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  3. [(E,2R,3R,4R,5R,8R)-2-[6-[(2S,3S)-3-acetyloxypentan-2-yl]-3,5-dimethyl-4-oxopyran-2-yl]-8-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)-4,6-dimethyl-5-propanoyloxynon-6-en-3-yl] 3-methylbutanoate

SCS-C003303

[(E,2R,3R,4R,5R,8R)-2-[6-[(2S,3S)-3-acetyloxypentan-2-yl]-3,5-dimethyl-4-oxopyran-2-yl]-8-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)-4,6-dimethyl-5-propanoyloxynon-6-en-3-yl] 3-methylbutanoate

Pathway: Polyketides Superclass: Linear polyketides Class: Open-chain polyketides
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Chemical Structure

Structure of [(E,2R,3R,4R,5R,8R)-2-[6-[(2S,3S)-3-acetyloxypentan-2-yl]-3,5-dimethyl-4-oxopyran-2-yl]-8-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)-4,6-dimethyl-5-propanoyloxynon-6-en-3-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.
Download: SDF SMILES

Source Information

Onchidium sp. (NA)
Original source name: Onchidium sp.|pulmonate mollusks
Kingdom Metazoa Phylum Mollusca Class Gastropoda Order Systellommatophora Family Onchidiidae Genus Onchidium Species NA
Hainan Island
DOI: 10.1021/np400483c  · Journal of Natural Products
pulmonate mollusks (NA)
Original source name: Onchidium sp.|pulmonate mollusks
Kingdom Metazoa Phylum Mollusca Class Gastropoda Order NA Family NA Genus NA Species NA
Hainan Island
DOI: 10.1021/np400483c  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
726.9 Da
Threshold ≤ 500
ALogP
8.60
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C42H62O10
Molecular Weight:
726.9480 Da
SMILES:
CCC(=O)O[C@@H](/C(C)=C/[C@@H](C)c1oc(CC)c(C)c(=O)c1C)[C@H](C)[C@@H](OC(=O)CC(C)C)[C@@H](C)c1oc([C@@H](C)[C@H](CC)OC(C)=O)c(C)c(=O)c1C
InChIKey:
YBYLWJQWQYRXKJ-JIBIURQTSA-N
InChI:
InChI=1S/C42H62O10/c1-16-32-24(8)36(46)26(10)38(49-32)22(6)20-23(7)39(50-34(44)18-3)29(13)42(51-35(45)19-21(4)5)30(14)41-28(12)37(47)27(11)40(52-41)25(9)33(17-2)48-31(15)43/h20-22,25,29-30,33,39,42H,16-19H2,1-15H3/b23-20+/t22-,25+,29+,30+,33+,39+,42-/m1/s1
Calculated Properties
ALogP:
8.604 lipophilicity
TPSA:
139.32 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
10
Rotatable Bonds:
17
Ring Count:
2 (2 aromatic)
Chiral Centers:
7
Fsp³:
0.6429 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003303
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Linear polyketides
NPClassifier Class:
Open-chain polyketides
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD24218

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged