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Secoisolariciresinol 9,9'-diglucoside

PubChem CID
74328989
Structure
Secoisolariciresinol 9,9'-diglucoside_small.png
Molecular Formula
Synonyms
  • 148244-82-0
  • Secoisolariciresinol 9,9'-diglucoside
  • Seco-isolariciresinol diglucoside
  • rac Secoisolariciresinol Diglucoside
  • (+)-secoisolariciresinol diglucoside
Molecular Weight
686.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2014-06-12
  • Modify:
    2025-01-11
Description
Secoisolariciresinol 9,9'-diglucoside is a glycoside and a lignan.
Secoisolariciresinol 9,9'-diglucoside has been reported in Linum usitatissimum with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Secoisolariciresinol 9,9'-diglucoside.png

1.2 3D Status

Conformer generation is disallowed since too many undefined stereo centers

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SBVBJPHMDABKJV-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC1=C(C=CC(=C1)CC(COC2C(C(C(C(O2)CO)O)O)O)C(CC3=CC(=C(C=C3)O)OC)COC4C(C(C(C(O4)CO)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C32H46O16
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

158932-33-3

2.3.2 ChEBI ID

2.3.3 HMDB ID

2.3.4 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
686.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
16
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
15
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
686.27858538 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
686.27858538 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
258 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
48
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
861
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
12
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
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 2021.10.14)

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

685.26904 100

523.23212 1.70

535.91406 1.20

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2 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

327.15936 100

163.07727 99

137.05975 70.37

295.13504 39.34

189.09177 20.42

Thumbnail
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4.1.2 LC-MS

1 of 44
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Authors
Tetsuya Mori, Center for Sustainable Resource Science, RIKEN
Instrument
LC, Waters Acquity UPLC System; MS, Waters Xevo G2 Q-Tof
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
6V
Column Name
Acquity bridged ethyl hybrid C18 (1.7 um, 2.1 mm * 100 mm, Waters)
Retention Time
3.670633
Precursor m/z
687.2858619
Precursor Adduct
[M+H]+
Top 5 Peaks

327.15979 999

345.1694 668

363.18188 540

137.06097 528

163.07788 290

Thumbnail
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License
CC BY-NC-SA
Reference
Tsugawa H., Nakabayashi R., Mori T., Yamada Y., Takahashi M., Rai A., Sugiyama R., Yamamoto H., Nakaya T., Yamazaki M., Kooke R., Bac-Molenaar JA., Oztolan-Erol N., Keurentjes JJB., Arita M., Saito K. (2019) "A cheminformatics approach to characterize metabolomes in stable-isotope-labeled organisms" Nature Methods 16(4):295-298. [doi:10.1038/s41592-019-0358-2]
2 of 44
View All
Authors
Tetsuya Mori, Center for Sustainable Resource Science, RIKEN
Instrument
LC, Waters Acquity UPLC System; MS, Waters Xevo G2 Q-Tof
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
6V
Column Name
Acquity bridged ethyl hybrid C18 (1.7 um, 2.1 mm * 100 mm, Waters)
Retention Time
3.670633
Precursor m/z
687.2858619
Precursor Adduct
[M+H]+
Top 5 Peaks

363.17865 999

345.17419 549

686.28442 495

687.29944 365

687.27411 341

Thumbnail
Thumbnail
License
CC BY-NC-SA
Reference
Tsugawa H., Nakabayashi R., Mori T., Yamada Y., Takahashi M., Rai A., Sugiyama R., Yamamoto H., Nakaya T., Yamazaki M., Kooke R., Bac-Molenaar JA., Oztolan-Erol N., Keurentjes JJB., Arita M., Saito K. (2019) "A cheminformatics approach to characterize metabolomes in stable-isotope-labeled organisms" Nature Methods 16(4):295-298. [doi:10.1038/s41592-019-0358-2]

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Cytoplasm
  • Extracellular

9 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

10 Literature

10.1 Consolidated References

10.2 Chemical Co-Occurrences in Literature

10.3 Chemical-Gene Co-Occurrences in Literature

10.4 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

12 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

13 Classification

13.1 ChEBI Ontology

13.2 LOTUS Tree

13.3 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. ChEBI
  2. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    Secoisolariciresinol 9,9'-diglucoside
    https://www.wikidata.org/wiki/Q105249739
  3. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
    Secoisolariciresinol 9,9'-diglucoside
    https://foodb.ca/compounds/FDB015194
  4. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    Secoisolariciresinol 9,9'-diglucoside
    http://www.hmdb.ca/metabolites/HMDB0036323
  5. Natural Product Activity and Species Source (NPASS)
  6. MassBank Europe
  7. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  8. Wikidata
    Secoisolariciresinol 9,9'-diglucoside
    https://www.wikidata.org/wiki/Q105249739
  9. PubChem
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS