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[ CAS No. 2438-05-3 ] {[proInfo.proName]}

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Chemical Structure| 2438-05-3
Chemical Structure| 2438-05-3
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Product Citations

Product Citations

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. DOI: PubMed ID:

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ～35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

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Product Details of [ 2438-05-3 ]

CAS No. :2438-05-3 MDL No. :MFCD00013996
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :CH3CH2CH2C6H4CO2H InChI Key :ATZHGRNFEFVDDJ-UHFFFAOYSA-N
M.W : 164.20 Pubchem ID :137601
Synonyms :

Calculated chemistry of [ 2438-05-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.98
TPSA : 37.3 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 3.42
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 2.55
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 2.53

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.107 mg/ml ; 0.000654 mol/l
Class : Soluble
Log S (Ali) : -3.88
Solubility : 0.0215 mg/ml ; 0.000131 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.181 mg/ml ; 0.0011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 2438-05-3 ]

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

Application In Synthesis of [ 2438-05-3 ]

* 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 [ 2438-05-3 ]

[ 2438-05-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 2932-65-2 ]
  • [ 2438-05-3 ]
  • 2
  • [ 2438-05-3 ]
  • [ 28785-06-0 ]
YieldReaction ConditionsOperation in experiment
REFERENCE EXAMPLE 9 4-Propylbenzaldehyde Following a similar procedure to that described in reference example 7, but starting from 4-propylbenzoic acid instead of piperonylic acid, the title compound of the example was obtained as an oil. 1H-NMR (300 MHz, CDCl3 delta TMS): 0.98 (t, J=7 Hz, 3H), 1.68 (m, 2H), 2.67 (t, J=7 Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 7.80 (d, J=8.4 Hz, 2H), 9.98 (s, 1H).
  • 3
  • sodium metabisulfite [ No CAS ]
  • [ 2932-65-2 ]
  • [ 2438-05-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; bromine; In 1,4-dioxane; water; Step B1: The production of 4-n-propylbenzoic acid A solution of sodium hypobromite prepared by dissolving bromine (1.0 mole) in a solution of sodium hydroxide (3.5 mole) in water (700 ml) at 0 C. was added to a well stirred solution of 4-n-propylacetophenone (0.2 mole), prepared in step A1, in dioxan (500 ml). Throughout the addition and for 0.25 hours afterwards the temperature was maintained at 35-45 C. The excess of sodium hypobromite wad destroyed by adding a solution of sodium metabisulphite. Water (3.5 L) was added and bromoform distilled from the reation mixture. On cooling, the solution was acidified with concentrated hydrochloric acid and the precipitated product filtered off and washed with water. The product was crystallized from ethanol/water to yield white crystals mpt 141.2 C.
  • 4
  • [ 28785-06-0 ]
  • [ 2438-05-3 ]
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