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

SCS-C003243

[(E,2R,3R,4R,5R,8R)-8-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)-2-[6-[(2S,3S)-3-hydroxypentan-2-yl]-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)-8-(6-ethyl-3,5-dimethyl-4-oxopyran-2-yl)-2-[6-[(2S,3S)-3-hydroxypentan-2-yl]-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
684.9 Da
Threshold ≤ 500
ALogP
8.03
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C40H60O9
Molecular Weight:
684.9110 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](O)CC)c(C)c(=O)c1C
InChIKey:
ZDBVKIXZFFHSNZ-MANZRMSISA-N
InChI:
InChI=1S/C40H60O9/c1-15-30(41)23(8)38-26(11)35(45)27(12)39(49-38)29(14)40(48-33(43)18-20(4)5)28(13)37(47-32(42)17-3)22(7)19-21(6)36-25(10)34(44)24(9)31(16-2)46-36/h19-21,23,28-30,37,40-41H,15-18H2,1-14H3/b22-19+/t21-,23+,28+,29+,30+,37+,40-/m1/s1
Calculated Properties
ALogP:
8.033 lipophilicity
TPSA:
133.25 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
9
Rotatable Bonds:
16
Ring Count:
2 (2 aromatic)
Chiral Centers:
7
Fsp³:
0.6500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003243
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: CMNPD24217

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged