Astaxanthin

Details

• Internal ID: e5651156-1a4f-4704-81e3-c0a2f76efdd5
• 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-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-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)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)O)(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)/C)/C
• InChI: InChI=1S/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36-/m0/s1
• InChI Key: MQZIGYBFDRPAKN-UWFIBFSHSA-N
• Popularity: 5,591 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₂O₄
• Molecular Weight: 596.80 g/mol
• Exact Mass: 596.38656014 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 10.30
• Atomic LogP (AlogP): 8.91
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• 472-61-7
• Ovoester
• all-trans-Astaxanthin
• AstaREAL
• 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione
• Astaxanthine
• BioAstin
• (3S,3'S)-Astaxanthin
• trans-Astaxanthin
• Astaxanthin, (3S,3'S)-
• (3S,3'S)-all-trans-Astaxanthin
• 8XPW32PR7I
• 3,3'-Dihydroxy-beta-carotene-4,4'-dione
• (3S,3'S)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione
• CHEBI:40968
• NSC-635689
• (6S,6'S)-3,3'-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(6-hydroxy-2,4,4-trimethylcyclohex-2-enone)
• .beta.,.beta.-Carotene-4,4'-dione, 3,3'-dihydroxy-, (3S,3'S)-
• Algae Haematococcus pluvialis
• Natupink
• AstaXin
• Carophyll Pink
• Lucantin Pink
• BioAstin oleoresin
• (6S)-6-Hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone
• Astaxanthin (6CI)
• Astaxanthin, all-trans-
• (6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-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
• UNII-8XPW32PR7I
• astaxantin
• CCRIS 7118
• HSDB 7468
• EINECS 207-451-4
• NSC 635689
• 3S,3'S-Astaxanthin
• Astaxanthin, all-trans-, (3S,3'S)-
• Astaxanthin, 5% active
• ASTAXANTHIN [MI]
• b-Carotene-4,4'-dione
• ASTAXANTHIN [HSDB]
• ASTAXANTHIN [INCI]
• ASTAXANTHIN [VANDF]
• beta-Carotene-4,4'-dione
• ASTAXANTHIN [MART.]
• SCHEMBL20047
• ASTAXANTHIN [USP-RS]
• ASTAXANTHIN [WHO-DD]
• E161j
• CHEMBL1255871
• Astaxanthin, >=98% (HPLC)
• E 161j
• DTXSID00893777
• all-trans-(3S,3'S)-astaxanthin
• 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione, (3S,3'S)-
• HMS3885C08
• BCP05821
• HY-B2163
• LMPR01070263
• MFCD00672621
• s3834
• AKOS015841055
• AKOS015895756
• AC-8760
• BCP9000329
• CCG-270185
• DB06543
• all-trans-Astaxanthin, analytical standard
• AS-14095
• CS-0020413
• C08580
• M01303
• 3,3'-dihydroxy-4,4'-diketo-beta,beta-carotene
• A827177
• Q413740
• Q-200655
• 3,3'-DIHYDROXY-4,4'-DIKETO-.BETA.-CAROTENE
• all-trans-3,3'-dihydroxy-b-Carotene-4,4'-dione (8CI)
• .beta.-Carotene-4,4'-dione, 3,3'-dihydroxy-, all-trans-
• 3-(4,6-Dimethyl-2-oxo-2H-pyrimidin-1-yl)-propionicacid
• all-trans-3,3'-dihydroxy-beta-Carotene-4,4'-dione (8CI)
• 3,3'-Dihydroxy-.beta.,.beta.-carotene-4,4'-dione, (3S,3'S)-
• (3S,3'S)-3,3'-DIHYDROXY-.BETA.,.BETA.-CAROTENE-4,4'-DIONE
• 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione;(S)-6-hydroxy-3-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-((S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-enyl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl)-2,4,4-trimethylcyclohex-2-enone;

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	-	0.8130	81.30%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7988	79.88%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.8207	82.07%
OATP1B3 inhibitior	+	0.9507	95.07%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8061	80.61%
P-glycoprotein substrate	-	0.8459	84.59%
CYP3A4 substrate	+	0.5909	59.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.8345	83.45%
CYP2C9 inhibition	-	0.8936	89.36%
CYP2C19 inhibition	-	0.8316	83.16%
CYP2D6 inhibition	-	0.9140	91.40%
CYP1A2 inhibition	-	0.9253	92.53%
CYP2C8 inhibition	-	0.9207	92.07%
CYP inhibitory promiscuity	-	0.8676	86.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8028	80.28%
Carcinogenicity (trinary)	Non-required	0.5877	58.77%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9039	90.39%
Skin irritation	-	0.6953	69.53%
Skin corrosion	-	0.9530	95.30%
Ames mutagenesis	-	0.6308	63.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.8031	80.31%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7809	78.09%
skin sensitisation	+	0.7440	74.40%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.7975	79.75%
Acute Oral Toxicity (c)	III	0.6658	66.58%
Estrogen receptor binding	+	0.8431	84.31%
Androgen receptor binding	+	0.8450	84.50%
Thyroid receptor binding	+	0.7134	71.34%
Glucocorticoid receptor binding	+	0.8549	85.49%
Aromatase binding	-	0.5166	51.66%
PPAR gamma	+	0.7448	74.48%
Honey bee toxicity	-	0.8603	86.03%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9496	94.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.05%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.38%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	90.33%	94.75%
CHEMBL1870	P28702	Retinoid X receptor beta	89.73%	95.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.47%	96.09%
CHEMBL2004	P48443	Retinoid X receptor gamma	87.16%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.39%	100.00%
CHEMBL2061	P19793	Retinoid X receptor alpha	83.71%	91.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.23%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.02%	92.94%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.90%	95.50%
CHEMBL2581	P07339	Cathepsin D	81.26%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.85%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.71%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.34%	99.23%
CHEMBL3572	P11597	Cholesteryl ester transfer protein	80.07%	92.67%

Plants that contains it

• Metasequoia glyptostroboides

Cross-Links

• PubChem: 5281224
• LOTUS: LTS0012737
• wikiData: Q413740