Carotenoid DB: CA00701

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Carotenoids DB: CA00701

Entry

CA00701

Classification

C40 carotenoids including C40 originated apocarotenoids and intermediates
2.5 gamma,epsilon Carotene
C40 Ketones

Carotenoid Name

Prasinoxanthin

IUPAC name

(3S,6R,3'R,6'R)-3,6,3'-Trihydroxy-7,8-dihydro-gamma,epsilon-caroten-8-one

Formula

C40H56O4

Molecular Weight

600.848 g/mol

Structure

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Mol file

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(3S,6R,3'R,6'R), 7,8+H, 3-OH, 6-OH, 3'-OH, 8=O, gamma,epsilon
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Biological functions/Properties

Number of
conjugated double bonds

9 including one ketone (9 in total)

Number of
conjugated multiple bonds

9 including one ketone (9 in total)

Isomers

Constitutional isomer: CA00137, CA01092, CA01100, CA01101, CA00350, CA00347, CA00979, CA01093, CA01094, CA00348, CA00349, CA00346, CA00965, CA00415, CA00439, CA00440, CA00419, CA00441, CA00442, CA00443, CA00444, CA00445, CA00414, CA00421, CA00420, CA00417, CA00418, CA00416, CA00555, CA00584, CA00626, CA00631, CA00647, CA00648, CA00746, CA00745, CA00744, CA00747, CA00743, CA00785

InChI

InChIKey

Canonical SMILES

XLogP

8.661

Hydrogen Bond donors
(Lipinski's definition)

Hydrogen Bond Acceptors
(Lipinski's definition)

LipinskiFailures

Complexity of molecule

0.300

Number of heavy atoms

TPSA
(Topological Polar Surface Area)

77.760 Å²

Reaction

Substrate: CR00271

Product: CR00105, CR00168

Pathway

Pathway: CB000072, CB000073

Major carotenoid information

Dominant pigment in prasinophytes (Ref.707).

Minor carotenoid information

Occasionally found in dinoflagellates (Ref.707).

Source organisms

Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Bathycoccaceae)
Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
Micromonas pusilla (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Prasinococcales)
Pseudoscourfieldia marina (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Pycnococcaceae)
Pycnococcus provasolii (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Pycnococcaceae)
Arousa sp. (Ref.46) - Green alga: Prasinophyte (Unclassified chlorophyta - Unclassified chlorophyta)

References

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.707: Suzanne Roy et al., Phytoplankton Pigments Characterization, Chemotaxonomy and Applications in Oceanography, October 2011, Cambridge University Press, pp 665-674, "Part VII - Data sheets aiding identification of phytoplankton carotenoids and chlorophylls", available at http://www.cambridge.org/gb/files/2013/6697/5826/Data_sheets_part_3_Xanthophylls.pdf, ISBN: 9781107000667.

CAS

94705-97-2

Links to other DB

LipidBank: VCA1118

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