cyclopenta(c,d)pyrene profile

Cyclopenta(c,d)pyrene is a polycyclic aromatic hydrocarbon (PAH) that has been identified as a potent mutagen and carcinogen. Its synthesis often involves complex organic chemistry reactions, using starting materials like naphthalene derivatives. The compound is commonly found in environmental samples, particularly in coal tar, diesel exhaust, and cigarette smoke. Due to its carcinogenic properties, cyclopenta(c,d)pyrene is extensively studied to understand its molecular mechanisms of action, particularly its ability to interact with DNA and trigger cellular mutations. Research also focuses on developing strategies for its removal from environmental samples and minimizing human exposure.'

cyclopenta(c,d)pyrene: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	33743
CHEMBL ID	350278
CHEBI ID	82279
MeSH ID	M0066265

Synonym
27208-37-3
cyclopenta[cd]pyrene
acepyrene
cyclopenta(cd)pyrene
acepyrylene
brn 2047004
cyclopenta(c,d)pyrene
cyclopenteno(c,d)pyrene
ccris 6930
chebi:82279 ,
CHEMBL350278
C19173
29xd62tn4d ,
unii-29xd62tn4d
FT-0638680
cyclopenta(cd)pyrnene
cyclopenta(cd)pyrene [iarc]
BZCXQYVNASLLQO-UHFFFAOYSA-N
DTXSID7074822
cyclopenta[cd]pyrene; acepyrene; acepyrylene; cyclopenta[c,d]pyrene
cyclopenta[c,d]pyrene 10 microg/ml in cyclohexane
cyclopenta[c,d]pyrene 10 microg/ml in acetonitrile
J-016691
Q27155853
pentacyclo[12.3.1.04,17.07,16.010,15]octadeca-1(18),2,4(17),5,7(16),8,10(15),11,13-nonaene
pentacyclo[12.3.1.0?,??.0?,??.0??,??]octadeca-1(18),2,4(17),5,7(16),8,10(15),11,13-nonaene

Excerpt	Relevance	Reference
" Antimutagenicity is investigated through the analysis of respondents in dose-response assays, when two different molecules are administered separately and as a mixture to a respondent system."	( The analysis of the joint effect of substances on reversion systems and the assessment of antimutagenicity. Ambrosino, P; Barale, R; Barrai, I; Beretta, M; Loprieno, N; Micheletti, R; Sbrana, C; Scapoli, C, 1992)	0.28
"55 mumol) with the dose-response relationship indicating a saturation of tumor multiplicity at approximately 7 tumors/animal."	( Dose-response relationships of the tumorigenicity of cyclopenta[cd]pyrene, benzo[a]pyrene and 6-nitrochrysene in a newborn mouse lung adenoma bioassay. Busby, WF; Cornelisse, J; Kellenbach, ER; Lugtenburg, J; Stevens, EK, 1988)	0.27
" This reverse dose-response may be due to the relatively high cytotoxicity of CPEP, BP, which was compared to CPEP at the low dose, elicited tumors in 100% of the mice."	( Carcinogenicity of the environmental pollutants cyclopenteno-[cd]pyrene and cyclopentano[cd]pyrene in mouse skin. Cavalieri, E; Munhall, A; Rogan, E; Toth, B, 1981)	0.26

Class	Description
pyrenes
[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]

Assay ID	Title	Year	Journal	Article
AID160321	Competition for [3H]benzo[a]pyrene-binding site of polycyclic aromatic hydrocarbon binding protein (PBP) from mouse liver	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Voronoi binding site model of a polycyclic aromatic hydrocarbon binding protein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	12 (42.86)	18.7374
1990's	7 (25.00)	18.2507
2000's	6 (21.43)	29.6817
2010's	3 (10.71)	24.3611
2020's	0 (0.00)	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	0 (0.00%)	5.53%
Reviews	1 (3.33%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	29 (96.67%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid 3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid: structure given in first source; NMDA receptor antagonist	2.05	1
2-aminofluorene [no description available]	1.97	1
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.	2.66	3	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.	3.47	8	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	1.96	1	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	1.96	1	ortho-fused polycyclic arene; tetraphenes
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.11	1	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	1.97	1	naphthylamine	human xenobiotic metabolite
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	3.08	1	ortho- and peri-fused polycyclic arene; perylenes
benzo(j)fluoranthene benzo(j)fluoranthene: dihydrodiol metabolites identified as mutagens; structure given in first source	2.11	1	naphthalenes
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	1.97	1	ortho- and peri-fused polycyclic arene
benzo(k)fluoranthene [no description available]	2.03	1	naphthalenes
acenaphthylene acenaphthylene: RN given refers to parent cpd. acenaphthylene : A ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar.	2.44	2	acenaphthylenes; ortho- and peri-fused polycyclic arene; ortho- and peri-fused tricyclic hydrocarbon
benzotriphenylene [no description available]	1.97	1	carbopolycyclic compound
chrysene chrysene: structure in Merck Index, 9th ed, #2252. chrysene : An ortho-fused polycyclic arene found commonly in the coal tar.	1.97	1	ortho-fused polycyclic arene	plant metabolite
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	3.21	6	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
allylisopropylacetamide Allylisopropylacetamide: An allylic compound that acts as a suicide inactivator of CYTOCHROME P450 by covalently binding to its heme moiety or surrounding protein.	1.96	1
1-aminoanthracene [no description available]	1.97	1	anthracenamine
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.08	1	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
9-aminophenanthrene [no description available]	1.97	1	phenanthrenamine
trichloroepoxypropane Trichloroepoxypropane: A potent epoxide hydrase and aryl hydrocarbon hydroxylase inhibitor. It enhances the tumor-initiating ability of certain carcinogens.	1.97	1
6-nitrochrysene 6-nitrochrysene: RN given refers to cpd with locant for nitro group in position 6	1.97	1	carbopolycyclic compound
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.	1.96	1	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
9-hydroxybenzo(a)pyrene 9-hydroxybenzo(a)pyrene: RN given refers to unlabeled parent cpd	1.97	1	ortho- and peri-fused polycyclic arene
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.03	1	benzenes; phenyl acetates
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.39	2	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
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.	1.96	1	epoxide	intercalator
benz(j)aceanthrylene [no description available]	1.98	1	phenanthrenes
aceanthrylene aceanthrylene: structure given in first source	2	1	ortho- and peri-fused polycyclic arene
propylisopropylacetamide propylisopropylacetamide: structure	1.96	1
2-ethynylnaphthalene 2-ethynylnaphthalene: RN given refers to unlabeled parent cpd	2	1
1-ethynylpyrene 1-ethynylpyrene: RN & structure given in first source; RN not in Chemline 12/84	2	1
9-ethynylphenanthrene 9-ethynylphenanthrene: structure given in first source	2	1
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	1.96	1	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	2.36	2	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid: RN given refers to cpd without isomeric designation; (S-(E,Z,Z,Z))-isomer caused dose-dependent constriction of cat coronary arteries; structure in first source. 15-HPETE : A HPETE that consists of (5Z,8Z,11Z,13E)-icosatetraenoic acid in which the hydroperoxy group is located at position 15.	1.97	1	HPETE	human xenobiotic metabolite
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	2.03	1
oligonucleotides [no description available]	2.45	2
cyclopenta(cd)pyrene 3,4-oxide cyclopenta(cd)pyrene 3,4-oxide: structure given in first source	2.36	2
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.03	1	guanosines; purines D-ribonucleoside	fundamental metabolite
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.	2.39	2

Condition	Relationship Strength	Studies
Experimental Neoplasms [description not available]	2.87	4
Cancer of Skin [description not available]	3.22	6
Skin Neoplasms Tumors or cancer of the SKIN.	3.22	6
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.	2.36	2
Papilloma, Squamous Cell [description not available]	1.98	1
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)	1.98	1
Adenoma, Basal Cell [description not available]	1.97	1
Cancer of Lung [description not available]	1.97	1
Adenoma A benign epithelial tumor with a glandular organization.	1.97	1
Lung Neoplasms Tumors or cancer of the LUNG.	1.97	1

cyclopenta(c,d)pyrene

Description

Cross-References

Synonyms (26)

Research Excerpts

Dosage Studied

Drug Classes (1)

Bioassays (1)

Research

Studies (28)

Market Indicators

Research Demand Index: 22.40

Study Types