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(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol

PubChem CID
21630845
Structure
(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol_small.png
(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol_3D_Structure.png
Molecular Formula
Synonyms
  • Acuminoside
  • (2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol
  • 120163-17-9
  • CHEBI:183013
  • AKOS040736178
Molecular Weight
448.5 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2007-12-05
  • Modify:
    2025-01-18
Description
(2E)-3,7-Dimethyl-2,6-octadien-1-yl 6-O-[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydro-2-furanyl]-beta-D-glucopyranoside is a terpene glycoside.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]oxane-3,4,5-triol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C21H36O10/c1-12(2)5-4-6-13(3)7-8-28-19-17(25)16(24)15(23)14(31-19)9-29-20-18(26)21(27,10-22)11-30-20/h5,7,14-20,22-27H,4,6,8-11H2,1-3H3/b13-7+/t14-,15-,16+,17-,18+,19-,20-,21-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

RFFYIBOJHUSIGD-PHDUQKSESA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

CC(=CCC/C(=C/CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@](CO2)(CO)O)O)O)O)O)/C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H36O10
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 Nikkaji Number

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
448.5 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
448.23084734 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
448.23084734 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
158 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
619
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
8
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
471.2189
Instrument
Agilent 6530 Q-TOF
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
40 V
Retention Time
3.3537
Top 5 Peaks

335.0936 100

119.0822 49.28

107.0820 45.43

121.0949 39.91

105.0654 36.81

Thumbnail
Thumbnail
2 of 3
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MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
471.2189
Instrument
Agilent 6530 Q-TOF
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
20 V
Retention Time
3.3537
Top 5 Peaks

471.2164 100

335.0931 8.37

333.0768 4.66

201.1612 1.56

249.1375 1.50

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4.1.2 Other MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
471.2200654
Ionization Mode
positive
Retention Time
1.4166104359977851
Top 5 Peaks

335.0985234680541 0.07

401.1449718284997 0.07

333.0808550405062 0.06

367.1739771920188 0.06

91.05606340024603 0.06

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+NH4]+
Precursor m/z
466.2646704
Ionization Mode
positive
Retention Time
3.6008121142468927
Top 5 Peaks

259.17645378008376 0.09

273.1933855134789 0.07

258.17168578008375 0.07

272.18815851347887 0.05

243.1425573555427 0.04

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6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 Chemical Co-Occurrences in Literature

7.3 Chemical-Gene Co-Occurrences in Literature

7.4 Chemical-Disease Co-Occurrences in Literature

8 Biological Test Results

8.1 BioAssay Results

9 Taxonomy

10 Classification

10.1 ChEBI Ontology

10.2 MolGenie Organic Chemistry Ontology

11 Information Sources

CONTENTS