Lycopene

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

Identification

Name
Lycopene
Accession Number
DB11231
Type
Small Molecule
Groups
Approved
Description

Lycopene is a naturally occuring red carotenoid pigment that is responsible in red to pink colors seen in tomatoes, pink grapefruit, and other foods [1]. Having a chemical formula of C40H56, lycopene is a tetraterpene assembled from eight isoprene units that are solely composed of carbon and hydrogen. Lycophene may undergo extensive isomerization that allows 1056 theoretical cis-trans configurations; however the all-trans configuration of lycopene is the most predominant isomer found in foods [1, 2] that gives the red hue. Lycopene is a non-essential human nutrient that is classified as a non-provitamin A carotenoid pigment since it lacks a terminal beta ionone ring [1] and does not mediate vitamin A activity. However lycophene is a potent antioxidant molecule that scavenges reactive oxygen species (ROS) singlet oxygen. Tomato lycopene extract is used as a color additive in food products.

Structure
Thumb
Synonyms
Not Available
External IDs
E-160D(III) / FEMA NO. 4110 / INS NO.160D(III) / INS-160D(III) / NSC-407322
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
PreQue 10Lycopene (5 mg/1) + Cholecalciferol (120 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (1 ug/1) + Doconexent (50 mg/1) + Docusate sodium (25 mg/1) + Folic Acid (.5 mg/1) + Iron (15 mg/1) + Magnesium oxide (10 mg/1) + Riboflavin (1.7 mg/1) + Selenium (7.5 ug/1) + Thiamine (1 mg/1) + Ubidecarenone (50 mg/1) + Vitamin A (1250 [iU]/1) + Vitamin C (30 mg/1) + Vitamin E (15 [iU]/1) + Zinc oxide (12.5 mg/1)TabletOralActavis Pharma Company2011-11-01Not applicableUs
Categories
UNII
SB0N2N0WV6
CAS number
502-65-8
Weight
Average: 536.888
Monoisotopic: 536.438201803
Chemical Formula
C40H56
InChI Key
OAIJSZIZWZSQBC-GYZMGTAESA-N
InChI
InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
IUPAC Name
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
SMILES
CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Lycopene.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Lycopene.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of Lycopene.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Lycopene.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Lycopene.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Lycopene.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Lycopene.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Lycopene.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Lycopene.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Lycopene.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Lycopene.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Lycopene.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Lycopene.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Lycopene.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Lycopene.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Lycopene.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Lycopene.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Lycopene.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Lycopene.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Lycopene.Approved, Investigational
Food Interactions
Not Available

References

General References
  1. Story EN, Kopec RE, Schwartz SJ, Harris GK: An update on the health effects of tomato lycopene. Annu Rev Food Sci Technol. 2010;1:189-210. doi: 10.1146/annurev.food.102308.124120. [PubMed:22129335]
  2. Shi J, Le Maguer M: Lycopene in tomatoes: chemical and physical properties affected by food processing. Crit Rev Food Sci Nutr. 2000 Jan;40(1):1-42. [PubMed:10674200]
  3. Agarwal S, Rao AV: Tomato lycopene and its role in human health and chronic diseases. CMAJ. 2000 Sep 19;163(6):739-44. [PubMed:11022591]
External Links
Human Metabolome Database
HMDB03000
KEGG Compound
C05432
PubChem Compound
446925
PubChem Substance
347827946
ChemSpider
394156
ChEBI
15948
ChEMBL
CHEMBL501174
HET
LYC
PDB Entries
1lgh

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAdenocarcinoma of the Prostate1
1CompletedPreventionProstatic Intraepithelial Neoplasia1
1, 2CompletedTreatmentChronic Periodontitis1
2CompletedPreventionBenign Prostatic Hypertrophy (BPH)1
2CompletedPreventionIntraepithelial Prostatic Neoplasia / Prostatic Neoplasms1
2CompletedTreatmentAdenocarcinoma of the Prostate / Stage I Prostate Cancer / Stage II Prostate Cancer / Stage III Prostate Cancer1
2CompletedTreatmentLichen Planus, Oral1
2CompletedTreatmentProstate Cancer1
2RecruitingSupportive CareMetastatic Colorectal Cancers / Skin Toxicities1
2Unknown StatusPreventionAneurysms / Subarachnoid Hemorrhage1
2WithdrawnPreventionTransitional Cell Carcinoma1
4CompletedTreatmentOral Lichen Planus1

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000397 mg/mLALOGPS
logP9.16ALOGPS
logP11.93ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity197.81 m3·mol-1ChemAxon
Polarizability73.69 Å3ChemAxon
Number of Rings0ChemAxon
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 carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Tetraterpenoids
Direct Parent
Carotenes
Alternative Parents
Branched unsaturated hydrocarbons / Unsaturated aliphatic hydrocarbons / Acyclic olefins
Substituents
Carotene / Branched unsaturated hydrocarbon / Unsaturated aliphatic hydrocarbon / Unsaturated hydrocarbon / Olefin / Acyclic olefin / Hydrocarbon / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
acyclic carotene (CHEBI:15948) / C40 isoprenoids (tetraterpenes), Carotenoids (C05432) / C40 isoprenoids (tetraterpenes) (LMPR01070257)

Drug created on December 03, 2015 09:51 / Updated on November 09, 2017 04:52