Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA01012   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA01012                                                            

Classification
Carotenoid Name
Grasshopper ketone;
Icariside B1 aglycon;
(3S,5R,8R)-3,5-Dihydroxymegastigma-6,7-dien-9-one
IUPAC name (3S,5R,6R,8R)-9-Apo-6,7-didehydro-5,6-dihydro-3,5-dihydroxy-beta-carotene
Formula
C13H20O3
Molecular Weight 
224.29 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
2 including one ketone (2 in total)
Number of
conjugated multiple bonds 
2 including one ketone (2 in total)
Isomers 
  • Constitutional isomer: CA01021, CA01022, CA01207, CA01019, CA01014, CA01015, CA00805, CA00843
  • Conformer: CA01118
  • InChI
    InChI=1S/C13H20O3/c1-9(14)5-6-11-12(2,3)7-10(15)8-13(11,4)16/h5,10,15-16H,7-8H2,1-4H3/t6-,10-,13+/m0/s1
    InChIKey
    QMXLZUOHZGYGDY-ANSXDHORSA-N
    Canonical SMILES
    CC(=O)C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O
    XLogP
    2.331
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.167
    Number of heavy atoms
    16
    TPSA
    (Topological Polar Surface Area) 
    57.530 Å2
    Source organisms
    Solanum lyratum (Ref.394) - Land plant: Solanaceae: Inedible plant for humans
    Chenopodium album (Ref.530, Ref.167) - Land plant: white goosefoot, lamb's-quarters
    References
  • Ref.394 : Yue, Xi-dian; Yao, Fang; Zhang, Lei; Li, Gui-sheng; Dai, Sheng-jun, Zhongguo Zhongyao Zazhi (2014), 39(3), 453-456., "Sesquiterpenoids from Solanum lyratum".
  • Ref.530 : Huang FC1, Horváth G, Molnár P, Turcsi E, Deli J, Schrader J, Sandmann G, Schmidt H, Schwab W., Phytochemistry. 2009 Mar;70(4):457-64. doi: 10.1016/j.phytochem.2009.01.020. Epub 2009 Mar 4., "Substrate promiscuity of RdCCD1, a carotenoid cleavage oxygenase from Rosa damascena.".
  • Ref.167 : Della Greca, Marina; Di Marino, Cinzia; Zarrelli, Armando; D'Abrosca, Brigida, Journal of Natural Products, Volume67, Issue9, Pages1492-1495, Journal, 2004, CODEN:JNPRDF ISSN:0163-3864 DOI:10.1021/np049857q, "Isolation and phytotoxicity of apocarotenoids from Chenopodium album".
  • CAS
    41703-38-2
    Links to other DB
    KNApSAcK: C00031831

       Search other references with Google Scholar