Carotenoid DB: CA00422

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Carotenoids DB: CA00422

Entry

CA00422

Classification

C40 carotenoids including C40 originated apocarotenoids and intermediates
2.1 beta,beta Carotene
C40 Epoxycarotenoids

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

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Mol file

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Predict biological activities of this carotenoid
9'Z, 6,7--H, 5,6+H, 5',6'+H, 3-OH, 5-OH, 3'-OH, 5',6'-Epoxy, beta,beta
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Biological functions/Properties

Photosynthetic pigment of higher plants (Ref.503).

Antimicrobial activity - anti-H. pylori (Ref.492).

Number of
conjugated double bonds

Number of
conjugated multiple bonds

Isomers

InChI

InChIKey

Canonical SMILES

XLogP

10.319

Hydrogen Bond donors
(Lipinski's definition)

Hydrogen Bond Acceptors
(Lipinski's definition)

LipinskiFailures

Complexity of molecule

0.310

Number of heavy atoms

TPSA
(Topological Polar Surface Area)

73.220 Å²

Reaction

Substrate: CR00044, CR00046, CR00048, CR00091, CR00418

Product: CR00359, CR00383

Pathway

Pathway: CB000040, CB000080, CB000081

Major carotenoid information

Dominant pigment in chlorophytes, prasinophytes and in dinoflagellates (Ref.707).

Minor carotenoid information

Minor in euglenophytes, chlorarachniophytes and trebouxiophytes (Ref.707).

Source organisms

Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga (Chlorophyta - Chlamydomonadaceae)
Microdictyon boergesenii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Anadyomenaceae)
Basicladia sp. (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Chaetomorpha okamurae (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora horii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora kosterae (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Aegagrophila linnaei (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Chaetomorpha crassa (Ref.24, Ref.14) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora conchopheria (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora albida (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora coelothrix (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora japonica (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora pellucida (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora sericea (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora vagabunda (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Cladophora glomerata (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Rhizoclonium grande (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
Pithophora sp. (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
Wittrockiella lyallii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
Wittrockiella paradoxa (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
Cladophoropsis vaucheriaeformis (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
Cladophoropsis fasciculatus (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
Cladophoropsis membranacea (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
Siphonocladus tropicus (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
Tetraselmis chui (Ref.48, Ref.14) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
Pseudoscourfieldia marina (Ref.14) - Green alga: Prasinophyte (Chlorophyta - Pycnococcaceae)
Euglena gracilis (Ref.14) - Alga: Euglena (Euglenida - Euglenaceae)
Eutreptiella gymnastica (Ref.14) - Alga: Euglena (Euglenida - Eutreptiales)
Lepidodinium chlorophorum (Ref.673) - Alga: Green dinoflagellate, same as Gymnodinium chlorophorum ((Alveolata) - Gymnodiniaceae)
Pouteria sapota (Ref.773) - Land plant: red mamey sapote, species of tree native to Cuba and Central America. Fruit is commonly eaten in many Latin American countries. It is is about 10 to 25 cm (4 to 10 in) long and 8 to 12 cm (3 to 4.5 in) wide and has flesh ranging in color from pink to orange to red. The fruit's texture is creamy and soft, the flavor is a mix of sweet potato, pumpkin, honey, prune, peach, apricot, cantaloupe, cherry, and almond. (Streptophyta - Chrysophylloideae)
Malus domestica (Ref.492) - Land plant: Rosaceae: peel and flesh of apple fruits (Streptophyta - Rosaceae)

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.673: Antonio Gavalas-Olea, Susana Alvarez, Pilar Riobo, Francisco Rodriguez, Jose L. Garrido, and Belen Vaz, Org Lett. 2016 Sep 16;18(18):4642-5. Epub 2016 Sep 1., "19,19’-diacyloxy signature: an atypical level of structural evolution in carotenoid pigments", doi: 10.1021/acs.orglett.6b02272.

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.773: Attila Agócs et al., Journal of Food Composition and Analysis 65 (2018) 1–5, “Isolation of allene carotenoids from mamey”, http://dx.doi.org/10.1016/j.jfca.2017.04.004.

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”.

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

14660-91-4

Links to other DB

KEGG COMPOUND: C13431
LipidBank: VCA0059

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