Adonixanthin

Details

• Internal ID: 9f644d93-7f52-4c48-8b7b-729d62ec7484
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Tetraterpenoids > Carotenoids > Xanthophylls
• IUPAC Name: (6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)C(CC2(C)C)O)C)C)C
• SMILES (Isomeric): CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2=C(C(=O)[C@H](CC2(C)C)O)C)/C)/C
• InChI: InChI=1S/C40H54O3/c1-28(17-13-19-30(3)21-23-35-32(5)25-34(41)26-39(35,7)8)15-11-12-16-29(2)18-14-20-31(4)22-24-36-33(6)38(43)37(42)27-40(36,9)10/h11-24,34,37,41-42H,25-27H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,28-15+,29-16+,30-19+,31-20+/t34-,37+/m1/s1
• InChI Key: YECXHLPYMXGEBI-ZNQVSPAOSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₄O₃
• Molecular Weight: 582.90 g/mol
• Exact Mass: 582.40729558 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 10.60
• Atomic LogP (AlogP): 9.73
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• Doradexanthin
• 4-Ketozeaxanthin
• 4-Keto-zeaxanthin
• (3S,3'R)-Adonixanthin
• 3,3'-Dihydroxyechinenone
• beta-Doradexanthin
• All-trans-beta-doradexanthin
• PSZ3Q7662U
• (3S,3'R)-4-Keto-zeaxanthin
• UNII-PSZ3Q7662U
• Adonixanthin/ 4-Ketozeaxanthin
• beta-Caroten-4-one, 3,3'-dihydroxy-
• beta,beta-Caroten-4-one, 3,3'-dihydroxy-, (3S,3'R)-
• (3S,3'R)-3,3'-Dihydroxy-beta,beta-caroten-4-one
• 4418-73-9
• all-trans-adonixanthin
• .BETA.-DORADEXANTHIN
• SCHEMBL14519499
• CHEBI:80217
• LMPR01070016
• ALL-TRANS-.BETA.-DORADEXANTHIN
• 3,3'-dihydroxy-4-keto-beta,beta-carotene
• 3,3'-Dihydroxy-beta,beta-carotene-4-one
• (3S,3'R)-dihydroxy-4-keto-beta,beta-carotene
• .BETA.-CAROTEN-4-ONE, 3,3'-DIHYDROXY-
• Q27149334
• (3S,3'R)-3,3'-DIHYDROXY-.BETA.,.BETA.-CAROTEN-4-ONE
• .BETA.,.BETA.-CAROTEN-4-ONE, 3,3'-DIHYDROXY-, (3S,3'R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	-	0.7967	79.67%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8154	81.54%
OATP2B1 inhibitior	-	0.7121	71.21%
OATP1B1 inhibitior	+	0.8108	81.08%
OATP1B3 inhibitior	+	0.9646	96.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8100	81.00%
P-glycoprotein substrate	-	0.6955	69.55%
CYP3A4 substrate	+	0.6434	64.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.8897	88.97%
CYP2C9 inhibition	-	0.8204	82.04%
CYP2C19 inhibition	-	0.7036	70.36%
CYP2D6 inhibition	-	0.9406	94.06%
CYP1A2 inhibition	-	0.9298	92.98%
CYP2C8 inhibition	-	0.7825	78.25%
CYP inhibitory promiscuity	-	0.8099	80.99%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7928	79.28%
Carcinogenicity (trinary)	Non-required	0.5582	55.82%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9078	90.78%
Skin irritation	-	0.6629	66.29%
Skin corrosion	-	0.9618	96.18%
Ames mutagenesis	-	0.5591	55.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.8143	81.43%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7809	78.09%
skin sensitisation	+	0.7925	79.25%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.8538	85.38%
Acute Oral Toxicity (c)	III	0.7264	72.64%
Estrogen receptor binding	+	0.8330	83.30%
Androgen receptor binding	+	0.8317	83.17%
Thyroid receptor binding	+	0.7164	71.64%
Glucocorticoid receptor binding	+	0.8876	88.76%
Aromatase binding	-	0.5304	53.04%
PPAR gamma	+	0.7363	73.63%
Honey bee toxicity	-	0.8249	82.49%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9486	94.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.51%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	90.31%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.01%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.45%	98.95%
CHEMBL1870	P28702	Retinoid X receptor beta	86.82%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.99%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.64%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.11%	100.00%
CHEMBL2004	P48443	Retinoid X receptor gamma	82.53%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.01%	95.89%

Plants that contains it

• Cytisus scoparius
• Dioscorea polystachya
• Equisetum hyemale
• Lophophora williamsii
• Portulaca oleracea

Cross-Links

• PubChem: 16061189
• NPASS: NPC119806
• LOTUS: LTS0141142
• wikiData: Q27149334