Methacrylyl-Coenzyme A

Identification

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Name
Methacrylyl-Coenzyme A
Accession Number
DB01675  (EXPT00129)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
6008-91-9
Weight
Average: 835.608
Monoisotopic: 835.141423115
Chemical Formula
C25H40N7O17P3S
InChI Key
NPALUEYCDZWBOV-NDZSKPAWSA-N
InChI
InChI=1S/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19+,23-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
SMILES
CC(=C)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UIsobutyryl-CoA dehydrogenase, mitochondrialNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C03460
PubChem Compound
165390
PubChem Substance
46507414
ChemSpider
144985
ChEBI
27754
HET
2MC
PDB Entries
1rx0

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.11 mg/mLALOGPS
logP-0.38ALOGPS
logP-5.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity181.21 m3·mol-1ChemAxon
Polarizability72.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5204
Blood Brain Barrier-0.7983
Caco-2 permeable-0.6595
P-glycoprotein substrateSubstrate0.828
P-glycoprotein inhibitor INon-inhibitor0.5224
P-glycoprotein inhibitor IINon-inhibitor0.9455
Renal organic cation transporterNon-inhibitor0.958
CYP450 2C9 substrateNon-substrate0.8316
CYP450 2D6 substrateNon-substrate0.7999
CYP450 3A4 substrateSubstrate0.6159
CYP450 1A2 substrateNon-inhibitor0.7777
CYP450 2C9 inhibitorNon-inhibitor0.764
CYP450 2D6 inhibitorNon-inhibitor0.8561
CYP450 2C19 inhibitorNon-inhibitor0.7232
CYP450 3A4 inhibitorNon-inhibitor0.7014
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8931
Ames testNon AMES toxic0.6061
CarcinogenicityNon-carcinogens0.8287
BiodegradationNot ready biodegradable0.9904
Rat acute toxicity2.6671 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9274
hERG inhibition (predictor II)Non-inhibitor0.5974
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acyl thioesters
Direct Parent
Acyl CoAs
Alternative Parents
Coenzyme A and derivatives / Purine ribonucleoside diphosphates / Pentose phosphates / Ribonucleoside 3'-phosphates / Beta amino acids and derivatives / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives
show 18 more
Substituents
Coenzyme a or derivatives / Purine ribonucleoside 3',5'-bisphosphate / Purine ribonucleoside bisphosphate / Purine ribonucleoside diphosphate / Ribonucleoside 3'-phosphate / Pentose phosphate / Pentose-5-phosphate / Beta amino acid or derivatives / Glycosyl compound / N-glycosyl compound
show 46 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
acyl-CoA (CHEBI:27754)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-ch group of donors, with a flavin as acceptor
Specific Function
Has very high activity toward isobutyryl-CoA. Is an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Plays a role in transcriptional coactivation within the ARC complex.
Gene Name
ACAD8
Uniprot ID
Q9UKU7
Uniprot Name
Isobutyryl-CoA dehydrogenase, mitochondrial
Molecular Weight
45069.39 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:21