Astaxanthin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Astaxanthin
Accession Number
DB06543
Type
Small Molecule
Groups
Investigational
Description

Astaxanthin is a keto-carotenoid in the terpenes class of chemical compounds. It is classified as a xanthophyll but it is a carotenoid with no vitamin A activity. It is present in most red-coloured aquatic organisms. Astaxanthin has shown to mediate anti-oxidant and anti-inflammatory actions. It may be found in fish feed or some animal food as a color additive.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
AstaFactor
Categories
UNII
8XPW32PR7I
CAS number
472-61-7
Weight
Average: 596.852
Monoisotopic: 596.386560154
Chemical Formula
C40H52O4
InChI Key
MQZIGYBFDRPAKN-UWFIBFSHSA-N
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
IUPAC Name
(6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C

Pharmacology

Indication

Investigated for use/treatment in eye disorders/infections, cancer/tumors (unspecified), and asthma.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNF-kappa-B inhibitor alphaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1,2,6,7-3H)TestosteroneThe therapeutic efficacy of Astaxanthin can be increased when used in combination with (1,2,6,7-3H)Testosterone.
(R)-warfarinThe risk or severity of bleeding can be increased when Astaxanthin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Astaxanthin is combined with (S)-Warfarin.
1-TestosteroneThe therapeutic efficacy of Astaxanthin can be increased when used in combination with 1-Testosterone.
18-methyl-19-nortestosteroneThe therapeutic efficacy of Astaxanthin can be increased when used in combination with 18-methyl-19-nortestosterone.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Astaxanthin is combined with 4-hydroxycoumarin.
4-HydroxytestosteroneThe therapeutic efficacy of Astaxanthin can be increased when used in combination with 4-Hydroxytestosterone.
5beta-dihydrotestosteroneThe therapeutic efficacy of Astaxanthin can be increased when used in combination with 5beta-dihydrotestosterone.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Astaxanthin.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Astaxanthin.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0002204
KEGG Compound
C08580
PubChem Compound
5281224
PubChem Substance
347827776
ChemSpider
4444636
ChEBI
40968
ChEMBL
CHEMBL1255871
HET
AXT
Wikipedia
Astaxanthin
PDB Entries
1gka

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentNPDR - Non Proliferative Diabetic Retinopathy / Type 2 Diabetes Mellitus1
Not AvailableUnknown StatusBasic ScienceBody Temperature Regulation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000667 mg/mLALOGPS
logP7.4ALOGPS
logP8.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.98 m3·mol-1ChemAxon
Polarizability73.77 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Tetraterpenoids
Direct Parent
Xanthophylls
Alternative Parents
Cyclohexenones / Secondary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Xanthophyll / Cyclohexenone / Cyclic ketone / Secondary alcohol / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
carotenone, carotenol (CHEBI:40968) / C40 isoprenoids (tetraterpenes), Carotenoids (C08580) / C40 isoprenoids (tetraterpenes) (LMPR01070263)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Inhibits the activity of dimeric NF-kappa-B/REL complexes by trapping REL dimers in the cytoplasm through masking of their nuclear localization signals. On cellular stimulation by immune and proinf...
Gene Name
NFKBIA
Uniprot ID
P25963
Uniprot Name
NF-kappa-B inhibitor alpha
Molecular Weight
35608.65 Da
References
  1. Lee SJ, Bai SK, Lee KS, Namkoong S, Na HJ, Ha KS, Han JA, Yim SV, Chang K, Kwon YG, Lee SK, Kim YM: Astaxanthin inhibits nitric oxide production and inflammatory gene expression by suppressing I(kappa)B kinase-dependent NF-kappaB activation. Mol Cells. 2003 Aug 31;16(1):97-105. [PubMed:14503852]

Drug created on March 19, 2008 10:36 / Updated on November 02, 2018 06:17