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Icarin

PubChem CID
5471129
Structure
Icarin_small.png
Molecular Formula
Synonyms
  • Icarin
  • Icariine
  • 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one
  • Icarrin
  • SCHEMBL7738609
Molecular Weight
676.7 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
Icarin is a glycoside and a member of flavonoids.
5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one has been reported in Epimedium brevicornu, Epimedium pubescens, and other organisms with data available.
See also: Icariin (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Icarin.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

5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

TZJALUIVHRYQQB-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C33H40O15
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 HMDB ID

2.3.3 NSC Number

2.3.4 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-(4'-methoxyphenyl)-3-rhamnosido-5-hydroxyl-7-glucosido-8-(3'-methyl-2-butylenyl)-4-chromanone
  • icarrin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
676.7 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
1.7
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
8
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
15
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
676.23672056 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
676.23672056 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
234 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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
1170
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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
10
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 2019.01.04)

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

531.1825 100

369.1307 32.85

677.2399 28.10

313.0667 3.17

129.0534 1.97

Thumbnail
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2 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

369.1321 100

531.1856 58.81

313.0695 4.94

129.0535 2.97

301.0704 1.01

Thumbnail
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4.1.2 LC-MS

1 of 9
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
677.2386
Instrument
LCMS-IT-TOF
Instrument Type
LC-ESI-ITTOF
Ionization Mode
positive
Retention Time
15.305300 min
Top 5 Peaks

369.138400 100

313.066800 79.23

370.136100 20.70

531.174400 16.40

532.193700 5.37

Thumbnail
Thumbnail
License
CC BY-SA
2 of 9
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
LCMS-IT-TOF
Instrument Type
LC-ESI-ITTOF
Ionization Mode
negative
Retention Time
14.846667 min
Top 5 Peaks

735.260200 100

513.181000 64.32

789.216100 49.88

736.250700 41.96

514.182800 20.62

Thumbnail
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License
CC BY-SA

4.1.3 Other MS

1 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
677.243997
Ionization Mode
positive
Retention Time
3.556004367
Top 5 Peaks

369.133897 0.83

71.048383 0.04

85.027735 0.04

313.073757 0.03

536.962096 0.02

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
677.243997
Ionization Mode
positive
Retention Time
3.5287222118626382
Top 5 Peaks

313.09886387783956 0.79

243.08189344416456 0.07

353.1360814104495 0.02

215.0836176415512 0.02

312.0867698778396 0.02

Thumbnail
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6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

8.5 Chemical-Gene Co-Occurrences in Patents

9 Biological Test Results

9.1 BioAssay Results

10 Taxonomy

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

11 Classification

11.1 MeSH Tree

11.2 ChEBI Ontology

11.3 LOTUS Tree

11.4 MolGenie Organic Chemistry Ontology

12 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/
    5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one
    https://www.wikidata.org/wiki/Q105268203
  3. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  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
    5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one
    http://www.hmdb.ca/metabolites/HMDB0246694
  5. Natural Product Activity and Species Source (NPASS)
  6. 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
  7. Wikidata
    5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one
    https://www.wikidata.org/wiki/Q105268203
  8. PubChem
  9. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  11. PATENTSCOPE (WIPO)
CONTENTS