Violaxanthin

Identification

Generic Name
Violaxanthin
DrugBank Accession Number
DB03460
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 600.884
Monoisotopic: 600.417860283
Chemical Formula
C40H56O4
Synonyms
  • all-trans-violaxanthin
  • trans-violaxanthin
  • zeaxanthin diepoxide
External IDs
  • CHEBI:35288
  • E 161E

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Oxepanes / Secondary alcohols / Cyclic alcohols and derivatives / Oxacyclic compounds / Epoxides / Dialkyl ethers / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Cyclic alcohol / Dialkyl ether / Ether / Hydrocarbon derivative / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound / Oxacycle
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
violaxanthin (CHEBI:35288) / C40 isoprenoids (tetraterpenes), Carotenoids (C08614) / C40 isoprenoids (tetraterpenes) (LMPR01070282)
Affected organisms
Not Available

Chemical Identifiers

UNII
51C926029A
CAS number
126-29-4
InChI Key
SZCBXWMUOPQSOX-WVJDLNGLSA-N
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
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-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
SMILES
C\C(\C=C\C=C(/C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C

References

General References
Not Available
KEGG Compound
C08614
PubChem Compound
448438
PubChem Substance
46505440
ChemSpider
395237
ChEBI
35288
ZINC
ZINC000008221270
PDBe Ligand
XAT
Wikipedia
Violaxanthin
PDB Entries
1rwt / 2bhw / 3jcu / 3pl9 / 4xk8 / 5l8r / 5xnl / 5xnm / 5xnn / 5xno
show 60 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.000568 mg/mLALOGPS
logP8.33ALOGPS
logP7.26Chemaxon
logS-6ALOGPS
pKa (Strongest Acidic)14.84Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area62.22 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity192.33 m3·mol-1Chemaxon
Polarizability74.48 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9722
Blood Brain Barrier+0.5934
Caco-2 permeable+0.6156
P-glycoprotein substrateSubstrate0.7045
P-glycoprotein inhibitor IInhibitor0.5269
P-glycoprotein inhibitor IINon-inhibitor0.9358
Renal organic cation transporterNon-inhibitor0.9028
CYP450 2C9 substrateNon-substrate0.8207
CYP450 2D6 substrateNon-substrate0.8422
CYP450 3A4 substrateSubstrate0.6465
CYP450 1A2 substrateNon-inhibitor0.8519
CYP450 2C9 inhibitorNon-inhibitor0.8314
CYP450 2D6 inhibitorNon-inhibitor0.9441
CYP450 2C19 inhibitorNon-inhibitor0.7199
CYP450 3A4 inhibitorNon-inhibitor0.8778
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8434
Ames testAMES toxic0.5928
CarcinogenicityNon-carcinogens0.8747
BiodegradationNot ready biodegradable0.9867
Rat acute toxicity2.7889 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9777
hERG inhibition (predictor II)Non-inhibitor0.9003
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0000091000-99e7934161c39c74ec9c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0100190000-917ff9d97be8a5f83909
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0203490000-d76259ff6107196048d1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-0121392000-ab1ae2c3c839cb6583b6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f83-0916140000-f8a37b0c7aab56379c7e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0015950000-1ea64234b961b0397de6
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-328.0952692
predicted
DarkChem Lite v0.1.0
[M-H]-253.71169
predicted
DeepCCS 1.0 (2019)
[M+H]+330.9152692
predicted
DarkChem Lite v0.1.0
[M+H]+255.98866
predicted
DeepCCS 1.0 (2019)
[M+Na]+327.4142692
predicted
DarkChem Lite v0.1.0
[M+Na]+262.31094
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52