dibenzo(a,l)pyrene profile

Dibenzo(a,l)pyrene (DB[a,l]P) is a potent polycyclic aromatic hydrocarbon (PAH) that is formed during incomplete combustion of organic materials. It is a known human carcinogen that can cause lung cancer, skin cancer, and other types of cancer. DB[a,l]P is present in various environmental sources such as coal tar, diesel exhaust, and cigarette smoke. It is also found in food, particularly grilled or smoked meats. Research on DB[a,l]P focuses on its carcinogenic properties, its mechanisms of action in inducing cancer, and its potential impact on human health. Studies aim to understand how DB[a,l]P interacts with DNA, leading to mutations and uncontrolled cell growth. This information is crucial for developing strategies to mitigate the risk of exposure to DB[a,l]P and prevent related health issues.'

dibenzo(a,l)pyrene: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	9119
CHEBI ID	35861
MeSH ID	M0123131

Synonym
4,6,7-dibenzpyrene
db(a,l)p
wln: l d66 k666 b6 2ab a & j
ba 51-090462
dibenzo[a,l]pyrene
1,9,10-dibenzopyrene
dibenzo[a,d]pyrene
1,3,4-dibenzpyrene
191-30-0
dibenzo[d,f,p]chrysene
1,4-dibenzopyrene
nsc90324
nsc-90324
dibenzo(d,e,f,p)chrysene
1,2,9,10-dibenzopyrene
1,2,3,4-dibenzpyrene
CHEBI:35861
naphtho[1,2,3,4-pqr]tetraphene
1,2:9,10-dibenzopyrene
2,3:4,5-dibenzopyrene
4,5,6,7-dibenzpyrene
einecs 205-886-4
dibenzo(def,p)chrysene
ccris 210
dibenzo(a,d)pyrene
hsdb 4029
brn 2054068
nsc 90324
dibenzo(a,l)pyrene
dibenzo[def,p]chrysene
1,2:3,4-dibenzopyrene
FT-0666414
C19174
AKOS024319580
unii-g3x629ve4a
g3x629ve4a ,
2,3:4,5-dibenzpyrene
dibenzo(a,l)pyrene [iarc]
dibenzo(a,l)pyrene [hsdb]
DTXSID9059753
2-decyldodecanoicacid
4,5:6,7-dibenzpyrene
JNTHRSHGARDABO-UHFFFAOYSA-N
dibenz[a,l]pyrene
dibenzo[a,l]pyrene, bcr(r) certified reference material
dibenzo[a,l]pyrene, vial of 25 mg
dibenzo[a,l]pyrene 10 microg/ml in acetonitrile
dibenzo[a,l]pyrene 10 microg/ml in cyclohexane
J-012363
Q26840756
hexacyclo[10.10.2.02,7.08,24.015,23.017,22]tetracosa-1(23),2,4,6,8,10,12(24),13,15,17,19,21-dodecaene

Excerpt	Reference	Relevance
" Despite significant public health concern, physiologically based pharmacokinetic (PBPK) modeling efforts for PAHs have so far been limited to naphthalene, plus simpler PK models for pyrene, nitropyrene, and benzo[a]pyrene (B[a]P)."	( Preliminary physiologically based pharmacokinetic models for benzo[a]pyrene and dibenzo[def,p]chrysene in rodents. Amin, SG; Anderson, KA; Corley, RA; Crowell, SR; Krishnegowda, G; Sharma, AK; Soelberg, JJ; Williams, DE, 2011)	0.37
" We present pharmacokinetic data of DBC in pregnant and nonpregnant mice."	( Impact of pregnancy on the pharmacokinetics of dibenzo[def,p]chrysene in mice. Amin, S; Baird, WM; Corley, RA; Crowell, SR; Sadler, NC; Sharma, AK; Soelberg, JJ; Williams, DE; Wright, AT, 2013)	0.39
" The plasma Cmax was 68."	( Human in Vivo Pharmacokinetics of [(14)C]Dibenzo[def,p]chrysene by Accelerator Mass Spectrometry Following Oral Microdosing. Corley, RA; Crowell, S; Garrard, M; Madeen, E; Malfatti, M; McQuistan, TJ; Ognibene, T; Sudakin, D; Turteltaub, K; Williams, DE, 2015)	0.42
" After 24 h, the stomach had the highest radioactivity followed by the intestine and the liver; however, after 1 week, levels of the radioactivity in these organs were the lowest among tissues examined including the ovary and liver; the pharmacokinetic analysis of DBP was conducted using a one compartment open model."	( Tissue Distribution, Excretion and Pharmacokinetics of the Environmental Pollutant Dibenzo[def,p]chrysene in Mice. Aliaga, C; Amin, S; Awad, AS; Chen, KM; El-Bayoumy, K; Gowda, K; Sun, YW, 2015)	0.42

Excerpt	Reference	Relevance
" These data suggest that the transport of AFB(1) and DBP can be inhibited by CHL, which supports a model of direct binding in the intestinal tract of CHL to these carcinogens with resultant reduction of bioavailability as one mechanism of action as a cancer chemopreventive agent."	( Effects of chlorophyllin on transport of dibenzo(a, l)pyrene, 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine, and aflatoxin B(1) across Caco-2 cell monolayers. Gray, JE; Mata, JE; Rodriguez-Proteau, R; Williams, DE; Yu, Z, 2004)	0.32
" The bioavailability of DBP to fetal target tissue was demonstrated by assessing DNA covalent adduction with a (33)P-post-labeling assay."	( Indole-3-carbinol in the maternal diet provides chemoprotection for the fetus against transplacental carcinogenesis by the polycyclic aromatic hydrocarbon dibenzo[a,l]pyrene. Albershardt, DJ; Bailey, GS; Baird, WM; Fischer, KA; Krueger, SK; Löhr, CV; Louderback, MA; Mahadevan, B; Pereira, CB; Williams, DE; Yu, Z, 2006)	0.33
" Induction of Cytochrome P450 (Cyp)1b1 in maternal liver may reduce bioavailability of DBP to the fetus as a mechanism of chemoprevention."	( Chemoprevention of dibenzo[a,l]pyrene transplacental carcinogenesis in mice born to mothers administered green tea: primary role of caffeine. Castro, DJ; Dashwood, RH; Fischer, KA; Giovanini, JN; Löhr, CV; Orner, GA; Pereira, CB; Williams, DE; Yu, Z, 2008)	0.35

Excerpt	Relevance	Reference
" Dose-response studies were conducted at low doses in mouse skin by initiation-promotion and repeated application to compare its activity to that of 7,12-dimethylbenz[a]anthracene (DMBA), benzo[a]pyrene (B[a]P), DB[a,l]P-8,9-dihydrodiol and DB[a,l]P-11,12-dihydrodiol."	( Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene at low doses in mouse skin. Cavalieri, EL; Higginbotham, S; Johansson, SL; RamaKrishna, NV; Rogan, EG, 1993)	0.29
" The bioavailability of I3C was determined by dosing a subset of pregnant mice with [(14)C]-I3C."	( Indole-3-carbinol in the maternal diet provides chemoprotection for the fetus against transplacental carcinogenesis by the polycyclic aromatic hydrocarbon dibenzo[a,l]pyrene. Albershardt, DJ; Bailey, GS; Baird, WM; Fischer, KA; Krueger, SK; Löhr, CV; Louderback, MA; Mahadevan, B; Pereira, CB; Williams, DE; Yu, Z, 2006)	0.33
" DBP treatment alone produced a logit incidence versus log [DBP] dose-response curve in stomach that was linear; CHL co-treatment provided dose-dependent tumor inhibition which ranged from 30 to 68% and was predictable from the adduct response."	( The importance of carcinogen dose in chemoprevention studies: quantitative interrelationships between, dibenzo[a,l]pyrene dose, chlorophyllin dose, target organ DNA adduct biomarkers and final tumor outcome. Bailey, GS; Hendricks, JD; Kensler, TW; Pereira, C; Pratt, MM; Reddy, AP, 2007)	0.34
" Dose-response and chemopreventive mechanisms for tomatine protection remain to be examined."	( Protective effect of dietary tomatine against dibenzo[a,l]pyrene (DBP)-induced liver and stomach tumors in rainbow trout. Bailey, GS; Friedman, M; Hendricks, JD; McQuistan, T; Pereira, C, 2007)	0.34
" In this study, we investigated the effect of two dosing regimens on the mutagenicity of DB[a,l]P and B[a]P in vivo using the Big Blue(R) transgenic mouse system."	( Mutations induced by benzo[a]pyrene and dibenzo[a,l]pyrene in lacI transgenic B6C3F1 mouse lung result from stable DNA adducts. George, MH; Leavitt, SA; Moore, T; Ross, JA, 2008)	0.35
" The degree of protection by CHL, compared with controls dosed with DBP in tricaprylin (TCP) as the vehicle, was less marked, but still significant."	( Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesis. Bailey, GS; Castro, DJ; Dashwood, RH; Fischer, KA; Löhr, CV; Waters, KM; Webb-Robertson, BJ; Williams, DE, 2009)	0.35
" Mice heterozygous for the disrupted cyp1b1 allele were used to examine the effect of cyp1b1 gene dosage on DBP transplacental carcinogenesis."	( Fetal mouse Cyp1b1 and transplacental carcinogenesis from maternal exposure to dibenzo(a,l)pyrene. Baird, WM; Castro, DJ; Fischer, KA; Giovanini, J; Gonzalez, FJ; Krueger, SK; Löhr, CV; Pereira, CB; Williams, DE; Yu, Z, 2008)	0.57
" We used rainbow trout, an animal model well-suited to ultralow-dose carcinogenesis research, to explore dose-response down to a targeted 10 excess liver tumors per 10000 animals (ED(001))."	( Nonlinear cancer response at ultralow dose: a 40800-animal ED(001) tumor and biomarker study. Bailey, GS; Baird, W; Harttig, U; Hendricks, JD; Orner, GA; Pereira, CB; Reddy, AP; Spitsbergen, JM; Swenberg, JA; Williams, DE, 2009)	0.35
" Trout have critical and unique advantages allowing for cancer studies with 40,000 animals to determine dose-response at levels orders of magnitude lower than possible in rodents."	( The rainbow trout liver cancer model: response to environmental chemicals and studies on promotion and chemoprevention. Williams, DE, 2012)	0.38
" This finding questions the human relevance of chemoprevention studies carried out at high carcinogen doses that are not proven to lie within a linear, or at least monotonic, endpoint dose-response range."	( Cancer chemoprevention by dietary chlorophylls: a 12,000-animal dose-dose matrix biomarker and tumor study. Bailey, GS; Dashwood, RH; Hendricks, JD; McQuistan, TJ; Pereira, CB; Pratt, MM; Simonich, MT; Williams, DE, 2012)	0.38
" [(14)C]-DBC (GD 17) dosing revealed transplacental distribution to fetal tissues at 10-fold lower concentrations than in paired maternal tissue and residual [(14)C] 3weeks post-dose."	( Transplacental carcinogenesis with dibenzo[def,p]chrysene (DBC): timing of maternal exposures determines target tissue response in offspring. Baird, WM; Castro, DJ; Corley, RA; Löhr, CV; Matzke, MM; Shorey, LE; Siddens, LK; Waters, KM; Williams, DE, 2012)	0.38
" It was also found that as with DMBA, DBC produced a persistent immunosuppression, which lasted for at least 4 wk following dosing with a novel pill method for self-administration of DBC."	( Dibenzo[def,p]chrysene (DBC) suppresses antibody formation in spleen cells following oral exposures of mice. Burchiel, SW; Lauer, FT; Walker, MK, 2013)	0.39

Role	Description
mutagen	An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
human metabolite	Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
ortho- and peri-fused polycyclic arene
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (2.44)	18.7374
1990's	34 (27.64)	18.2507
2000's	45 (36.59)	29.6817
2010's	38 (30.89)	24.3611
2020's	3 (2.44)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	2 (1.56%)	5.53%
Reviews	1 (0.78%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	125 (97.66%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
adenine [no description available]	2.73	3	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.02	1	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.98	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	4.67	27	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	1.99	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
caffeine [no description available]	2.47	2	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
3,3'-diindolylmethane 3,3'-diindolylmethane: anti-inflammatory from edible cruciferous vegetables; a cytochrome P-450 antagonist	2.11	1	0	indoles	antineoplastic agent; P450 inhibitor
ethoxyresorufin ethoxyresorufin: structure	2.03	1	0	phenoxazine
indole-3-carbinol indole-3-carbinol: occurs in edible cruciferous vegetables. indole-3-methanol : An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.	4.08	4	0	indolyl alcohol	antineoplastic agent; plant metabolite
methoxyamine methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure	2.02	1	0	organooxygen compound
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.08	1	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	3.17	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	2.1	1	0	ortho-fused polycyclic arene	mutagen
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.04	1	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	3.09	5	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	2	1	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	2.72	3	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
sym-trinitrobenzene Trinitrobenzenes: Benzene derivatives which are substituted with three nitro groups in any position.. 1,3,5-trinitrobenzene : A trinitrobenzene in which each of the nitro groups is meta- to the other two.	2.08	1	0	trinitrobenzene	explosive
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.41	2	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.04	1	0	catechin	antioxidant; plant metabolite
dibenzo(a,i)pyrene [no description available]	2	1	0	ortho- and peri-fused polycyclic arene
anthanthrene [no description available]	1.97	1	0	ortho- and peri-fused polycyclic arene
benzo(g)chrysene benzo(g)chrysene: structure given in first source	1.99	1	0
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	1.98	1	0	ortho- and peri-fused polycyclic arene
picene picene: structure given in first source. picene : An ortho-fused polycyclic arene consisting of five fused benzene rings. It is obtained during the distillation of petroleum.	2	1	0	ortho-fused polycyclic arene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.41	2	0	diazine; pyrazines	Daphnia magna metabolite
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	3.17	1	0	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
2'-deoxy-5'-adenosine monophosphate 2'-deoxy-5'-adenosine monophosphate: RN given refers to parent cpd. 2'-deoxyadenosine 5'-monophosphate : A purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase.	2	1	0	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-monophosphate	fundamental metabolite
2'-deoxyadenosine 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source	2.11	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.02	1	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	2.02	1	0
5-methylchrysene 5-methylchrysene: methylchrysenes in tobacco smoke are suspected to contribute to tumorigenicity of this inhalant; RN given refers to unlabeled cpd; structure	2.06	1	0	carbopolycyclic compound
n'-nitrosonornicotine N'-nitrosonornicotine: structure; a potent carcinogen in laboratory animals	2.21	1	0	pyridines; pyrrolidines
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.42	2	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	1.99	1	0
7,8-dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide: 7,8,8a,9a-Tetrahydrobenzo(10,11)chryseno (3,4-b)oxirene-7,8-diol. A benzopyrene derivative with carcinogenic and mutagenic activity.	2.7	3	0	epoxide	intercalator
oltipraz oltipraz : A 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively.	2.41	2	0	1,2-dithiole; pyrazines	angiogenesis modulating agent; antimutagen; antineoplastic agent; antioxidant; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; neurotoxin; protective agent; schistosomicide drug
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.04	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
1,2-dithiol-3-thione 1,2-dithiol-3-thione: has antioxidant activity; structure given in first source	2.41	2	0	1,2-dithiole
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	2.11	1	0	abietane diterpenoid	anticoronaviral agent
dibenzo(a,l)pyrene 11,12-dihydrodiol dibenzo(a,l)pyrene 11,12-dihydrodiol: structure given in first source	3.1	5	0
benzo(g)chrysene-11,12-dihydrodiol-13,14-epoxide benzo(g)chrysene-11,12-dihydrodiol-13,14-epoxide: structure given in first source; RN given refers to (7alpha,6beta,8abeta,9abeta)-isomer	1.98	1	0
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	3.17	1	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	2.11	1	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant metabolite
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	3.54	2	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.11	1	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.11	1	0	stilbene
6-thioguanosine 6-thioguanosine: RN given refers to cpd without isomeric designation	2.25	1	0	purine nucleoside
11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydrodibenzo(a,l)pyrene 11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydrodibenzo(a,l)pyrene: RN refers to (alpha,beta,beta,beta)-stereoisomer; structure in first source	3.1	5	0
ku 55933 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one: specific inhibitor of the ataxia-telangiectasia mutated kinase ATM; structure in first source	2.11	1	0
nu 7026 2-(morpholin-4-yl)benzo(h)chromen-4-one: a radiosensitizing agent that inhibits DNA-dependent protein kinase; structure in first source	2.57	2	0	organic heterotricyclic compound; organooxygen compound
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	4.13	3	1	chlorophyll; methyl ester	cofactor
tomatine Tomatine: An alkaloid that occurs in the extract of leaves of wild tomato plants. It has been found to inhibit the growth of various fungi and bacteria. It is used as a precipitating agent for steroids. (From The Merck Index, 11th ed). tomatine : A steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose.	2.03	1	0
deoxyguanosine [no description available]	2.1	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2'-deoxyguanosine 5'-phosphate 2'-deoxyguanosine 5'-phosphate: RN given refers to parent cpd.. 2'-deoxyguanosine 5'-monophosphate : A purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase.	2	1	0	deoxyguanosine phosphate; guanyl deoxyribonucleotide; purine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite
guanine [no description available]	2.99	4	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.25	1	0	guanosines; purines D-ribonucleoside	fundamental metabolite
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.92	4	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	1.99	1	0

Condition	Relationship Strength	Studies	Trials
Keratosis, Oral [description not available]	2.58	2	0
Cancer of the Tongue [description not available]	2.21	1	0
Leukoplakia, Oral A white patch seen on the oral mucosa. It is considered a premalignant condition and is often tobacco-induced. When evidence of Epstein-Barr virus is present, the condition is called hairy leukoplakia (LEUKOPLAKIA, HAIRY).	2.58	2	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.21	1	0
Hepatocellular Carcinoma [description not available]	2.46	2	0
Cancer of Liver [description not available]	2.96	4	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.46	2	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.96	4	0
Carcinoma, Epidermoid [description not available]	2.83	3	0
Cancer of Mouth [description not available]	3.35	6	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.83	3	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	3.35	6	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.15	1	0
Alcohol Abuse [description not available]	2.15	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.15	1	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	2.15	1	0
Cancer of Ovary [description not available]	2.52	2	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.52	2	0
Leukemia, Lymphoblastic, Acute, T Cell [description not available]	2.49	2	0
Benign Neoplasms [description not available]	4.36	4	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	4.36	4	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	3.92	12	0
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma A leukemia/lymphoma found predominately in children and young adults and characterized LYMPHADENOPATHY and THYMUS GLAND involvement. It most frequently presents as a lymphoma, but a leukemic progression in the bone marrow is common.	2.49	2	0
Cancer of Lung [description not available]	3.42	7	0
Lung Neoplasms Tumors or cancer of the LUNG.	3.42	7	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.44	2	0
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	2.13	1	0
T-Cell Lymphoma [description not available]	2.45	2	0
Delayed Effects, Prenatal Exposure [description not available]	2.74	3	0
Lymphoma, T-Cell A group of heterogeneous lymphoid tumors representing malignant transformations of T-lymphocytes.	2.45	2	0
Experimental Hepatoma [description not available]	3.66	3	0
Germinoblastoma [description not available]	2.44	2	0
Cancer of the Thymus [description not available]	2.44	2	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.44	2	0
Thymus Neoplasms Tumors or cancer of the THYMUS GLAND.	2.44	2	0
Experimental Neoplasms [description not available]	3.51	8	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3.41	7	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.11	5	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.42	2	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	3.46	1	1
Cancer of Skin [description not available]	3.87	12	0
Skin Neoplasms Tumors or cancer of the SKIN.	3.87	12	0
Aneuploid [description not available]	2.02	1	0
Chromosome-Defective Micronuclei [description not available]	2.02	1	0
Adenoma, Hepatocellular [description not available]	2	1	0
Breast Cancer [description not available]	3.51	8	0
Breast Neoplasms Tumors or cancer of the human BREAST.	3.51	8	0
Condition, Preneoplastic [description not available]	2.7	3	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.7	3	0
B-Cell Chronic Lymphocytic Leukemia [description not available]	2.03	1	0
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	2.03	1	0
Embryopathies [description not available]	2.03	1	0
Cancer of Stomach [description not available]	2.03	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.03	1	0
Multiple Primary Neoplasms [description not available]	2.04	1	0
Sarcoma, Epithelioid [description not available]	1.96	1	0
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	1.96	1	0
Soft Tissue Neoplasms Neoplasms of whatever cell type or origin, occurring in the extraskeletal connective tissue framework of the body including the organs of locomotion and their various component structures, such as nerves, blood vessels, lymphatics, etc.	1.96	1	0
Adenoma, Basal Cell [description not available]	2.39	2	0
Carcinoma, Anaplastic [description not available]	2.39	2	0
Papilloma, Squamous Cell [description not available]	2.38	2	0
Neoplasms, Sebaceous Gland [description not available]	1.98	1	0
Adenoma A benign epithelial tumor with a glandular organization.	2.39	2	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.39	2	0
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.38	2	0
Contact Dermatitis [description not available]	2.4	2	0
Anasarca [description not available]	1.99	1	0
Innate Inflammatory Response [description not available]	1.99	1	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	2.4	2	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	1.99	1	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	1.99	1	0
Experimental Mammary Neoplasms [description not available]	2.9	4	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2	1	0
Adenocarcinoma, Basal Cell [description not available]	1.97	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.97	1	0

dibenzo(a,l)pyrene

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Research Demand Index: 17.69

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