SCS-C005859

Gibbosolide A

Pathway: Polyketides Superclass: Macrolides

Chemical Structure

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Source Information

Amphidinium gibbosum (dinoflagellate)

Kingdom NA Phylum Alveolata Class Dinophyceae Order Amphidiniales Family Amphidiniaceae Genus Amphidinium Species Amphidinium gibbosum

South China Sea

DOI: 10.1039/d1qo01038g · Organic Chemistry Frontiers

Drug-likeness (Lipinski Ro5)

Molecular Weight

608.8 Da

Threshold ≤ 500

ALogP

3.89

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C34H56O9

Molecular Weight:

608.8130 Da

SMILES:

C/C1=C\[C@H](O)/C=C(\C)C(=O)O[C@H](C[C@@H](O)[C@H]2CC[C@@H]3O[C@@H](C)C[C@@H]3O2)C/C(C)=C/[C@H](C)C[C@H](O)[C@@H](C)C[C@@H](O)C[C@@H](O)C1

InChIKey:

                        SJFQEQRRIFFVIB-NQVFCMMTSA-N
                        
                    

InChI:

InChI=1S/C34H56O9/c1-19-9-20(2)13-29(38)22(4)14-27(37)17-26(36)11-21(3)10-25(35)15-23(5)34(40)42-28(12-19)18-30(39)31-7-8-32-33(43-31)16-24(6)41-32/h9-10,15,20,22,24-33,35-39H,7-8,11-14,16-18H2,1-6H3/b19-9+,21-10+,23-15+/t20-,22-,24-,25-,26-,27+,28-,29-,30+,31+,32-,33-/m0/s1

Calculated Properties

ALogP:

3.893 lipophilicity

TPSA:

145.91 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (0 aromatic)

Chiral Centers:

Fsp³:

0.7941 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005859

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Macrolides

NPClassifier Class:

N/A

Glycoside:

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
Receptor / Signaling modulation	inhibition_percent	human farnesoid X receptor (hFXR)	33.86 %	10.1039/d1qo01038g Organic Chemistry Frontiers
Receptor / Signaling modulation	—	human farnesoid X receptor (hFXR)	200.0 nM	10.1039/d1qo01038g Organic Chemistry Frontiers

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