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  3. (2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-6-butoxy-4-hydroxy-2-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl]oxy-6-methyloxane-3,4,5-triol

SCS-C004151

(2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-6-butoxy-4-hydroxy-2-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Pathway: Carbohydrates Superclass: Saccharides Class: Polysaccharides Glycoside
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Chemical Structure

Structure of (2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-6-butoxy-4-hydroxy-2-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl]oxy-6-methyloxane-3,4,5-triol
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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

Asterias amurensis (NA)
Kingdom Metazoa Phylum Echinodermata Class Asteroidea Order Forcipulatida Family Asteriidae Genus Asterias Species Asterias amurensis
Beihai
DOI: 10.1080/14786410903034330  · Natural Product Research

Drug-likeness (Lipinski Ro5)

Molecular Weight
658.7 Da
Threshold ≤ 500
ALogP
-3.81
Threshold ≤ 5
H-Bond Donors
9
Threshold ≤ 5
H-Bond Acceptors
17
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C28H50O17
Molecular Weight:
658.6910 Da
SMILES:
CCCCO[C@@H]1O[C@H](C)[C@@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](C)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](C)[C@@H](O)[C@H](O)[C@H]1O
InChIKey:
MIMANUGFNRXKBB-FYTLCGAYSA-N
InChI:
InChI=1S/C28H50O17/c1-6-7-8-38-27-24(45-26-20(36)17(33)14(30)10(3)40-26)21(37)22(12(5)42-27)43-28-23(18(34)15(31)11(4)41-28)44-25-19(35)16(32)13(29)9(2)39-25/h9-37H,6-8H2,1-5H3/t9-,10-,11-,12-,13+,14-,15+,16+,17+,18+,19-,20-,21+,22-,23-,24-,25+,26-,27-,28+/m1/s1
Calculated Properties
ALogP:
-3.814 lipophilicity
TPSA:
255.91 Ų polar surface area
H-Bond Donors:
9
H-Bond Acceptors:
17
Rotatable Bonds:
10
Ring Count:
4 (0 aromatic)
Chiral Centers:
20
Fsp³:
1.0000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C004151
NPClassifier Pathway:
Carbohydrates
NPClassifier Superclass:
Saccharides
NPClassifier Class:
Polysaccharides
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD20555

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged