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SCS-C008023

3'-demethoxyterritrem B'

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

Structure of 3'-demethoxyterritrem B'
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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. SCSIO 41691 (soft coral-derived fungus)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA
Nansha Islands  · 9°39′29.75″N, 112°59′09.84″E
DOI: 10.1021/acs.jnatprod.3c01121  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
512.6 Da
Threshold ≤ 500
ALogP
2.66
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:
C28H32O9
Molecular Weight:
512.5550 Da
SMILES:
COc1ccc(-c2cc3c(c(=O)o2)C[C@]2(O)[C@@]45CO[C@@H](CC4=O)C(C)(C)[C@]5(O)CC[C@@]2(C)O3)cc1OC
InChIKey:
GBXCFTAAYBBQRG-OVTMDPFBSA-N
InChI:
InChI=1S/C28H32O9/c1-24(2)22-12-21(29)26(14-35-22)27(24,31)9-8-25(3)28(26,32)13-16-19(37-25)11-18(36-23(16)30)15-6-7-17(33-4)20(10-15)34-5/h6-7,10-11,22,31-32H,8-9,12-14H2,1-5H3/t22-,25+,26-,27+,28+/m0/s1
Calculated Properties
ALogP:
2.658 lipophilicity
TPSA:
124.66 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
9
Rotatable Bonds:
3
Ring Count:
7 (2 aromatic)
Chiral Centers:
5
Fsp³:
0.5714 fraction sp³ carbon

Database Information

Compound ID:
SCS-C008023
NPClassifier Pathway:
Polyketides Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Triketide 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
Anti-inflammatory IC50 nitric oxide production 21.0 μM 10.1021/acs.jnatprod.3c01121 Journal of Natural Products
Antitumor — human lung adenocarcinoma cell line H1975 In addition, all of the tested compounds did not show obvious cytotoxicity against human lung adenocarcinoma cell line H1975 (Table 4). 10.1021/acs.jnatprod.3c01121 Journal of Natural Products
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Structure enlarged