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Details

Stereochemistry ACHIRAL
Molecular Formula C40H56
Molecular Weight 536.8726
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 11
Charge 0

SHOW SMILES / InChI
Structure of LYCOPENE

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

InChI

InChIKey=OAIJSZIZWZSQBC-GYZMGTAESA-N
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+

HIDE SMILES / InChI
Molecular Formula C40H56
Molecular Weight 536.8726
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 11
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.fda.gov/ohrms/dockets/dockets/04q0201/04q-0201-qhc0002-04-Section-B-02-vol1.pdf http://www.rxlist.com/lycopene-page2/supplements.htm

Lycopene is the fat-soluble pigment that gives tomatoes, watermelon, pink grapefruit, and other foods their red color. Bioavailability of lycopene is enhanced in the presence of lipids and thermal processing. Lycopene accounts for about 50% of the carotenoids found in human serum and is among the major carotenoids present in human milk. The antioxidant activity of lycopene and its use in cancer prevention and cardiovascular disease have been widely documented. The scientific literature documents some adverse reactions, such as diarrhea, dyspepsia, gas, nausea, and vomiting. One trial documented a cancer-related hemorrhage in a patient taking lycopene, although causality is unclear. Lycopene interacts with some cancer chemotherapy agents, as well as with ciprofloxacin and olestra.

CNS Activity

CNS Active
3913
Curator's Comment: Lycopene was shown to cross the blood brain barrier and be present in the central nervous system in low concentrations. Deficiency of a series of anti-oxidation nutrients including lycopene is related to such neurodegenerative diseases as Parkinson’s disease, vascular dementia, Alzheimer disease, etc.

Originator

Willstätter, R.|Escher, H.H.
1
Sources: www.drugfuture.com/chemdata/lycopene.html
Curator's Comment: The molecular formula (C40H56) was established in 1910.

Approval Year

2007
205
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase III
656
Ateronon

Approved Use

Unknown
Preventing
Phase III
656
Ateronon

Approved Use

Unknown
Preventing
Phase III
656
Ateronon

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
cis-trans isomers of lycopene and beta-carotene in human serum and tissues.
1992 Apr
Skin lycopene is destroyed preferentially over beta-carotene during ultraviolet irradiation in humans.
1995 Jul
The potential role of lycopene for human health.
1997 Apr
Intestinal absorption of lycopene from different matrices and interactions to other carotenoids, the lipid status, and the antioxidant capacity of human plasma.
1999 Jun
Lymphocyte lycopene concentration and DNA protection from oxidative damage is increased in women after a short period of tomato consumption.
2000 Feb
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.
2000 Jan-Feb
Lycopene and cardiovascular disease.
2000 Jun
Antioxidant and pro-oxidant effects of lycopene in comparison with beta-carotene on oxidant-induced damage in Hs68 cells.
2000 Nov
Summary of safety studies conducted with synthetic lycopene.
2003 Apr
Lycopene in serum, skin and adipose tissues after tomato-oleoresin supplementation in patients undergoing haemorrhoidectomy or peri-anal fistulotomy.
2003 Oct
Lycopene and vitamin E interfere with autocrine/paracrine loops in the Dunning prostate cancer model.
2004 Jun
Noninvasive selective detection of lycopene and beta-carotene in human skin using Raman spectroscopy.
2004 Mar-Apr
Supplementation with tomato-based products increases lycopene, phytofluene, and phytoene levels in human serum and protects against UV-light-induced erythema.
2005 Jan
Inhibitory effects of lycopene on in vitro platelet activation and in vivo prevention of thrombus formation.
2005 Oct
Lycopene inhibition of IGF-induced cancer cell growth depends on the level of cyclin D1.
2006 Aug
Gene signature of breast cancer cell lines treated with lycopene.
2006 Jul
Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells.
2006 Jul
Oral administration of lycopene reverses cadmium-suppressed body weight loss and lipid peroxidation in rats.
2007 Aug
Gene expression profiling of aging in multiple mouse strains: identification of aging biomarkers and impact of dietary antioxidants.
2009 Aug
Studies on the protective role of lycopene against polychlorinated biphenyls (Aroclor 1254)-induced changes in StAR protein and cytochrome P450 scc enzyme expression on Leydig cells of adult rats.
2009 Jan
Differential effects of several phytochemicals and their derivatives on murine keratinocytes in vitro and in vivo: implications for skin cancer prevention.
2009 Jun
Dietary lycopene and tomato extract supplementations inhibit nonalcoholic steatohepatitis-promoted hepatocarcinogenesis in rats.
2010 Apr 15
Neurohepatic toxicity of subacute manganese chloride exposure and potential chemoprotective effects of lycopene.
2012 Jan
An interaction between carotene-15,15'-monooxygenase expression and consumption of a tomato or lycopene-containing diet impacts serum and testicular testosterone.
2012 Jul 15
Modulatory effect of lycopene on deltamethrin-induced testicular injury in rats.
2013 Apr
Protection against chemotaxis in the anti-inflammatory effect of bioactives from tomato ketchup.
2014
Lycopene protects against acute zearalenone-induced oxidative, endocrine, inflammatory and reproductive damages in male mice.
2015 Mar 25
Patents

Patents

05166445
1
05208381
1
05973179
1
06509029
1
07056525
1
07928266
1
08293946
1

Sample Use Guides

In Vivo Use Guide
As a pure compound it has been studied in clinical trials at dosages of 13 to 75 mg/day. Dosage guidelines from manufacturers ranging from 10 to 30 mg taken twice daily with meals. For example, as an antioxidant, lycopene has been taken in doses of 6.5, 15, and 30 milligrams daily for eight weeks. To treat asthma caused by exercise, 30 milligrams of lycopene has been taken daily for one week.
Route of Administration: Oral
In Vitro Use Guide
The lycopene showed significant antioxidant activity against nitric oxide radical with IC50 value of 57.879 ug/ml and antioxidant activity against reducing power method with IC50 value of 45.609 ug/ml respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:44 UTC 2023
Edited
by admin
on Fri Dec 15 15:56:44 UTC 2023
Record UNII
SB0N2N0WV6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LYCOPENE
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
INS-160D(III)
Code English
TOMAT-O-RED
Common Name English
TOMATO LYCOPENE [FHFI]
Common Name English
(ALL-TRANS)-LYCOPENE
Common Name English
LYCORED
Common Name English
LYCOPENE [MI]
Common Name English
LYCOPENE [MART.]
Common Name English
LYCOPENE PREPARATION [USP-RS]
Common Name English
LYCOPENE EXTRACT FROM TOMATO [FCC]
Common Name English
Solanorubin
Common Name English
(ALL-E)-2,6,10,14,19,23,27,31-OCTAMETHYL-2,6,8,10,12,14,16,18,20,22,24,26,30-DOTRIACONTATRIDECAENE
Common Name English
(ALL-E)-LYCOPENE (CONSTITUENT OF LYCOPENE AND TOMATO EXTRACT CONTAINING LYCOPENE) [DSC]
Common Name English
FEMA NO. 4110
Code English
CI 75125 [INCI]
Common Name English
LYCOPENE FROM BLAKESLEA TRISPORA [FCC]
Common Name English
NSC-407322
Code English
LYCOPENE [INCI]
Common Name English
BLAKESLEA TRISPORA
Common Name English
ATERONON
Brand Name English
REDIVIVO
Common Name English
Lycopene [WHO-DD]
Common Name English
LYCOPENE FROM BLAKESLEA TRISPORA
FCC  
Common Name English
E-160D(III)
Code English
(ALL-E)-LYCOPENE
Common Name English
INS NO.160D(III)
Code English
LYCOPENE EXTRACT FROM TOMATO
FCC  
Common Name English
MEXORYL SAQ
Common Name English
LYCOPENE [VANDF]
Common Name English
AEC LYCOPENE
Brand Name English
CI 75125
INCI  
INCI  
Official Name English
Classification Tree Code System Code
JECFA EVALUATION INS-160D(III)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
DSLD 164 (Number of products:1777)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
LOINC 27075-1
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DSLD 1297 (Number of products:1)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
CODEX ALIMENTARIUS (GSFA) INS-160D(III)
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
NCI_THESAURUS C68307
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
Code System Code Type Description
FDA UNII
SB0N2N0WV6
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
CHEBI
15948
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PRIMARY
ECHA (EC/EINECS)
207-949-1
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PRIMARY
WIKIPEDIA
LYCOPENE
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
PUBCHEM
446925
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PRIMARY
SMS_ID
100000088233
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PRIMARY
DAILYMED
SB0N2N0WV6
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
CAS
502-65-8
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PRIMARY
NSC
407322
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
NCI_THESAURUS
C2226
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PRIMARY
RS_ITEM_NUM
1370881
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PRIMARY
MESH
C015329
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PRIMARY
DRUG CENTRAL
4617
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PRIMARY
EPA CompTox
DTXSID2046593
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
EVMPD
SUB21639
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
DRUG BANK
DB11231
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY
MERCK INDEX
m6951
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY Merck Index
RXCUI
29008
Created by admin on Fri Dec 15 15:56:45 UTC 2023 , Edited by admin on Fri Dec 15 15:56:45 UTC 2023
PRIMARY RxNorm
Related Record Type Details
Structure of BETA CAROTENE
CONSTITUENT ALWAYS PRESENT -> PARENT
Related Record Type Details
Structure of LYCOPENE
ACTIVE MOIETY
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