SCS-C006202

22-acetyl isocyclocitrinol A

Pathway: Shikimates and Phenylpropanoids

Chemical Structure

Structure of 22-acetyl isocyclocitrinol A

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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. (soft coral-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA

South China Sea

DOI: 10.3390/md17070398 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

378.5 Da

Threshold ≤ 500

ALogP

5.40

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C24H26O4

Molecular Weight:

378.4680 Da

SMILES:

Cc1c2c(c3oc4cc(=O)c(C)c5c-4c(c3c1O)C[C@H](C)[C@H]5C)O[C@H](C)[C@H]2C

InChIKey:

                        ZVTQIUFFWRNXGO-ICUOPCATSA-N
                        
                    

InChI:

InChI=1S/C24H26O4/c1-9-7-15-20-17(8-16(25)12(4)18(20)10(9)2)28-24-21(15)22(26)13(5)19-11(3)14(6)27-23(19)24/h8-11,14,26H,7H2,1-6H3/t9-,10+,11+,14+/m0/s1

Calculated Properties

ALogP:

5.400 lipophilicity

TPSA:

59.67 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.4583 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006202

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

N/A

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
Antibacterial	inhibition zone	Staphylococcus aureus	7.0 mm	10.3390/md17070398 Marine Drugs
Antibacterial	minimum inhibitory concentration	Staphylococcus aureus	> 100.0 μg/mL	10.3390/md17070398 Marine Drugs
Antitumor	inhibitory activity	human cancer cells (MGC803; MDA-MB-231; C4-2B; A549)	Other compounds showed no inhibitory activities at concentrations of 5 μM in the preliminary screening.	10.3390/md17070398 Marine Drugs

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