Exact Mass: 274.0013

KEIO_ID G066

6-phospho-2-dehydro-D-gluconate

6-Phospho-2-dehydro-D-gluconate; 2-Dehydro-D-gluconate 6-phosphate

A ketoaldonic acid phosphate that is the 6-phospho derivative of 2-dehydro-D-gluconic acid.

L-Iduronate 2-sulfate

4-Ketocyclophosphamide

2-[bis(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione

4-Ketocyclophosphamide is a metabolite of cyclophosphamide. Cyclophosphamide (trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia) D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D010752 - Phosphoramide Mustards

3-Dehydro-L-gulonate 6-phosphate

2,4,5-Trihydroxy-3-oxo-6-phosphonooxyhexanoic acid

3-Dehydro-L-gulonate 6-phosphate is an intermediate in the metabolic pathways of glucose metabolism. Its chemical structure is characterized by a hexose sugar backbone with specific modifications. The "3-Dehydro" part of its name indicates the presence of a double bond at the third carbon atom due to the removal of two hydrogen atoms, which differentiates it from the corresponding sugar. The "L-gulonate" portion refers to its derivation from L-gulonic acid, a sugar acid. The "6-phosphate" indicates the presence of a phosphate group attached to the sixth carbon atom of the sugar. Biologically, 3-Dehydro-L-gulonate 6-phosphate plays a role in the metabolism of glucose. It is involved in the process of gluconeogenesis, which is the synthesis of glucose from non-carbohydrate sources, such as amino acids and glycerol. This pathway is particularly important during periods of fasting or low carbohydrate intake, where the body needs to maintain blood glucose levels for energy production. Additionally, 3-Dehydro-L-gulonate 6-phosphate may also be involved in other metabolic pathways, including the pentose phosphate pathway, which is important for the production of NADPH (an important reducing agent in the cell) and ribose-5-phosphate (a precursor for nucleotide synthesis). In summary, 3-Dehydro-L-gulonate 6-phosphate is a chemically modified sugar phosphate that serves as an intermediate in various metabolic pathways, particularly in the synthesis and breakdown of glucose. Its presence and regulation are crucial for maintaining energy balance and providing necessary building blocks for cellular processes in living organisms.

4-Ketoifosfamide

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinane-2,4-dione

4-Ketoifosfamide is a metabolite of ifosfamide. Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. It is sometimes abbreviated IFO. (Wikipedia) D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D010752 - Phosphoramide Mustards

D-Glucuronic acid 1-phosphate

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid

D-Glucuronic acid 1-phosphate is an end product of the UDP-glucuronic acid pathway. Formation of free glucuronic acid from UDP-glucuronic acid can be considered as the first step in the synthesis of vitamin C, a pathway that occurs in most vertebrates, although not in guinea pigs and primates, including humans. Free glucuronic acid can also be converted to pentose phosphate intermediates via the pentose pathway. The latter is interrupted in subjects with pentosuria, who have a deficiency in l-xylulose reductase (EC 1.1.1.10, an enzyme that belongs to the short-chain dehydrogenase/reductase family) and excrete abnormal amounts of l-xylulose. Some xenobiotics stimulate the formation of vitamin C in animals and enhance the excretion of l-xylulose in humans with pentosuria and have shown that aminopyrine, metyrapone and other xenobiotics cause an almost instantaneous increase in the conversion of UDP-glucuronic acid to glucuronic acid. It is usually stated that glucuronic acid formation from UDP-glucuronic acid is the result of two successive reactions comprising the hydrolysis of UDP-glucuronic acid to glucuronic acid 1-phosphate and UMP by nucleotide pyrophosphatase (E-NPP3, EC 3.6.1.9), followed by dephosphorylation of glucuronic acid 1-phosphate. Glucuronidation is responsible for conjugating potentially toxic lipophilic compounds with glucuronic acid, thereby producing molecules with greater aqueous solubility that is excreted more readily into urine and bile. The rate at which any compound may be glucuronidated depends on the concentration and activity of the UDP-glucuronosyltransferases as well as the concentration of the cofactor UDP-glucuronic acid. UDP-glucuronic acid is formed after oxidation of UDP-glucose by UDP-glucose dehydrogenase (UGDH, EC 1.1.1.22) with NAD as the electron acceptor. UDP-glucuronic acid may then be either used as the glucuronic acid donor for xenobiotic conjugation reactions by UDPglucuronosyltransferases (GlcAT-P, EC 2.4.1.17), or degraded to D-glucuronic acid 1-phosphate after the phosphodiester bond is cleaved by E-NPP3. E-NPP3 is the same enzyme that further reduces D-Glucuronic acid 1-phosphate to free D-glucuronic acid. Decreases in UDP-glucuronic acid concentration may be due to reduced availability of UDP-glucose or decreased UGDH activity or to increased activities of GlcAT-P or E-NPP3. Exposure to volatile anesthetics reduces hepatic UDP-glucuronic acid concentrations, and alters the rate of conjugation of compounds such as acetaminophen, bilirubin, diethylstilbestrol, iopanoic acid and valproic acid in a non-sex-dependent fashion in experimental mice. The depletion of UDP-glucuronic acid by anesthetics is caused by altered activity of microsomal E-NPP3. (PMID: 2167093, 16689937, 1276) [HMDB] D-Glucuronic acid 1-phosphate is an end product of the UDP-glucuronic acid pathway. Formation of free glucuronic acid from UDP-glucuronic acid can be considered as the first step in the synthesis of vitamin C, a pathway that occurs in most vertebrates, although not in guinea pigs and primates, including humans. Free glucuronic acid can also be converted to pentose phosphate intermediates via the pentose pathway. The latter is interrupted in subjects with pentosuria, who have a deficiency in l-xylulose reductase (EC 1.1.1.10, an enzyme that belongs to the short-chain dehydrogenase/reductase family) and excrete abnormal amounts of l-xylulose. Some xenobiotics stimulate the formation of vitamin C in animals and enhance the excretion of l-xylulose in humans with pentosuria and have shown that aminopyrine, metyrapone and other xenobiotics cause an almost instantaneous increase in the conversion of UDP-glucuronic acid to glucuronic acid. It is usually stated that glucuronic acid formation from UDP-glucuronic acid is the result of two successive reactions comprising the hydrolysis of UDP-glucuronic acid to glucuronic acid 1-phosphate and UMP by nucleotide pyrophosphatase (E-NPP3, EC 3.6.1.9), followed by dephosphorylation of glucuronic acid 1-phosphate. Glucuronidation is responsible for conjugating potentially toxic lipophilic compounds with glucuronic acid, thereby producing molecules with greater aqueous solubility that is excreted more readily into urine and bile. The rate at which any compound may be glucuronidated depends on the concentration and activity of the UDP-glucuronosyltransferases as well as the concentration of the cofactor UDP-glucuronic acid. UDP-glucuronic acid is formed after oxidation of UDP-glucose by UDP-glucose dehydrogenase (UGDH, EC 1.1.1.22) with NAD as the electron acceptor. UDP-glucuronic acid may then be either used as the glucuronic acid donor for xenobiotic conjugation reactions by UDPglucuronosyltransferases (GlcAT-P, EC 2.4.1.17), or degraded to D-glucuronic acid 1-phosphate after the phosphodiester bond is cleaved by E-NPP3. E-NPP3 is the same enzyme that further reduces D-Glucuronic acid 1-phosphate to free D-glucuronic acid. Decreases in UDP-glucuronic acid concentration may be due to reduced availability of UDP-glucose or decreased UGDH activity or to increased activities of GlcAT-P or E-NPP3. Exposure to volatile anesthetics reduces hepatic UDP-glucuronic acid concentrations, and alters the rate of conjugation of compounds such as acetaminophen, bilirubin, diethylstilbestrol, iopanoic acid and valproic acid in a non-sex-dependent fashion in experimental mice. The depletion of UDP-glucuronic acid by anesthetics is caused by altered activity of microsomal E-NPP3. (PMID: 2167093, 16689937, 1276).

Glucuronic acid sulfate

(3,4,5,6-tetrahydroxyoxane-2-carbonyloxy)sulfonic acid

Iduronate 2-sulfate

2,3,4-Trihydroxy-6-oxo-5-(sulphooxy)hexanoic acid

(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-sulfooxyoxane-2-carboxylic acid

(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-sulphooxyoxane-2-carboxylic acid

6-bromo-1-ethyl-9H-pyrido[3,4-b]indole

C13H11BrN2 (274.0106)

RG-14620

α-[(3,5-dichlorophenyl)methylene]-3-pyridineacetonitrile

C14H8Cl2N2 (274.0065)

Benzyl 4-bromophenyl ketone

2-BROMO-2-PHENYLACETOPHENONE

C14H11BrO (273.9993)

4,7-dichloro-2-phenylquinazoline

C14H8Cl2N2 (274.0065)

3-(2-Chloroactyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide

4-Arsonophenylglycinamide

C8H11AsN2O4 (273.9935)

(E)-3-(3,5-dichlorophenyl)-2-pyridin-3-ylprop-2-enenitrile

C14H8Cl2N2 (274.0065)

2-O-sulfo-beta-D-glucuronic acid

Hexanediol 1,6-bisphosphate

C6H12O8P2-4 (274.0007)

(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-sulfooxyoxane-2-carboxylic acid

D-Glucuronic acid 1-phosphate

A uronic acid phosphate consisting of D-glucuronic acid having a phosphate group attached at the 1-position.

L-iduronic acid 2-sulfate

4-Ketocyclophosphamide

D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D010752 - Phosphoramide Mustards

α-D-Glucuronic acid-1-phosphate

1-Phospho-alpha-D-glucuronic acid