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SCS-C008231

penicimeroterpenoid C

Pathway: Polyketides | Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids
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Chemical Structure

Structure of penicimeroterpenoid C
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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

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
488.6 Da
Threshold ≤ 500
ALogP
2.75
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C27H36O8
Molecular Weight:
488.5770 Da
SMILES:
COC(=O)[C@]12[C@](C)(C(=O)[C@@]1(C)O)C(C)=C[C@H]1[C@]34CC[C@H](OC(C)=O)C(C)(C)[C@H]3[C@H](C[C@@]12C)OC4=O
InChIKey:
MCLHWXMMWGXNNX-HJTPSZCXSA-N
InChI:
InChI=1S/C27H36O8/c1-13-11-16-23(5,27(21(31)33-8)24(13,6)19(29)25(27,7)32)12-15-18-22(3,4)17(34-14(2)28)9-10-26(16,18)20(30)35-15/h11,15-18,32H,9-10,12H2,1-8H3/t15-,16+,17-,18+,23-,24-,25+,26+,27-/m0/s1
Calculated Properties
ALogP:
2.752 lipophilicity
TPSA:
116.20 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
8
Rotatable Bonds:
2
Ring Count:
5 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.7778 fraction sp³ carbon

Database Information

Compound ID:
SCS-C008231
NPClassifier Pathway:
Polyketides Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Tetraketide meroterpenoids
Glycoside:
No
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
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
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Structure enlarged