Pyridoxal phosphate

Names

[ CAS No. ]:
54-47-7

[ Name ]:
Pyridoxal phosphate

[Synonym ]:
Pyridoxal-5-monophosphate
(4-Formyl-5-hydroxy-6-methyl-3-pyridinyl)methyl dihydrogen phosphate
Phosphate, Pyridoxal
(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate
(4-Formyl-5-hydroxy-6-methyl-3-pyridinyl)methyldihydrogen-phosphat
Aderoxal
EINECS 200-208-3
Pyridoxal phosphate (6CI)
(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyldihydrogen-phosphat
Vitamin B6 phosphate
Pyridoxal 5-phosphate
Pyridoxal phosphate
MFCD00006333
4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[ (phosphonooxy)methyl]-
Pyridoxyl phosphate
Pyridoxal 5'-phosphic acid
Isonicotinaldehyde, 3-hydroxy-5-(hydroxymethyl)-2-methyl-, 5-(dihydrogen phosphate)
4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-
3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde

Biological Activity

[Description]:

Pyridoxal phosphate is the active form of vitamin B6, acts as an inhibitor of reverse transcriptases, and is used for the treatment of tardive dyskinesia.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Reverse Transcriptase

Research Areas >> Neurological Disease

Natural Products >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

Pyridoxal 5′-phosphate severely inhibits the DNA Polymerase and RNase H. Pyridoxal phosphate results in an imnediate reduction in the rate of DNA synthesis[1]. Conjugation to pyridoxal phosphate fully inhibits NEIL2. Pyridoxal phosphate-conjugated NEIL2 shows much lower activity than the intact enzyme over a wide range of enzyme/substrate ratios. After Pyridoxal phosphate conjugation, the ability of NEIL2 to bind the THF-ligand is completely lost[2].

[References]

[1]. Modak MJ. Pyridoxal 5' phosphate: a selective inhibitor of oncornaviral DNA polymerases. Biochem Biophys Res Commun. 1976 Jul 12;71(1):180-7.

[2]. Grin IR, et al. Inactivation of NEIL2 DNA glycosylase by pyridoxal phosphate reveals a loop important for substrate binding. Biochem Biophys Res Commun. 2010 Mar 26;394(1):100-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
565.7±60.0 °C at 760 mmHg

[ Melting Point ]:
140-143ºC

[ Molecular Formula ]:
C₈H₁₀NO₆P

[ Molecular Weight ]:
247.142

[ Flash Point ]:
296.0±32.9 °C

[ Exact Mass ]:
247.024567

[ PSA ]:
126.76000

[ LogP ]:
-0.52

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.641

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UV1207000

CHEMICAL NAME :: Pyridoxal, 5-(dihydrogen phosphate)

CAS REGISTRY NUMBER :: 54-47-7

LAST UPDATED :: 199701

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C8-H10-N-O6-P

MOLECULAR WEIGHT :: 247.16

WISWESSER LINE NOTATION :: T6NJ B1 CQ DVH E1OPQQO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 850 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4640 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 870 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 530 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1150 mg/kg

TOXIC EFFECTS :: Behavioral - antipsychotic

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 50 umol/L

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 34,530,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3949 No. of Facilities: 577 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 5538 (estimated) No. of Female Employees: 3978 (estimated)

Safety Information

[ Safety Phrases ]:
22-24/25

[ WGK Germany ]:
3

[ HS Code ]:
2936250000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%