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SCS-C002049

fansecinone B

Pathway: Polyketides Superclass: Naphthalenes Class: Bisnaphthalenes | Naphthalenes and derivatives
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Chemical Structure

Structure of fansecinone 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

Aspergillus foetidus KMM 4694 (marine sediment)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus foetidus
South China Sea
DOI: 10.1080/14786419.2019.1610954  · Natural Product Research
Aspergillus niger (alga)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus niger
South China Sea
DOI: 10.3390/molecules21070941  · Molecules

Drug-likeness (Lipinski Ro5)

Molecular Weight
588.6 Da
Threshold ≤ 500
ALogP
5.19
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
11
Threshold ≤ 10
3 violations (MW, ALogP, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C32H28O11
Molecular Weight:
588.5650 Da
SMILES:
COc1cc(OC)c2c(O)c3c(c(-c4c(OC)cc5cc6oc(C)cc(=O)c6c(O)c5c4OC)c2c1)OC(C)(O)CC3=O
InChIKey:
AMDZXTMMLFPGSD-UHFFFAOYSA-N
InChI:
InChI=1S/C32H28O11/c1-13-7-17(33)25-21(42-13)9-14-8-19(39-4)27(30(41-6)22(14)28(25)35)24-16-10-15(38-3)11-20(40-5)23(16)29(36)26-18(34)12-32(2,37)43-31(24)26/h7-11,35-37H,12H2,1-6H3
Calculated Properties
ALogP:
5.194 lipophilicity
TPSA:
154.12 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
11
Rotatable Bonds:
5
Ring Count:
6 (5 aromatic)
Chiral Centers:
1
Fsp³:
0.2500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C002049
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Naphthalenes
NPClassifier Class:
Bisnaphthalenes Naphthalenes and derivatives
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 inhibition_percent 22Rv1 cells 76.61 % 10.1080/14786419.2019.1610954 Natural Product Research
Antitumor IC50 10 human tumor cell lines > 30.0 μM 10.3390/molecules21070941 Molecules
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Structure enlarged