SCS-C003145

[(2S,3S,4S,5R,6R)-6-[(1R)-1-[6-[(2S,3S)-3-acetyloxypentan-2-yl]-3,5-dimethyl-4-oxopyran-2-yl]ethyl]-2-[(1S)-1-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)ethyl]-2-hydroxy-3,5-dimethyloxan-4-yl] 3-methylbutanoate

Pathway: Polyketides Superclass: Cyclic polyketides | Linear polyketides Class: 4-pyrone derivatives | Open-chain polyketides Glycoside

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Chemical Structure

Structure of [(2S,3S,4S,5R,6R)-6-[(1R)-1-[6-[(2S,3S)-3-acetyloxypentan-2-yl]-3,5-dimethyl-4-oxopyran-2-yl]ethyl]-2-[(1S)-1-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)ethyl]-2-hydroxy-3,5-dimethyloxan-4-yl] 3-methylbutanoate

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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.

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Source Information

Onchidium sp. (NA)

Kingdom Metazoa Phylum Mollusca Class Gastropoda Order Systellommatophora Family Onchidiidae Genus Onchidium Species NA

Hainan Island

DOI: 10.1021/np400483c · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

686.9 Da

Threshold ≤ 500

ALogP

7.06

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C39H58O10

Molecular Weight:

686.8830 Da

SMILES:

CCc1oc([C@H](C)[C@@]2(O)O[C@@H]([C@@H](C)c3oc([C@@H](C)[C@H](CC)OC(C)=O)c(C)c(=O)c3C)[C@@H](C)[C@H](OC(=O)CC(C)C)[C@@H]2C)c(C)c(=O)c1C

InChIKey:

                        NXWCTUPJJSSSHW-AIODOLTDSA-N
                        
                    

InChI:

InChI=1S/C39H58O10/c1-15-29-19(5)32(42)23(9)37(46-29)26(12)39(44)27(13)38(47-31(41)17-18(3)4)25(11)36(49-39)24(10)35-22(8)33(43)21(7)34(48-35)20(6)30(16-2)45-28(14)40/h18,20,24-27,30,36,38,44H,15-17H2,1-14H3/t20-,24-,25+,26-,27-,30-,36-,38-,39+/m0/s1

Calculated Properties

ALogP:

7.059 lipophilicity

TPSA:

142.48 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.6923 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003145

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Cyclic polyketides Linear polyketides

NPClassifier Class:

4-pyrone derivatives Open-chain polyketides

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD24212

Biological Activity Data

No bioactivity data available for this compound.

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