4,6-diamino-5-n-formamidopyrimidine profile

4,6-diamino-5-n-formamidopyrimidine (also known as 4,6-diamino-5-formamidopyrimidine or DAPFP) is a heterocyclic organic compound that is the building block of the DNA base adenine. It is synthesized through a series of chemical reactions that involve the condensation of formamide with guanidine. DAPFP is a key intermediate in the biosynthesis of adenine, which is an essential component of DNA and RNA. It plays a crucial role in cellular processes such as replication, transcription, and protein synthesis. DAPFP is also an important component of several drugs, including antiviral and anticancer agents. Researchers study DAPFP to understand the mechanisms of DNA synthesis and repair, as well as to develop new therapeutic agents targeting these processes. It is also of interest due to its potential role in the origin of life, as it is thought to have been one of the first organic molecules to form on early Earth.'

4,6-diamino-5-N-formamidopyrimidine: formed when adenine is exposed to ionizing radiation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4,6-diamino-5-formamidopyrimidine : A member of the class of aminopyrimidines that is 4,6-diaminopyrimidine bearing an additional formamido substituent at position 5. A DNA lesion formed when DNA exposed to ionising radiation. [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]

ID Source	ID
PubMed CID	114926
CHEBI ID	27983
SCHEMBL ID	435598
MeSH ID	M0118355

Synonym
fapy
4,6-diamino-5-n-formamidopyrimidine
C06502
4,6-diamino-5-formamidopyrimidine
5122-36-1
fapyade
FT-0693369
formamide, n-(4,6-diamino-5-pyrimidinyl)-
n-(4,6-diaminopyrimidin-5-yl)formamide
fapy-adenine
AKOS006271503
4,6-diamino-5-(formylamino)-pyrimidine
n-(4,6-diamino-5-pyrimidinyl)formamide
4,6-diamino-5-(formylamino)pyrimidine
SCHEMBL435598
4,6-diamino-5-pyrimidinylformamide
CHEBI:27983
4,6-diamino-5-pyrimidinylformamide #
MVYUVUOSXNYQLL-UHFFFAOYSA-N
DTXSID20199228
n-(4,6-diamino-5-pyrimidinyl)-formamide
HY-113303
Q27103440
CS-0059551
C15896
MS-22866
SB57660

Excerpt	Relevance	Reference
"A dose-response relationship between gamma-irradiation and the cleavage of the imidazole ring of adenine in DNA to form formamidopyrimidine has been demonstrated."	( A dose-response study on opening of imidazole ring of adenine in DNA by ionizing radiation. Chetsanga, CJ; Grigorian, C, 1983)	0.27
" Data from correlation analysis of the log ratios for normal tissues from cancer were consistent with an age-dependent, dose-response relationship."	( Age-related radical-induced DNA damage is linked to prostate cancer. Barker, EA; Johnson, PM; Malins, DC; Polissar, NL; Vinson, MA; Wheeler, TM, 2001)	0.31

Class	Description
aminopyrimidine	A member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives.
formamidopyrimidine
[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]

Pathway	Proteins	Compounds
DNA Repair	255	47
Base Excision Repair	35	23
Base-Excision Repair, AP Site Formation	17	16
Depyrimidination	15	9
Cleavage of the damaged pyrimidine	10	9

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (7.14)	18.7374
1990's	14 (33.33)	18.2507
2000's	14 (33.33)	29.6817
2010's	10 (23.81)	24.3611
2020's	1 (2.38)	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	2 (4.44%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	43 (95.56%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
adenine [no description available]	3.87	12	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cytosine [no description available]	2.68	3	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	1.98	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	2.41	2	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
thymine [no description available]	2.7	3	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
trimethylamine [no description available]	1.98	1	methylamines; tertiary amine	Escherichia coli metabolite; human xenobiotic metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	3.11	5	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
anthralin Anthralin: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.. anthralin : An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.	1.98	1	anthracenes	antipsoriatic
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	2.1	1	nitrogen mustard; organochlorine compound	alkylating agent
2-acetylaminofluorene 2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.	1.98	1	2-acetamidofluorenes	antimitotic; carcinogenic agent; epitope; mutagen
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.68	3	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.05	1	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.05	1	imidazolidine-2,4-dione
thymine glycol thymine glycol: forms photodimers (thymine dimers) under UV; RN given refers to cpd without isomeric designation	2.7	3	hydroxypyrimidine
sodium nitrate sodium nitrate : The inorganic nitrate salt of sodium.	1.98	1	inorganic nitrate salt; inorganic sodium salt	fertilizer; NMR chemical shift reference compound
osmium tetroxide Osmium Tetroxide: (T-4)-Osmium oxide (OsO4). A highly toxic and volatile oxide of osmium used in industry as an oxidizing agent. It is also used as a histological fixative and stain and as a synovectomy agent in arthritic joints. Its vapor can cause eye, skin, and lung damage.. osmium tetroxide : An osmium coordination entity consisting of four oxygen atoms bound to a central osmium atom via covalent double bonds.	2	1	osmium coordination entity	fixative; histological dye; oxidising agent; poison
isodialuric acid isodialuric acid: structure given in first source. 5,6-dihydroxyuracil : A nucleobase analogue that is uracil substituted at positions 5 and 6 by hydroxy groups.	2.44	2	hydroxypyrimidine; nucleobase analogue; pyrimidone	Mycoplasma genitalium metabolite
7-methyladenine 7-methyladenine: potential marker for monitoring exposure to methylatingcarcinogens. 7-methyladenine : Adenine substituted with a methyl group at position N-7.	2	1	methyladenine	metabolite
5-hydroxyuracil 5-hydroxyuracil: used in treatment of colonic adenocarcinoma	2.7	3	hydroxypyrimidine
isouramil isouramil: aglycone of convicine	2	1
pyrimidine dimers Pyrimidine Dimers: Dimers found in DNA chains damaged by ULTRAVIOLET RAYS. They consist of two adjacent PYRIMIDINE NUCLEOTIDES, usually THYMINE nucleotides, in which the pyrimidine residues are covalently joined by a cyclobutane ring. These dimers block DNA REPLICATION.	2.01	1
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.5	8	oxygen hydride; oxygen radical; reactive oxygen species
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.	2.07	1	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
fe(iii)-edta Fe(III)-EDTA: iron fortifying agent; RN given refers to parent cpd	1.97	1	iron coordination entity
glycosides [no description available]	2.08	1
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	2.01	1	diphosphate ion
5-hydroxycytosine [no description available]	2.4	2
8-hydroxyadenine 8-hydroxyadenine: xanthine oxidase reacted adenine metabolite in epidermis of hairless mice; structure. 8-oxoadenine : An oxopurine that is adenine bearing a single oxo substituent at position 8.. 8-hydroxyadenine : A nucleobase analogue that is adenine bearing a single hydroxy substituent at position 8.	3.61	9	6-aminopurines; heteroaryl hydroxy compound; nucleobase analogue; oxopurine	bacterial metabolite; human 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.	2.1	1
8-oxo-2'-deoxyadenosine 8-hydroxy-2'-deoxyadenosine: structure in first source	2.03	1	purine 2'-deoxyribonucleoside
8,5'-cyclo-2'-deoxyadenosine 8,5'-cyclo-2'-deoxyadenosine : An organic heterotetracyclic compound obtained by intramolecular formation of a C-C bond between positions 8 and 5' of 2'-deoxyadenosine.	2.45	2	aromatic amine; bridged compound; diol; N-glycosyl compound; organic heterotetracyclic compound	Mycoplasma genitalium metabolite
oligonucleotides [no description available]	3.01	4
guanidinohydantoin guanidinohydantoin: structure in first source. 5-guanidinohydantoin : An imidazolidine-2,4-dione substituted by a guanidino group at position 5.	2.05	1	guanidines; imidazolidine-2,4-dione
spiroiminodihydantoin spiroiminodihydantoin: structure in first source. spiroiminodihydantoin : An azaspiro compound that is 1,3,6,8-tetraazaspiro[4.4]non-6-ene which is substituted by oxo groups at positions 2, 4, and 9. Both enantiomers are highly mutagenic products resulting from the oxidation of guanine and 8-oxo-7,8-dihydroguanine in DNA by reactive oxygen species.	2.05	1	azaspiro compound	mutagen
orabase Orabase: used in therapy of oral mucosal ulcers	2.02	1
deoxyguanosine [no description available]	2.55	2	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanine [no description available]	5.12	14	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.	2.05	1	guanosines; purines D-ribonucleoside	fundamental metabolite
hypoxanthine [no description available]	2.68	3	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
7-methylguanine 7-methylguanine: RN given refers to unlabeled cpd; structure. 7-methylguanine : A methylguanine that is guanine substituted by a methyl group at position 7. It is a metabolite obtained during the methylation of DNA.. 2-imino-7-methyl-1,2,3,7-tetrahydro-6H-purin-6-one : A 7-methylguanine that is 1,2,3,7-tetrahydro-6H-purin-6-one substituted by an imino group at position 2 and a methyl group at position 7.. 2-amino-7-methyl-7H-purin-6-ol : A 7-methylguanine that is 7H-purine substituted by an amino group at position 2, a methyl group at position 7 and a hydroxy group at position 6.. 2-amino-7-methyl-1,7-dihydro-6H-purin-6-one : A 7-methylguanine that is 1,7-dihydro-6H-purin-6-one substituted by an amino group at position 2 and a methyl group at position 7.	2.39	2	7-methylguanine
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.68	3	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
8-hydroxyguanine 7,8-dihydro-8-oxoguanine: was substituted for guanine at G(8), G(9), G(14), or G(15) in the human telomeric oligonucleotide 5'-d[AGGGTTAG(8)G(9)GTT AG(14)G(15)GTTAGGGTGT]-3'. 7,8-dihydro-8-oxoguanine : An oxopurine that is guanine in which the hydrogen at position 8 is replaced by an oxo group and in which the nitrogens at positions 7 and 9 each bear a hydrogen.	4.98	12	oxopurine
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.25	1	guanosines	biomarker

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.13	1
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.	2.13	1
Benign Paroxysmal Peritonitis [description not available]	2.04	1
Familial Mediterranean Fever A group of HEREDITARY AUTOINFLAMMATION DISEASES, characterized by recurrent fever, abdominal pain, headache, rash, PLEURISY; and ARTHRITIS. ORCHITIS; benign MENINGITIS; and AMYLOIDOSIS may also occur. Homozygous or compound heterozygous mutations in marenostrin gene encoding PYRIN result in autosomal recessive transmission; simple heterozygous, autosomal dominant form of the disease also exists with mutations in the same gene.	2.04	1
Cancer of Liver [description not available]	2.68	3
Cancer of Lung [description not available]	2.41	2
Liver Neoplasms Tumors or cancer of the LIVER.	2.68	3
Lung Neoplasms Tumors or cancer of the LUNG.	2.41	2
Colorectal Cancer [description not available]	2.06	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.06	1
Cancer of Cervix [description not available]	2.43	2
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.43	2
Breast Cancer [description not available]	2.03	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.03	1
Cancer, Radiation-Induced [description not available]	2.9	1
Condition, Preneoplastic [description not available]	2.9	1
Cancer of Skin [description not available]	2.9	1
Kaposi Disease [description not available]	3.31	2
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.9	1
Skin Neoplasms Tumors or cancer of the SKIN.	2.9	1
Xeroderma Pigmentosum A rare, pigmentary, and atrophic autosomal recessive disease. It is manifested as an extreme photosensitivity to ULTRAVIOLET RAYS as the result of a deficiency in the enzyme that permits excisional repair of ultraviolet-damaged DNA.	3.31	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	1.98	1
Experimental Hepatoma [description not available]	1.98	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	1.98	1
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	1
Cancer of Prostate [description not available]	2	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2	1
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).	1.97	1

4,6-diamino-5-n-formamidopyrimidine

Description

Cross-References

Synonyms (27)

Research Excerpts

Dosage Studied

Drug Classes (2)

Pathways (5)

Research

Studies (42)

Market Indicators

Research Demand Index: 11.19

Study Types