SCS-C000074

11-hydroxy-4,7,15,18-tetramethyl-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-4,7,15,18-tetramethyl-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

389.4 Da

Threshold ≤ 500

ALogP

2.36

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C21H27NO6

Molecular Weight:

389.4480 Da

SMILES:

CC1COC2(C)Oc3c(c(O)c(C(N)=O)c4c3CC3C(C)COC3(C)O4)CC12

InChIKey:

                        HGKRRROATKYOHF-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C21H27NO6/c1-9-7-25-20(3)13(9)5-11-16(23)15(19(22)24)18-12(17(11)27-20)6-14-10(2)8-26-21(14,4)28-18/h9-10,13-14,23H,5-8H2,1-4H3,(H2,22,24)

Calculated Properties

ALogP:

2.358 lipophilicity

TPSA:

100.24 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.6667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000074

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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