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[ CAS No. 65-22-5 ] {[proInfo.proName]}

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Chemical Structure| 65-22-5
Chemical Structure| 65-22-5
Structure of 65-22-5 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Humberto De Vitto ; Kafi K. J. Belfon ; Nandini Sharma , et al. DOI:

Abstract: Thiamin and its phosphate derivatives are ubiquitous molecules involved as essential cofactors in many cellular processes. The de novo biosynthesis of thiamin employs the parallel synthesis of 4-methyl-5-(2-hydroxyethyl)thiazole (THZ-P) and 4-amino-2-methyl-5(diphosphooxymethyl) pyrimidine (HMP) pyrophosphate (HMP-PP), which are coupled to generate thiamin phosphate. Most organisms that can biosynthesize thiamin employ a kinase (HMPK or ThiD) to generate HMP-PP. In nearly all cases, this enzyme is bifunctional and can also salvage free HMP, producing HMP-P, the monophosphate precursor of HMP-PP. Here we present high-resolution crystal structures of an HMPK from Acinetobacter baumannii (AbHMPK), both unliganded and with pyridoxal 5-phosphate (PLP) noncovalently bound. Despite the similarity between HMPK and pyridoxal kinase enzymes, our kinetics analysis indicates that AbHMPK accepts HMP exclusively as a substrate and cannot turn over , , or nor does it display phosphatase activity. PLP does, however, act as a weak inhibitor of AbHMPK with an IC50 of 768 μM. Surprisingly, unlike other HMPKs, AbHMPK catalyzes only the phosphorylation of HMP and does not generate the diphosphate HMP-PP. This suggests that an additional kinase is present in A. baumannii, or an alternative mechanism is in operation to complete the biosynthesis of thiamin.

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Product Details of [ 65-22-5 ]

CAS No. :65-22-5 MDL No. :MFCD00012809
Formula : C8H10ClNO3 Boiling Point : -
Linear Structure Formula :OCHC5HN(OH)CH3(CH2OH)·HCl InChI Key :FCHXJFJNDJXENQ-UHFFFAOYSA-N
M.W : 203.62 Pubchem ID :6171
Synonyms :
Chemical Name :3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride

Calculated chemistry of [ 65-22-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 49.71
TPSA : 70.42 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 1.05
Log Po/w (MLOGP) : -0.68
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 0.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.402 mg/ml ; 0.00198 mol/l
Class : Soluble
Log S (Ali) : -3.32
Solubility : 0.0967 mg/ml ; 0.000475 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.61
Solubility : 5.02 mg/ml ; 0.0247 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 65-22-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65-22-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 65-22-5 ]

[ 65-22-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 7504-94-1 ]
  • [ 65-22-5 ]
  • (E)-5-(hydroxymethyl)-2-methyl-4-((2-(pyrimidin-2-yl)hydrazono)methyl)pyridin-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% In ethanol; at 20℃; General procedure: The desired compounds 1a-g and 2a-f were prepared by reaction between pyridoxal hydrochloride (0.15 g, 0.74mmol) and the appropriate aromatic or heteroaromatic hydrazine or N-acylhydrazine (1.1 eq., 0.81mmol) in ethanol (10.0 mL). The reaction mixture was stirred for 1-48 hours at room temperature. After that, product was purified by wash-ing with cold ethanol (3.0 mL) and cold diethyl ether (3.0 mL), leading to the pure derivatives 1a-g and 2a-f as solid in 42-86% yields.
  • 2
  • [ 142-71-2 ]
  • [ 65-22-5 ]
  • [ 770-05-8 ]
  • 4Cu(2+)*4C(CH2O)CHNC(CH3)C(O)CCHNCH2CH(C6H4O)O(4-)*8H(1+)=Cu4(C(CH2O)CHNC(CH3)C(OH)CCHNCH2CH(C6H4OH)O)4 [ No CAS ]
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