SCS-C003247

[(2S,3S,4S,5R,6R)-6-[(1R)-1-[3,5-dimethyl-4-oxo-6-[(2R)-3-oxopentan-2-yl]pyran-2-yl]ethyl]-2-[(1S)-1-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)ethyl]-2-hydroxy-3,5-dimethyloxan-4-yl] propanoate

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-[3,5-dimethyl-4-oxo-6-[(2R)-3-oxopentan-2-yl]pyran-2-yl]ethyl]-2-[(1S)-1-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)ethyl]-2-hydroxy-3,5-dimethyloxan-4-yl] propanoate

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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

614.8 Da

Threshold ≤ 500

ALogP

6.06

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:

C35H50O9

Molecular Weight:

614.7760 Da

SMILES:

CCC(=O)O[C@H]1[C@H](C)[C@H]([C@@H](C)c2oc([C@@H](C)C(=O)CC)c(C)c(=O)c2C)O[C@](O)([C@@H](C)c2oc(CC)c(C)c(=O)c2C)[C@H]1C

InChIKey:

                        UJZUDLBEBDDWIU-GPCQYSETSA-N
                        
                    

InChI:

InChI=1S/C35H50O9/c1-13-25(36)16(4)30-18(6)29(39)19(7)31(43-30)21(9)32-22(10)34(42-27(37)15-3)24(12)35(40,44-32)23(11)33-20(8)28(38)17(5)26(14-2)41-33/h16,21-24,32,34,40H,13-15H2,1-12H3/t16-,21-,22+,23-,24-,32-,34-,35+/m0/s1

Calculated Properties

ALogP:

6.060 lipophilicity

TPSA:

133.25 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.6571 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003247

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: CMNPD24210

Biological Activity Data

No bioactivity data available for this compound.

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