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Entry
CA00422                                                            

Classification
Carotenoid Name
(9'Z)-Neoxanthin;
9'-cis-Neoxanthin
IUPAC name (9'Z)-(3S,5R,6R,3'S,5'R,6'S)-5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-beta,beta-carotene-3,5,3'-triol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment of higher plants (Ref.503).
  • Antimicrobial activity - anti-H. pylori (Ref.492).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20-/t22-,33-,34-,38+,39+,40-/m0/s1
    InChIKey
    PGYAYSRVSAJXTE-OQASCVKESA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)/C)/C)/C=C/C=C(\C=C\[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C
    XLogP
    10.319
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.310
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    73.220 Å2
    Source organisms
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga
    Aegagrophila linnaei (Ref.24) - Green alga: Ulvophyceae
    Basicladia sp. (Ref.24) - Green alga: Ulvophyceae
    Chaetomorpha okamurae (Ref.24) - Green alga: Ulvophyceae
    Cladophora conchopheria (Ref.24) - Green alga: Ulvophyceae
    Cladophora horii (Ref.24) - Green alga: Ulvophyceae
    Cladophora kosterae (Ref.24) - Green alga: Ulvophyceae
    Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae
    Pithophora sp. (Ref.24) - Green alga: Ulvophyceae
    Wittrockiella lyallii (Ref.24) - Green alga: Ulvophyceae
    Wittrockiella paradoxa (Ref.24) - Green alga: Ulvophyceae
    Microdictyon boergesenii (Ref.24) - Green alga: Ulvophyceae
    Cladophoropsis fasciculatus (Ref.24) - Green alga: Ulvophyceae
    Cladophoropsis membranacea (Ref.24) - Green alga: Ulvophyceae
    Cladophoropsis vaucheriaeformis (Ref.24) - Green alga: Ulvophyceae
    Siphonocladus tropicus (Ref.24) - Green alga: Ulvophyceae
    Chaetomorpha crassa (Ref.24, Ref.14) - Green alga: Ulvophyceae
    Cladophora albida (Ref.24) - Green alga: Ulvophyceae
    Cladophora coelothrix (Ref.24) - Green alga: Ulvophyceae
    Cladophora glomerata (Ref.24) - Green alga: Ulvophyceae
    Cladophora japonica (Ref.24) - Green alga: Ulvophyceae
    Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae
    Cladophora pellucida (Ref.24) - Green alga: Ulvophyceae
    Cladophora sericea (Ref.24) - Green alga: Ulvophyceae
    Cladophora vagabunda (Ref.24) - Green alga: Ulvophyceae
    Rhizoclonium grande (Ref.24) - Green alga: Ulvophyceae
    Euglena gracilis (Ref.14) - Alga: Euglenoid
    Eutreptiella gymnastica (Ref.14) - Alga: Euglenoid
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
    Pseudoscourfieldia marina (Ref.14) - Green alga: Prasinophyte
    Tetraselmis chui (Ref.48, Ref.14) - Green alga: Chlorodendraceae
    Malus domestica (Ref.492) - Land plant: Rosaceae: apple peel extract
    References
  • Ref.12 : N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".
  • Ref.13 : PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".
  • Ref.14 : S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".
  • Ref.24 : Y. Yoshii, I,. Wakana, K. Miriya, S. Arai, K. Ueda, and I. Inouye, J. Phycol. 40, 1170-1177 (2004) "Carotenoid comositions of Cladophora Balls (Aegagropila linnaei) and some members of the Cladophorales (Ulvophyceae, Chlorophyta): their taxonomic and evolutionary implication".
  • Ref.46 : E. S. Egeland, R. R. L. Guillard, and S. Liaaen-Jensen, Phytochemistry, Vol. 44, No. 6, pp.1087-1097, 1997, "Additional carotenoid prototype representatices and general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta)".
  • Ref.47 : E. S. Egeland, W. Eikrem, J. Throndsen, C. Wilhelm, M. Zapata, and S. Liaaen-Jensen, Biochemical systematics and Ecology, Vol. 23, NO. 7/8, pp. 747-755, 1995 "Carotenoids from Further Prasinophytes".
  • Ref.48 : Jose L. Carrido, Francisco Rodriguez, and Mannuel Zapata J. Phycol. 15, 366-374 (2009) "Occurrence of Loroxanthin, Loroxanthin decenoate, and Loroxanthin dodecenoate in Tetraselmis species (Prasinophyceae, Chlorophyta)".
  • Ref.492 : Péter Molnár, József Deli, Toru Tanaka,Yoshiyuki Kann, Satoru Tani, Nóra Gyémánt, Joseph Molnár ,and Masami Kawase, Phytotherapy Research, Volume 24, Issue 5, pages 644–648, May 2010, “Carotenoids with anti-Helicobacter pylori activity from Golden deliciousapple”.
  • Ref.503 : Javier de las Rivas, Anunciacion Abadia, and Javier Abadia, Plant Physiol. (1989) 91, 190-192, “A New Reversed Phase-HPLC Method Resolving All Major Higher Plant Photosynthetic Pigments1”.
  • CAS
    14660-91-4
    Links to other DB
    KEGG COMPOUND: C13431
    LipidBank: VCA0059

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