Violaxanthin

Details

• Internal ID: 584b6dcb-688c-4824-a432-c88c7eb5063b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Tetraterpenoids > Carotenoids > Xanthophylls
• IUPAC Name: (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
• InChI: InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1
• InChI Key: SZCBXWMUOPQSOX-WVJDLNGLSA-N
• Popularity: 417 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 600.90 g/mol
• Exact Mass: 600.41786026 g/mol
• Topological Polar Surface Area (TPSA): 65.50 Ų
• XlogP: 9.80
• Atomic LogP (AlogP): 8.97
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• 126-29-4
• all-trans-Violaxanthin
• trans-Violaxanthin
• Zeaxanthin diepoxide
• CHEBI:35288
• E 161e
• (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
• 51C926029A
• DTXSID901016934
• 5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta-carotene-3,3'-diol
• (3S,3'S,5R,5'R, 6S,6'S)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
• (1R,3S,6S)-6-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)heptan-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl)-1,5,5-trimethyl-7-oxabicyclo(4.1.0)heptan-3-ol
• RefChem:194378
• CHEBI:27295
• DTXCID001475117
• beta,beta-Carotene-3,3'-diol, 5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-
• Violoxanthin
• (3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'- TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
• (3S,3'S,5R,5'R,6S,6'S)-5,5',6,6'-tetrahydro-5,6:5',6'-diepoxy-beta,beta-carotene-3,3'-diol
• XAT
• UNII-51C926029A
• all-trans-Violaxanthin;Zeaxanthin diepoxide;5a,6a:5'a,6'a-Bisoxy-5,5',6,6'-tetrahydro-b,b-carotene-3b,3b'-diol
• ALL-E-VIOLAXANTHIN
• VIOLAXANTHIN [MI]
• C ORANGE 15
• SCHEMBL97720
• ANTI,ANTI-VIOLAXANTHIN
• orb1680038
• VIOLAXANTHIN, ALL-TRANS-
• VIOLAXANTHIN (E 161E)
• Violaxanthin - solution in ethanol
• (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
• HY-N9625
• Violaxanthin, >=90.0% (HPLC)
• LMPR01070282
• MSK159340
• AKOS040763713
• DB03460
• FV46272
• FV61389
• CS-0202315
• NS00070421
• C08614
• Q607883
• 09958A8F-4AFE-43DB-9034-C562F62D8ABD
• 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene-3,3'-diol
• .BETA.-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-
• 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-.BETA.-CAROTENE-3,3'-DIOL
• (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
• (3S,3'S,5R,5'R, 6S,6'S)-5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-.BETA.,.BETA.-CAROTENE-3,3'-DIOL
• (3S,3'S,5R,5'R,6S,6'S)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
• (3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
• .BETA.,.BETA.-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-, (3S,3'S,5R,5'R,6S,6'S)-
• b,b-Carotene-3,3'-diol,5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	-	0.8134	81.34%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4735	47.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8782	87.82%
OATP1B3 inhibitior	+	0.9625	96.25%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9912	99.12%
P-glycoprotein inhibitior	+	0.7620	76.20%
P-glycoprotein substrate	-	0.8311	83.11%
CYP3A4 substrate	+	0.6047	60.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7596	75.96%
CYP3A4 inhibition	-	0.8778	87.78%
CYP2C9 inhibition	-	0.8314	83.14%
CYP2C19 inhibition	-	0.7199	71.99%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.8519	85.19%
CYP2C8 inhibition	-	0.8661	86.61%
CYP inhibitory promiscuity	-	0.8434	84.34%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8720	87.20%
Carcinogenicity (trinary)	Non-required	0.5157	51.57%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.8904	89.04%
Skin irritation	-	0.6620	66.20%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8134	81.34%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.7046	70.46%
skin sensitisation	-	0.5767	57.67%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6237	62.37%
Acute Oral Toxicity (c)	III	0.3944	39.44%
Estrogen receptor binding	+	0.8511	85.11%
Androgen receptor binding	+	0.7349	73.49%
Thyroid receptor binding	+	0.6812	68.12%
Glucocorticoid receptor binding	+	0.7672	76.72%
Aromatase binding	+	0.5929	59.29%
PPAR gamma	+	0.7297	72.97%
Honey bee toxicity	-	0.7802	78.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9004	90.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.07%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	91.79%	83.82%
CHEMBL2061	P19793	Retinoid X receptor alpha	85.65%	91.67%
CHEMBL1870	P28702	Retinoid X receptor beta	84.44%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.35%	89.00%
CHEMBL2004	P48443	Retinoid X receptor gamma	83.51%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.30%	92.94%
CHEMBL259	P32245	Melanocortin receptor 4	82.78%	95.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.80%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.15%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	80.09%	90.17%

Plants that contains it

• Acacia adunca
• Aconitum burnatii
• Adiantum philippense
• Agastache foeniculum
• Agnorhiza bolanderi
• Allium rotundum
• Aloe arborescens
• Alseodaphne paludosa
• Anaxagorea crassipetala
• Annona cornifolia
• Annona impressivenia
• Arabidopsis thaliana
• Araujia sericifera
• Arnica nevadensis
• Artemisia campestris subsp. variabilis
• Artemisia gmelinii
• Asparagus falcatus
• Astragalus sempervirens
• Bersama yangambiensis
• Beyeria sulcata var. brevipes
• Brassica oleracea
• Bursaria spinosa
• Calamus draco
• Caloncoba echinata
• Calostephane divaricata
• Camellia sasanqua
• Capsicum annuum
• Caragana aurantiaca
• Carica papaya
• Castanopsis sclerophylla
• Celastrus orbiculatus
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Citrus trifoliata
• Coffea arabica
• Cordylanthus kingii
• Craibia grandiflora
• Crepis tectorum
• Croton cascarilloides
• Croton megistocarpus
• Cucurbita maxima
• Diospyros kaki
• Dipterocarpus alatus
• Disynaphia halimifolia
• Drosera peltata
• Dumortiera hirsuta
• Echeveria secunda
• Echinops amplexicaulis
• Equisetum fluviatile
• Eragrostis viscosa
• Eschscholzia californica
• Eucalyptus melliodora
• Euonymus japonicus
• Excoecaria acerifolia
• Ficus formosana
• Forsteronia refracta
• Fridericia chica
• Gardenia fosbergii
• Garrya laurifolia
• Geranium sibiricum
• Ginkgo biloba
• Gnetum latifolium
• Goniothalamus malayanus
• Goupia glabra
• Grewia mollis
• Griffitharia pallescens
• Gymnocarpium robertianum
• Hedysarum inundatum
• Heliotropium floridum
• Hemerocallis fulva var. angustifolia
• Heterotheca grandiflora
• Hovenia acerba
• Hypericum laricifolium
• Ilex affinis
• Impatiens noli-tangere
• Ipomoea digitata
• Iris pseudacorus
• Isodon umbrosus
• Juglans nigra
• Kaempferia marginata
• Kaempferia pulchra
• Kaunia saltensis
• Lagerstroemia indica
• Laggera alata
• Lepisorus ussuriensis
• Litogyne gariepina
• Lysimachia mauritiana
• Machilus japonica
• Mangifera indica
• Marrubium anisodon
• Medinilla magnifica
• Mesua ferrea
• Metasequoia glyptostroboides
• Momordica charantia
• Moringa oleifera
• Nauclea officinalis
• Naucleopsis ternstroemiiflora
• Neltuma glandulosa
• Ocotea pittieri
• Odixia angusta
• Onobrychis bobrovii
• Orobanche owerinii
• Panzerina lanata
• Papaver persicum
• Passiflora edulis
• Pastinaca sativa
• Peltostigma guatemalense
• Perilla frutescens
• Petteria ramentacea
• Pittosporum tobira
• Premna odorata
• Prunus laurocerasus
• Prunus persica
• Pseudocydonia sinensis
• Pteris quadriaurita
• Pyrus communis
• Quercus cerris
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Ruta pinnata
• Salvia dorrii
• Salvia officinalis
• Salvia syriaca
• Sandea japonica
• Scutellaria amoena
• Senecio cathcartensis
• Senecio isatideus
• Senecio johnstonii var. kilimanjari
• Senecio squalidus
• Sequoia sempervirens
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Solanum laxum
• Solanum tuberosum
• Sophora flavescens var. flavescens
• Spinacia oleracea
• Stenostomum lucidum
• Stevia polycephala
• Strobilanthes cusia
• Swertia franchetiana
• Syncarpha gnaphaloides
• Taxodium mucronatum
• Terminalia catappa
• Teucrium cubense
• Thymus piperella
• Trichilia rubescens
• Trigonella foenum-graecum
• Uraria picta
• Vaccinium oxycoccos
• Viguiera incana
• Viola tricolor
• Viscum album
• Vitex madiensis
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum
• Zea mays
• Zostera marina

Cross-Links

• PubChem: 448438
• NPASS: NPC10559
• LOTUS: LTS0102265
• wikiData: Q607883