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Entry
CA00269                                                            

Classification
Carotenoid Name
K-G;
1'-Hydroxy-4-keto-γ-carotene glucoside;
1'-OH-4-Keto-γ-carotene glucoside;
1'-Hydroxy-4-keto-gamma-carotene glucoside;
1'-OH-4-Keto-gamma-carotene glucoside
IUPAC name 1'-(beta-D-Glucopyranosyloxy)-1',2'-dihydro-beta,psi-caroten-4-one
Formula
C46H66O7
Molecular Weight 
730.988 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
12 includingone ketone (12 in total)
Number of
conjugated multiple bonds 
12 includingone ketone (12 in total)
Isomers 
  • Constitutional isomer: CA00103, CA00946, CA00230, CA00961, CA00212, CA00240, CA00211, CA00561
  • InChI
    InChI=1S/C46H66O7/c1-32(17-11-12-18-33(2)20-15-24-36(5)26-27-38-37(6)39(48)28-30-45(38,7)8)19-13-21-34(3)22-14-23-35(4)25-16-29-46(9,10)53-44-43(51)42(50)41(49)40(31-47)52-44/h11-15,17-24,26-27,40-44,47,49-51H,16,25,28-31H2,1-10H3/b12-11+,19-13+,20-15+,22-14+,27-26+,32-17+,33-18+,34-21+,35-23+,36-24+/t40-,41-,42+,43-,44+/m1/s1
    InChIKey
    PLZRVZWMWJQZSE-VPWKDHIOSA-N
    Canonical SMILES
    OC[C@H]1O[C@@H](OC(CCC/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C)C(=O)CCC2(C)C)\C)\C)/C)/C)/C)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
    XLogP
    10.471
    Hydrogen Bond donors
    (Lipinski's definition)
    4
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    7
    LipinskiFailures
    2
    Complexity of molecule
    0.311
    Number of heavy atoms
    53
    TPSA
    (Topological Polar Surface Area) 
    116.450 Å2
    Source organisms
    Rhodococcus rhodochrous RNMS1 (Ref.217) - Actinobacteria
    References
  • Ref.217 : Takaichi, Shinichi; Ishidsu, Junichi; Seki, Toshinori; Fukada, Shigeo, Agricultural and Biological Chemistry (1990), 54(8), 1931-7., "Carotenoid pigments from Rhodococcus rhodochrous RNMS1:  two monocyclic carotenoids, a carotenoid monoglycoside and carotenoid glycoside monoesters".
  • CAS
    130137-24-5
    Links to other DB
    KNApSAcK: C00022994
    LipidBank: VCA1091

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