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  3. (E)-2-(7,11-dimethyl-3-methylenedodeca-6,10-dien-1-yn-1-yl)benzene-1,4-diol (pestalotioquinol E)

SCS-C007964

(E)-2-(7,11-dimethyl-3-methylenedodeca-6,10-dien-1-yn-1-yl)benzene-1,4-diol (pestalotioquinol E)

Pathway: Terpenoids Superclass: Meroterpenoids Class: Merosesquiterpenoids
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Chemical Structure

Structure of (E)-2-(7,11-dimethyl-3-methylenedodeca-6,10-dien-1-yn-1-yl)benzene-1,4-diol (pestalotioquinol E)
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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

Pestalotiopsis neglecta SCSIO 41403 (SCSIO41403)
Original source name: Pestalotiopsis neglecta SCSIO41403
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Amphisphaeriales Family Sporocadaceae Genus Pestalotiopsis Species Pestalotiopsis neglecta
South China Sea
DOI: 10.1021/acs.jnatprod.0c00050  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
310.4 Da
Threshold ≤ 500
ALogP
5.48
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C21H26O2
Molecular Weight:
310.4370 Da
SMILES:
C=C(C#Cc1cc(O)ccc1O)CC/C=C(\C)CCC=C(C)C
InChIKey:
WXUBHLFYGYMBEU-RQZCQDPDSA-N
InChI:
InChI=1S/C21H26O2/c1-16(2)7-5-8-17(3)9-6-10-18(4)11-12-19-15-20(22)13-14-21(19)23/h7,9,13-15,22-23H,4-6,8,10H2,1-3H3/b17-9+
Calculated Properties
ALogP:
5.478 lipophilicity
TPSA:
40.46 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
2
Rotatable Bonds:
6
Ring Count:
1 (1 aromatic)
Chiral Centers:
0
Fsp³:
0.3333 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007964
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Merosesquiterpenoids
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
Antitumor IC50 ACHN, OS-RC-2, 786-O, HL-60, K-562, MOLT-4 cell lines > 50.0 μM 10.1021/acs.jnatprod.0c00050 Journal of Natural Products
Antiviral — Dengue virus — Structured numeric value is not available in this record; see the primary reference. 10.1021/acs.jnatprod.0c00050 Journal of Natural Products
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Structure enlarged