SCS-C007374

gibbosterol A

Pathway: Terpenoids Superclass: Steroids Class: Stigmastane steroids

Chemical Structure

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Download: SDF SMILES

Source Information

Amphidinium gibbosum (dinoflagellate)

Original source name: Amphidinium gibbosum (A. gibbosum)

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

South China Sea

DOI: 10.1021/acs.orglett.0c04075 · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

510.7 Da

Threshold ≤ 500

ALogP

3.14

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C29H50O7

Molecular Weight:

510.7120 Da

SMILES:

CC(C)/C(=C\CO)[C@@H](O)C[C@@H](C)[C@H]1CC[C@H]2C(=O)CC[C@H](O)C[C@@H](O)CC[C@@](C)(O)[C@@H]3O[C@H]3C[C@]12C

InChIKey:

                        FIUZEAOPYHVKTA-JISFWASHSA-N
                        
                    

InChI:

InChI=1S/C29H50O7/c1-17(2)21(11-13-30)25(34)14-18(3)22-7-8-23-24(33)9-6-19(31)15-20(32)10-12-29(5,35)27-26(36-27)16-28(22,23)4/h11,17-20,22-23,25-27,30-32,34-35H,6-10,12-16H2,1-5H3/b21-11+/t18-,19+,20+,22-,23+,25+,26+,27-,28-,29-/m1/s1

Calculated Properties

ALogP:

3.144 lipophilicity

TPSA:

130.75 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (0 aromatic)

Chiral Centers:

Fsp³:

0.8966 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007374

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Steroids

NPClassifier Class:

Stigmastane steroids

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	agonistic activity	human pregnane-X-receptor (PXR)	Compound 1 exhibited significant agonistic effects in a dose-dependent manner within the concentration range of 100.0 nm to 10.0 μM	10.1021/acs.orglett.0c04075 Organic Letters

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