SCS-C008229
penicimeroterpenoid A
Pathway: Polyketides | Terpenoids
Superclass: Meroterpenoids
Class: Tetraketide meroterpenoids
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.
Source Information
Penicillium sp.
(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.0c02160
· Organic Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
516.6 Da
Threshold ≤ 500
ALogP
2.32
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C28H36O9
Molecular Weight:
516.5870 Da
SMILES:
COC(=O)[C@@]12C(=O)[C@](C)(O)C(=O)[C@@H](C(C)=C1C)[C@H]1[C@]34CC[C@H](OC(C)=O)C(C)(C)[C@H]3[C@@H](C[C@]12C)OC4=O
InChIKey:
NKJCLWNIOFTRBB-SNTLOJMCSA-N
InChI:
InChI=1S/C28H36O9/c1-12-13(2)28(23(33)35-8)21(31)26(7,34)20(30)17(12)19-25(28,6)11-15-18-24(4,5)16(36-14(3)29)9-10-27(18,19)22(32)37-15/h15-19,34H,9-11H2,1-8H3/t15-,16+,17+,18-,19-,25-,26-,27+,28+/m1/s1
Calculated Properties
ALogP:
2.321 lipophilicity
TPSA:
133.27 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
9
Rotatable Bonds:
2
Ring Count:
6
(0 aromatic)
Chiral Centers:
9
Fsp³:
0.7500 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008229
NPClassifier Pathway:
Polyketides
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Tetraketide meroterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 |
|---|---|---|---|---|
| Enzyme inhibition | inhibition ratio | cathepsin L, xanthine oxidase (XO), human leukocyte elastase (HLE), trypsin | 10.0–50.0 % | 10.1021/acs.orglett.0c02160 Organic Letters |
| Enzyme inhibition | inhibition ratio | seven protein tyrosine phosphatases (CDC25B, TCPTP, SHP1, MEG2, SHP2, PTP1B, CD45) | -20.0 % | 10.1021/acs.orglett.0c02160 Organic Letters |
| Enzyme inhibition | IC50 | CDC25B | ~ 20.0 μM | 10.1021/acs.orglett.0c02160 Organic Letters |
| Enzyme inhibition | inhibition | CDC25B, SHP1 | 1?3 displayed moderate inhibitory activity toward CDC25B and SHP1 | 10.1021/acs.orglett.0c02160 Organic Letters |