SCS-C000073

11-hydroxy-N,4,7,15,18-pentamethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.02,10.04,8.015,19]icosa-1,10,12-triene-12-carboxamide

Pathway: Polyketides Superclass: Cyclic polyketides Class: Fungal cyclic polyketides (Miscellaneous)

Chemical Structure

Structure of 11-hydroxy-N,4,7,15,18-pentamethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.02,10.04,8.015,19]icosa-1,10,12-triene-12-carboxamide

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Source Information

N/A

South China Sea

DOI: 10.3390/md8041094 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

403.5 Da

Threshold ≤ 500

ALogP

2.62

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H29NO6

Molecular Weight:

403.4750 Da

SMILES:

CNC(=O)c1c(O)c2c(c3c1OC1(C)OCC(C)C1C3)OC1(C)OCC(C)C1C2

InChIKey:

                        OEJKOJFJDJCAAF-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C22H29NO6/c1-10-8-26-21(3)14(10)6-12-17(24)16(20(25)23-5)19-13(18(12)28-21)7-15-11(2)9-27-22(15,4)29-19/h10-11,14-15,24H,6-9H2,1-5H3,(H,23,25)

Calculated Properties

ALogP:

2.619 lipophilicity

TPSA:

86.25 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.6818 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000073

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Cyclic polyketides

NPClassifier Class:

Fungal cyclic polyketides (Miscellaneous)

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
Antitumor	IC50	KB, KBv200, MCF-7, MCF-7/adr, A549	> 50.0 μM	10.3390/md8041094 Marine Drugs

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