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20-Hydroxyecdysone 20,22-acetonide

PubChem CID
11060391
Structure
20-Hydroxyecdysone 20,22-acetonide_small.png
20-Hydroxyecdysone 20,22-acetonide_3D_Structure.png
Molecular Formula
Synonyms
  • Ecdysterone 20,22-monoacetonide
  • 22798-96-5
  • 20-Hydroxyecdysone 20,22-acetonide
  • Ecdysterone 20,22-moacetonide
  • CHEMBL2087536
Molecular Weight
520.7 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-10-26
  • Modify:
    2025-01-18
Description
Ecdysterone 20,22-monoacetonide has been reported in Stachyurus himalaicus, Sida spinosa, and Rhaponticum carthamoides with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
20-Hydroxyecdysone 20,22-acetonide.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C30H48O7/c1-25(2,34)11-10-24-29(7,37-26(3,4)36-24)23-9-13-30(35)18-14-20(31)19-15-21(32)22(33)16-27(19,5)17(18)8-12-28(23,30)6/h14,17,19,21-24,32-35H,8-13,15-16H2,1-7H3/t17-,19-,21+,22-,23-,24+,27+,28+,29+,30+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

GXNNYSDWRVKVJY-VUYJMULXSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@@]5([C@H](OC(O5)(C)C)CCC(C)(C)O)C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C30H48O7
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

22798-96-5

2.3.2 ChEMBL ID

2.3.3 DSSTox Substance ID

2.3.4 Nikkaji Number

2.3.5 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
520.7 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
520.34000387 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
520.34000387 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
116 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
37
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
988
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
10
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
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 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 LC-MS

1 of 8
View All
Authors
Nogawa T, Okano A, CSRS, RIKEN
Instrument
ABSciex API3200 LC/MS system
Instrument Type
LC-ESI-QQQ
MS Level
MS
Ionization Mode
POSITIVE
Precursor Adduct
[M+H]+
Top 5 Peaks

521 999

521.2 987

520.9 983

521.1 978

520.8 910

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License
CC BY
2 of 8
View All
Authors
Nogawa T, Okano A, CSRS, RIKEN
Instrument
Agilent 6410 Triple Quadrupole LC/MS system
Instrument Type
LC-ESI-QQQ
MS Level
MS2
Ionization Mode
POSITIVE
Precursor Adduct
[M+H]+
Top 5 Peaks

521.4 99

521.3 93

521.5 92

521.2 80

521.6 68

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License
CC BY

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

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

10 Classification

10.1 ChEMBL Target Tree

10.2 LOTUS Tree

10.3 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  2. EPA DSSTox
    20-Hydroxyecdysone 20,22-acetonide
    https://comptox.epa.gov/dashboard/DTXSID501346563
  3. Japan Chemical Substance Dictionary (Nikkaji)
  4. 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/
    Ecdysterone 20,22-monoacetonide
    https://www.wikidata.org/wiki/Q105023223
  5. MassBank Europe
  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. SpectraBase
    20-HYDROXYECDYSONE-20,22-MONOACETONIDE
    https://spectrabase.com/spectrum/2o6FB7Ng70u
    20-HYDROXYECDYSONE-20,22-MONOACETONIDE
    https://spectrabase.com/spectrum/KARAx0k4etC
  8. Wikidata
    (1S,3aS,5aR,7R,8S,9aR,9bR,11aR)-3a,7,8-trihydroxy-1-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-9a,11a-dimethyl-1H,2H,3H,5aH,6H,7H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-5-one
    https://www.wikidata.org/wiki/Q105023223
  9. PubChem
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS