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Usararotenoid C

PubChem CID
641748
Structure
Usararotenoid C_small.png
Usararotenoid C_3D_Structure.png
Molecular Formula
Synonyms
  • Usararotenoid C
  • (6aR,12aS)-2,3-Methylenedioxy-9-methoxy-8-(3,3-dimethylallyl)-12a-hydroxyrotenoid
  • (6aR,12aS)-12a-hydroxy-9-methoxy-8-(3-methylbut-2-en-1-yl)-6a,12a-dihydrochromeno[2,3-c][1,3]dioxolo[4,5-g]chromen-12(6H)-one
  • 1,3-dioxolo[6,7][1]benzopyrano[3,4-b][1]benzopyran-12(6H)-one, 6a,12a-dihydro-12a-hydroxy-9-methoxy-8-(3-methyl-2-butenyl)-, (6aR,12aS)-
  • (1S,13R)-1-hydroxy-17-methoxy-16-(3-methylbut-2-enyl)-5,7,11,14-tetraoxapentacyclo(11.8.0.02,10.04,8.015,20)henicosa-2,4(8),9,15(20),16,18-hexaen-21-one
Molecular Weight
410.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2006-01-25
  • Modify:
    2025-01-18
Description
Usararotenoid C has been reported in Millettia usaramensis with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Usararotenoid C.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,13R)-1-hydroxy-17-methoxy-16-(3-methylbut-2-enyl)-5,7,11,14-tetraoxapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-one
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C23H22O7/c1-12(2)4-5-13-16(26-3)7-6-14-21(13)30-20-10-27-17-9-19-18(28-11-29-19)8-15(17)23(20,25)22(14)24/h4,6-9,20,25H,5,10-11H2,1-3H3/t20-,23+/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

ZFSLOJRJABHMTL-OFNKIYASSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC(=CCC1=C(C=CC2=C1O[C@@H]3COC4=CC5=C(C=C4[C@]3(C2=O)O)OCO5)OC)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C23H22O7
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 ChEMBL ID

2.3.2 Metabolomics Workbench ID

2.3.3 Nikkaji Number

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
410.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
3.8
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
410.13655304 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
410.13655304 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
83.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
704
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
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

1D NMR Spectra

4.1.1 13C NMR Spectra

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 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H2O+H]+
Precursor m/z
393.133
Instrument
Maxis II HD Q-TOF Bruker
Ionization Mode
positive
Top 5 Peaks

309.075806 100

393.133209 73.40

335.127594 49.79

363.123016 43.27

365.138214 38.25

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2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+K]+
Precursor m/z
449.1
Instrument
Maxis II HD Q-TOF Bruker
Ionization Mode
positive
Top 5 Peaks

287.054565 100

303.052185 35.83

288.057404 8.99

287.016754 5.65

85.029091 5.41

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6 Literature

6.1 Consolidated References

6.2 Chemical Co-Occurrences in Literature

6.3 Chemical-Gene Co-Occurrences in Literature

6.4 Chemical-Disease Co-Occurrences in Literature

7 Biological Test Results

7.1 BioAssay Results

8 Taxonomy

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

9 Classification

9.1 LOTUS Tree

9.2 MolGenie Organic Chemistry Ontology

10 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. Japan Chemical Substance Dictionary (Nikkaji)
  3. 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/
  4. Natural Product Activity and Species Source (NPASS)
  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. NMRShiftDB
  8. SpectraBase
    USARAROTENOID-C;(6AR,12AS)-2,3-METHYLENE-DIOXY-9-METHOXY-8-(3,3-DIMETHYLALLYL)-12A-HYDROXYROTENOID
    https://spectrabase.com/spectrum/7ouYyXw5m8G
  9. Wikidata
  10. PubChem
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS