SCS-C003161

[(2S,3S,4S,5R,6R)-6-[(1R)-1-[3,5-dimethyl-4-oxo-6-[(2S,3S)-3-propanoyloxypentan-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] 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-[3,5-dimethyl-4-oxo-6-[(2S,3S)-3-propanoyloxypentan-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] 3-methylbutanoate

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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

700.9 Da

Threshold ≤ 500

ALogP

7.45

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:

C40H60O10

Molecular Weight:

700.9100 Da

SMILES:

CCC(=O)O[C@@H](CC)[C@H](C)c1oc([C@H](C)[C@@H]2O[C@](O)([C@@H](C)c3oc(CC)c(C)c(=O)c3C)[C@@H](C)[C@@H](OC(=O)CC(C)C)[C@@H]2C)c(C)c(=O)c1C

InChIKey:

                        MVXCAZJSLSAYPW-GKVXFRSOSA-N
                        
                    

InChI:

InChI=1S/C40H60O10/c1-15-29-20(6)33(43)24(10)38(47-29)27(13)40(45)28(14)39(48-32(42)18-19(4)5)26(12)37(50-40)25(11)36-23(9)34(44)22(8)35(49-36)21(7)30(16-2)46-31(41)17-3/h19,21,25-28,30,37,39,45H,15-18H2,1-14H3/t21-,25-,26+,27-,28-,30-,37-,39-,40+/m0/s1

Calculated Properties

ALogP:

7.449 lipophilicity

TPSA:

142.48 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.7000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C003161

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: CMNPD24213

Biological Activity Data

No bioactivity data available for this compound.

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