)23(21,6)31-22/h12,14,16,26-27H,8-11,13H2,1-7H3/t14-,16-,20+,21+,22+,23-,24+,25+/m1/s1

Calculated Properties

ALogP:

2.798 lipophilicity

TPSA:

93.06 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (0 aromatic)

Chiral Centers:

Fsp³:

0.8400 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007924

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Triterpenoids

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
Angiogenesis modulation	—	intersegmental vessels	Preliminary assessment at 20 μM in transgenic zebrafish Tg(vegfr2:GFP) showed varying levels of angiogenesis activity; compound 2 exhibited significant pro-angiogenic effects, compounds 7 and 9 marginal activity.	10.1021/acs.orglett.6c01506 Organic Letters

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