Page last updated: 2024-10-24

adenosine catabolic process

Definition

Target type: biologicalprocess

The chemical reactions and pathways resulting in the breakdown of adenosine, adenine riboside, a ribonucleoside found widely distributed in cells of every type as the free nucleoside and in combination in nucleic acids and various nucleoside coenzymes. [GOC:go_curators]

Adenosine catabolism is a fundamental metabolic pathway that involves the breakdown of adenosine into its constituent components: adenine and ribose. This process occurs primarily in the cytoplasm of cells, and it is catalyzed by a series of enzymes.

The first step in adenosine catabolism is the deamination of adenosine by adenosine deaminase (ADA) to form inosine. ADA is a key regulatory enzyme in this pathway, and its deficiency is associated with severe immunodeficiency.

Inosine is then further metabolized by purine nucleoside phosphorylase (PNP) to form hypoxanthine. Hypoxanthine can then be converted to xanthine by xanthine oxidase, and finally to uric acid, the end product of purine metabolism.

Adenosine catabolism is tightly regulated, ensuring the appropriate balance of purine nucleotide levels within the cell. It plays a crucial role in maintaining cellular energy homeostasis, regulating cell growth and differentiation, and influencing immune function.

Additionally, adenosine catabolism is closely linked to other important metabolic pathways, such as the salvage pathway for purine nucleotides and the synthesis of NAD+.

Disruptions in adenosine catabolism can lead to a variety of pathological conditions, including immunodeficiency, gout, and Lesch-Nyhan syndrome. Therefore, understanding the intricacies of this pathway is essential for developing novel therapeutic strategies for these diseases.'
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Proteins (5)

ProteinDefinitionTaxonomy
Adenosine deaminase An adenosine deaminase that is encoded in the genome of cow. [OMA:P56658, PRO:DNx]Bos taurus (cattle)
Adenosine deaminase-like proteinAn adenosine deaminase-like protein that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q6DHV7]Homo sapiens (human)
Xanthine dehydrogenase/oxidaseA xanthine dehydrogenase/oxidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P47989]Homo sapiens (human)
Adenosine deaminaseAn adenosine deaminase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P00813]Homo sapiens (human)
Adenosine deaminaseAn adenosine deaminase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P00813]Homo sapiens (human)

Compounds (113)

CompoundDefinitionClassesRoles
adenine6-aminopurines;
purine nucleobase
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
taxifolin3'-hydroxyflavanones;
4'-hydroxyflavanones;
dihydroflavonols;
pentahydroxyflavanone;
secondary alpha-hydroxy ketone
5,6-dimethylbenzimidazole5,6-dimethylbenzimidazole : A dimethylbenzimidazole carrying methyl substituents at positions 5 and 6.

5,6-dimethylbenzimidazole: RN given refers to parent cpd
dimethylbenzimidazoleEscherichia coli metabolite;
human metabolite
niacinNiacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.

nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.

vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).
pyridine alkaloid;
pyridinemonocarboxylic acid;
vitamin B3
antidote;
antilipemic drug;
EC 3.5.1.19 (nicotinamidase) inhibitor;
Escherichia coli metabolite;
human urinary metabolite;
metabolite;
mouse metabolite;
plant metabolite;
vasodilator agent
9-(2-hydroxy-3-nonyl)adenine9-(2-hydroxy-3-nonyl)adenine: specific inhibitor of adenosine deaminase
propyl gallatePropyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.trihydroxybenzoic acid
adenosine monophosphateAdenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate
adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
methyl gallatemethyl 3,4,5-trihydroxybenzoate : A gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties.

methyl gallate: has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum
gallate esteranti-inflammatory agent;
antioxidant;
plant metabolite
methylparabenmethylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.

methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd
parabenantifungal agent;
antimicrobial food preservative;
neuroprotective agent;
plant metabolite
benzilbenzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.

benzil: structure
alpha-diketone;
aromatic ketone
2-chloroadenosine5-chloroformycin A: structure given in first sourcepurine nucleoside
2-fluoroadenosineadenosines;
organofluorine compound
catechin(+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.

catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.

Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.

rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin
catechinantioxidant;
plant metabolite
2-aminopurine2-aminopurine : The parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position.

2-Aminopurine: A purine that is an isomer of ADENINE (6-aminopurine).

aminopurine : Any purine having at least one amino substituent.
2-aminopurines;
nucleobase analogue
antimetabolite
3-hydroxyflavone3-hydroxyflavone: structure given in first source

flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.
flavonols;
monohydroxyflavone
5-methylbenzimidazole5-methyl-1H-benzimidazole : A member of the class of imidazoles that is 1H-benzimidazole in which the hydrogen at position 5 is substituted by a methyl group.

5-methylbenzimidazole: structure in first source
imidazoles
isovanillinisovanillin : A member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase.

isovanillin: inhibits aldehyde oxidase
benzaldehydes;
monomethoxybenzene;
phenols
animal metabolite;
antidiarrhoeal drug;
antifungal agent;
EC 1.2.3.1 (aldehyde oxidase) inhibitor;
HIV protease inhibitor;
plant metabolite
3-hydroxy-1-benzopyran-2-one3-hydroxycoumarin: Photoprotective from sea urchin gametes and embryonic cells; structure in first source

hydroxycoumarin : Any coumarin carrying at least one hydroxy substituent.
hydroxycoumarin
2'-deoxyadenosine2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first sourcepurine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
dideoxyadenosineDideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.adenosines;
purine 2',3'-dideoxyribonucleoside
EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) inhibitor
vidarabineadenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.beta-D-arabinoside;
purine nucleoside
antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
3-deazaadenosine3-deazaadenosine: RN given refers to parent cpd.
butylated hydroxyanisole
coformycincoformycinsEC 3.5.4.4 (adenosine deaminase) inhibitor
2,6-diaminopurine9H-purine-2,6-diamine : A member of the class of 2,6-diaminopurines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by amino groups.2,6-diaminopurines;
primary amino compound
antineoplastic agent
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acidchromanol;
monocarboxylic acid;
phenols
antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
adefoviradefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.

adefovir: inhibitor of African swine fever virus

adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).
6-aminopurines;
ether;
phosphonic acids
antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
adenosinequinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlitadenosines;
purines D-ribonucleoside
analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
2'3'-didehydro-2'3'-dideoxyadenosine2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source
o-(6)-methylguanine6-O-methylguanine : A methylguanine in which the methyl group is positioned on the oxygen at position 6. Formed in DNA by alkylation of the oxygen atom of guanine, most often by N-nitroso compounds and sometimes due to methylation by other compounds such as endogenous S-adenosylmethionine, it base-pairs to thymine rather than cytidine, causing a G:C to A:T transition in DNA.

methylguanine : A 2-aminopurine that is guanine bearing a single methyl substituent.

O-(6)-methylguanine: structure
methylguaninemutagen
secoisolariciresinol(-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.

secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups

secoisolariciresinol: RN given refers to ((R-(R*,R*))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source
secoisolariciresinolantidepressant;
phytoestrogen;
plant metabolite
tangeretinpentamethoxyflavone : A methoxyflavone that is flavone substituted by a five methoxy groups.

tangeretin : A pentamethoxyflavone flavone with methoxy groups at positions 4', 5, 6 , 7 and 8.

tangeretin: structure given in first source; from citrus plants; inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro
pentamethoxyflavoneantineoplastic agent;
plant metabolite
nebularinenebularine : A purine ribonucleoside that is 9H-purine attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage.

nebularine: structure
purine ribonucleoside;
purines D-ribonucleoside
fungal metabolite
isoscopoletinisoscopoletin : A hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone.aromatic ether;
hydroxycoumarin
plant metabolite
2-hydroxychavicol2-hydroxychavicol: antimutagen from betel leaf; structure given in first source
2-aminoadenosinepurine nucleoside
epicatechin(-)-epicatechin : A catechin with (2R,3R)-configuration.catechin;
polyphenol
antioxidant
gallocatechol(-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.catechin;
flavan-3,3',4',5,5',7-hexol
antioxidant;
food component;
plant metabolite
nobiletinnobiletin : A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.methoxyflavoneantineoplastic agent;
plant metabolite
4-aminopyrazolo(3,4-d)pyrimidine4-aminopyrazolo(3,4-d)pyrimidine: adenine analog which suppresses growth of E coli & Bacillus cereus; inhibits cell growth & purine biosynthesis in rat hepatoma
1-methylxanthine1-methyl-7H-xanthine : A 1-methylxanthine tautomer where the imidazole proton is located at the 7-position.

1-methylxanthine : A monomethylxanthine having the methyl group located at the 1-position. It is a metabolite of caffeine in humans.

1-methylxanthine: urinary metabolite of caffeine
1-methylxanthinemouse metabolite
monocerinmonocerin: structure in first sourcehydroxybenzoic acidmetabolite
2,6-diamino-9-(2-hydroxyethoxymethyl)purine2,6-diamino-9-(2-hydroxyethoxymethyl)purine: adenosine deaminase converts above cpd to acylovir
8-azaadenosineN-glycosyl compound
8-aminoadenosine
6-methoxypurine arabinoside
o(6)-methyldeoxyguanylic acidO(6)-methyldeoxyguanylic acid: incorporated into DNA by DNA polymerase I & II
febuxostatfebuxostat : A 1,3-thiazolemonocarboxylic acid that is 4-methyl-1,3-thiazole-5-carboxylic acid which is substituted by a 3-cyano-4-(2-methylpropoxy)phenyl group at position 2. It is an orally-active, potent, and selective xanthine oxidase inhibitor used for the treatment of chronic hyperuricaemia in patients with gout.

Febuxostat: A thiazole derivative and inhibitor of XANTHINE OXIDASE that is used for the treatment of HYPERURICEMIA in patients with chronic GOUT.
1,3-thiazolemonocarboxylic acid;
aromatic ether;
nitrile
EC 1.17.3.2 (xanthine oxidase) inhibitor
9-(2-hydroxy-3-nonyl)adenine(2R,3S)-EHNA : EHNA of absolute configuration 2R,3S. Selective inhibitor of cGMP-stimulated phosphodiesterase (PDE2) (IC50 = 0.8 - 4 mM). Also a potent inhibitor of adenosine deaminase.EHNAEC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
EC 3.5.4.4 (adenosine deaminase) inhibitor
9-(2-hydroxy-3-nonyl)adenine(2S,3R)-EHNA : EHNA of absolute configuration 2S,3R.EHNA
cirsimarincirsimarin: a flavone glycoside from Microtea debilis; structure given in first sourceflavonoids;
glycoside
1-deazaadenosine1-deazaadenosine: inhibits nucleic acid & protein synthesis; structure given in first source
4'-hydroxyflavanone4'-hydroxyflavanone: structure in first source

4'-hydroxyflavanones : Any hydroxyflavanone having a hydroxy substituent located at position 4'.
4'-hydroxyflavanones;
monohydroxyflavanone
rubrofusarin Brubrofusarin B : A benzochromenone that is rubrofusarin in which the hydroxy group at position 6 has been converted to the corresponding methyl ether.aromatic ether;
benzochromenone;
naphtho-gamma-pyrone;
phenols;
polyketide
Aspergillus metabolite
yemuoside ym(10)yemuoside YM(10): from Stauntonia chinensis Decne; structure given in first source
methyl 3,4-dihydroxybenzoatecatechols;
methyl ester
antioxidant;
neuroprotective agent;
plant metabolite
naringenin(S)-naringenin : The (S)-enantiomer of naringenin.(2S)-flavan-4-one;
naringenin
expectorant;
plant metabolite
pentostatinpentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia.

Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.
coformycinsantimetabolite;
antineoplastic agent;
Aspergillus metabolite;
bacterial metabolite;
EC 3.5.4.4 (adenosine deaminase) inhibitor
formycinformycinantineoplastic agent
y-700
1-deaza-2-chloro-n(6)-cyclopentyladenosine1-deaza-2-chloro-N(6)-cyclopentyladenosine: adenosine A(1) receptor agonist
fludarabinepurine nucleoside
thioguanine anhydrousThioguanine: 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-aminopurinesanticoronaviral agent;
antimetabolite;
antineoplastic agent
merbaronemerbarone: structure given in first source
quercetin7-hydroxyflavonol;
pentahydroxyflavone
antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
apigeninChamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.trihydroxyflavoneantineoplastic agent;
metabolite
luteolin3'-hydroxyflavonoid;
tetrahydroxyflavone
angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
quercitrinalpha-L-rhamnoside;
monosaccharide derivative;
quercetin O-glycoside;
tetrahydroxyflavone
antileishmanial agent;
antioxidant;
EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
plant metabolite
coniferaldehydeconiferaldehyde: from aqueous extract of Senra incana

coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.
cinnamaldehydes;
guaiacols;
phenylpropanoid
antifungal agent;
plant metabolite
daphnetinhydroxycoumarin
quercetin 3-o-glucopyranosidequercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells

quercetin 3-O-glucopyranoside: structure in first source
beta-D-glucoside;
monosaccharide derivative;
quercetin O-glucoside;
tetrahydroxyflavone
antineoplastic agent;
antioxidant;
antipruritic drug;
bone density conservation agent;
geroprotector;
histamine antagonist;
osteogenesis regulator;
plant metabolite
rutinHydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone
antioxidant;
metabolite
kaempferol7-hydroxyflavonol;
flavonols;
tetrahydroxyflavone
antibacterial agent;
geroprotector;
human blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
plant metabolite
genistein7-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
esculetinesculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.

esculetin: used in filters for absorption of ultraviolet light; structure
hydroxycoumarinantioxidant;
plant metabolite;
ultraviolet filter
7-hydroxycoumarin7-oxycoumarin: derivatives have anti-oxidant properties

umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.
hydroxycoumarinfluorescent probe;
food component;
plant metabolite
axillarinaxillarin : A dimethoxyflavone that is the 3,6-dimethyl ether derivative of quercetagetin.

axillarin: isolated from Pulicaria crispa or Filifdium sibiricum; structure given in first source
dimethoxyflavone;
tetrahydroxyflavone
plant metabolite
baicaleintrihydroxyflavoneangiogenesis inhibitor;
anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 4.1.1.17 (ornithine decarboxylase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hormone antagonist;
plant metabolite;
prostaglandin antagonist;
radical scavenger
chrysinchrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.7-hydroxyflavonol;
dihydroxyflavone
anti-inflammatory agent;
antineoplastic agent;
antioxidant;
EC 2.7.11.18 (myosin-light-chain kinase) inhibitor;
hepatoprotective agent;
plant metabolite
fisetin3'-hydroxyflavonoid;
7-hydroxyflavonol;
tetrahydroxyflavone
anti-inflammatory agent;
antioxidant;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
metabolite;
plant metabolite
galangin5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source

galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.
7-hydroxyflavonol;
trihydroxyflavone
antimicrobial agent;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
plant metabolite
3-methylquercetinisorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.7-hydroxyflavonol;
monomethoxyflavone;
tetrahydroxyflavone
anticoagulant;
EC 1.14.18.1 (tyrosinase) inhibitor;
metabolite
morinmorin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.

morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria)
7-hydroxyflavonol;
pentahydroxyflavone
angiogenesis modulating agent;
anti-inflammatory agent;
antibacterial agent;
antihypertensive agent;
antineoplastic agent;
antioxidant;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
hepatoprotective agent;
metabolite;
neuroprotective agent
myricetin7-hydroxyflavonol;
hexahydroxyflavone
antineoplastic agent;
antioxidant;
cyclooxygenase 1 inhibitor;
food component;
geroprotector;
hypoglycemic agent;
plant metabolite
santinsantin : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 3, 6 and 4' and hydroxy groups at positions 5 and 7 respectively.

santin: from Tanacetum microphyllum; structure given in first source
dihydroxyflavone;
trimethoxyflavone
plant metabolite
daidzein7-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
phytoestrogen;
plant metabolite
7-hydroxyflavone7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.hydroxyflavonoid
veronicastrosideluteolin 7-O-neohesperidoside : A disaccharide derivative that is luteolin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.

veronicastroside: a flavonoid; second source Yak. Zas. shows same melting point, absorption, Rf and color tests for lonicerin (luteolin-7-rhamnoglucoside from Lonicera) and veronicastroside (luteolin-7-neohesperidoside from Trachelospermum);
disaccharide derivative;
glycosyloxyflavone;
neohesperidoside;
trihydroxyflavone
antibacterial agent;
metabolite
3',4',7-trihydroxyisoflavone3',4',7-trihydroxyisoflavone : A 7-hydroxyisoflavone that is daidzein substituted by a hydroxy group at position 3'.

3',4',7-trihydroxyisoflavone: from Streptomyces sp OH-1049; structure given in first source
7-hydroxyisoflavonesantineoplastic agent;
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor;
metabolite
6,7,4'-trihydroxyisoflavone4',6,7-trihydroxyisoflavone : A hydroxyisoflavone that is daidzein bearing an additional hydroxy substituent at position 6.

6,7,4'-trihydroxyisoflavone: structure in first source
7-hydroxyisoflavonesanti-inflammatory agent;
antimutagen;
EC 1.14.18.1 (tyrosinase) inhibitor;
metabolite;
PPARalpha agonist;
PPARgamma agonist
topiroxostatFYX-051: xanthine oxidoreductase inhibitor
cycloolivilcycloolivil: a free radical scavenger with platelet aggregation inhibitory activity; isolated from the olive treelignan
glyciteinglycitein : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.7-hydroxyisoflavone;
methoxyisoflavone
fungal metabolite;
phytoestrogen;
plant metabolite
hypolaetin-8-glucosidehypolaetin-8-glucoside: isolated from Sideritis mugronensis; structure given in first source
kaempferol-3-o-rutinosidekaempferol-3-O-rutinoside: isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography; structure in first source

kaempferol-3-rutinoside : A kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme.
disaccharide derivative;
kaempferol O-glucoside;
rutinoside;
trihydroxyflavone
metabolite;
plant metabolite;
radical scavenger
4-methylesculetin4-methylesculetin: has antiinflammatory activity

6,7-dihydroxy-4-methylcoumarin : A hydroxycoumarin that is 4-methylcuomarin which is substituted by hydroxy groups at positions 3 and 4. A hyaluronan synthesis inhibitor. It has also been used as a fluorescent sensor to monitor the consumption of a boronic acid in Suzuki coupling reactions; fluorescence is readily detectable by the naked eye using a standard 365 nm UV lamp.
hydroxycoumarinanti-inflammatory agent;
antioxidant;
hyaluronan synthesis inhibitor
ombuineombuin : A dimethoxyflavone that is quercetin in which the hydroxy groups at positions 7 and 4' are replaced by methoxy groups. Isolated from Cyperus teneriffae, it exhibits anti-inflammatory activity.

ombuine: from rhizome of Alpinia tonkinensis
dimethoxyflavone;
flavonols;
trihydroxyflavone
anti-inflammatory agent;
plant metabolite
tilirosidetiliroside: isolated from seeds of Eremocarpus setigeruscinnamate ester;
glycosyloxyflavone;
monosaccharide derivative;
trihydroxyflavone
plant metabolite
2-amino-6-chloropurine6-chloroguanine : An organochlorine compound that is 7H-purin-2-amine substituted by a chloro group at position 6.

6-chloroguanine: an antimalarial that inhibits hypoxanthine-guanine-xanthine phosphoribosyltransferase; structure in first source
2-aminopurines;
organochlorine compound
4',7,8-trihydroxyisoflavone4',7,8-trihydroxyisoflavone: from Streptomyces sp OH-1049; structure given in first sourceisoflavones
broussochalcone abroussochalcone A: RN given for (E)-isomer; inhibits neutrophil respiratory burst; structure in first source
8-azanebularine8-azanebularine: structure in first source
fonsecinone afonsecinone A : A dimeric naphthopyran with formula C32H26O10, originally isolated from Aspergillus niger.

fonsecinone A: isolated from Aspergillus aculeatus; structure in first source
aromatic ether;
aromatic ketone;
biaryl;
cyclic ketone;
naphtho-gamma-pyrone;
polyphenol
antibacterial agent;
Aspergillus metabolite
salvianolic acid csalvianolic acid C: mTOR inhibitor from Salvia miltiorrhizabenzofurans
msh, 4-nle-7-phe-alpha-polypeptidedermatologic drug
4-hydroxycoumarin2-hydroxychromone: structurehydroxycoumarin
deoxyinosinepurine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
inosineinosines;
purines D-ribonucleoside
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
oxypurinolalloxanthine : A pyrazolopyrimidine that is 4,5,6,7-tetrahydro-H-pyrazolo[3,4-d]pyrimidine substituted by oxo groups at positions 4 and 6.

Oxypurinol: A xanthine oxidase inhibitor.
pyrazolopyrimidinedrug metabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor
allopurinolallopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.

Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.
nucleobase analogue;
organic heterobicyclic compound
antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
bropiriminepyrimidines
9-phenylguanine
adenalleneadenallene: structure given in first source; inhibits replication and cytopathic effects of HIV in vitro