An official website of the United States government

Dehydrodihydrorotenone

PubChem CID
3950722
Structure
Dehydrodihydrorotenone_small.png
Dehydrodihydrorotenone_3D_Structure.png
Molecular Formula
Synonyms
  • Dehydrodihydrorotenone
  • 16,17-dimethoxy-6-propan-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one
  • KBio2_005802
  • 16,17-dimethoxy-6-propan-2-yl-2,7,20-trioxapentacyclo(11.8.0.03,11.04,8.014,19)henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one
  • Spectrum_000186
Molecular Weight
394.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-09-12
  • Modify:
    2025-01-11
Description
LSM-4404 is a member of rotenones.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dehydrodihydrorotenone.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

16,17-dimethoxy-6-propan-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,11,16H,8,10H2,1-4H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC(C)C1CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C23H22O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 ChEMBL ID

2.3.3 Lipid Maps ID (LM_ID)

2.3.4 Metabolomics Workbench ID

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
394.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
394.14163842 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
394.14163842 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
687
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
1
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)

3.2 Experimental Properties

3.2.1 Collision Cross Section

177.94 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

185.29 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
194.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.3 Chemical Classes

3.3.1 Lipids

Polyketides [PK] -> Flavonoids [PK12] -> Rotenoid flavonoids [PK1206]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Instrument Name
Jeol PS-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
395.1478
Instrument
Agilent 6530 Q-TOF
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
40 V
Retention Time
5.975
Top 5 Peaks

279.0619 100

335.1288 76.20

293.0505 68.93

264.0438 61.28

280.0689 49.10

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
395.1478
Instrument
Agilent 6530 Q-TOF
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Collision Energy
20 V
Retention Time
5.975
Top 5 Peaks

395.1425 100

364.1272 34.39

335.1271 30.55

363.1268 24.73

349.1043 8.68

Thumbnail
Thumbnail

4.2.2 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
395.1489149
Ionization Mode
positive
Retention Time
5.917435442
Top 5 Peaks

363.124533 0.30

364.132466 0.25

335.129589 0.22

307.061484 0.06

339.08771 0.04

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
395.1489149
Ionization Mode
positive
Retention Time
5.975075170054322
Top 5 Peaks

152.07097365532383 0.14

264.06548594517227 0.08

236.06422473917232 0.05

150.05612865532382 0.05

279.0912154101723 0.05

Thumbnail
Thumbnail

6 Chemical Vendors

7 Literature

7.1 Consolidated References

8 Patents

8.1 Depositor-Supplied Patent Identifiers

9 Biological Test Results

9.1 BioAssay Results

10 Classification

10.1 ChEBI Ontology

10.2 LIPID MAPS Classification

10.3 ChEMBL Target Tree

10.4 CCSBase Classification

10.5 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  2. ChEBI
  3. 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
  4. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  5. 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
  6. Metabolomics Workbench
  7. SpectraBase
    21,22-Dihydro-6,12a-didehydro-rotenone
    https://spectrabase.com/spectrum/LcAMn3vNimo
  8. Wikidata
  9. PubChem
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS