4-hydroxybenzoyl-CoA

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
4-hydroxybenzoyl-CoA
Accession Number
DB01652  (EXPT00637)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 4-hydroxybenzoyl coenzyme A
  • 4-hydroxybenzoyl-CoA
  • 4-hydroxybenzoyl-coenzyme A
  • p-hydroxybenzoyl-CoA
  • p-hydroxybenzoyl-coenzyme A
Categories
UNII
Not Available
CAS number
27718-41-8
Weight
Average: 887.64
Monoisotopic: 887.136337737
Chemical Formula
C28H40N7O18P3S
InChI Key
LTVXPVBFJBTNIJ-TYHXJLICSA-N
InChI
InChI=1S/C28H40N7O18P3S/c1-28(2,22(39)25(40)31-8-7-18(37)30-9-10-57-27(41)15-3-5-16(36)6-4-15)12-50-56(47,48)53-55(45,46)49-11-17-21(52-54(42,43)44)20(38)26(51-17)35-14-34-19-23(29)32-13-33-24(19)35/h3-6,13-14,17,20-22,26,36,38-39H,7-12H2,1-2H3,(H,30,37)(H,31,40)(H,45,46)(H,47,48)(H2,29,32,33)(H2,42,43,44)/t17-,20-,21-,22+,26-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-[(2-{[2-(4-hydroxybenzoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
SMILES
CC(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)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U4-chlorobenzoyl CoA dehalogenaseNot AvailablePseudomonas sp. DJ-12
U4-hydroxybenzoyl-CoA thioesteraseNot AvailablePseudomonas sp. (strain CBS-3)
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

Synthesis Reference

Robert Christopher Brown, Rekha Seshadri, Carlos Chavez-Torres, Weidong Xu, Toby Richardson, "GENETICALLY ENGINEERED MICROORGANISMS COMPRISING 4-HYDROXYBENZOYL-COA THIOESTERASES AND METHODS OF USING THE SAME FOR PRODUCING FREE FATTY ACIDS AND FATTY ACID DERIVATIVES." U.S. Patent US20120164713, issued June 28, 2012.

US20120164713
General References
Not Available
External Links
Human Metabolome Database
HMDB0060140
KEGG Compound
C02949
PubChem Compound
168718
PubChem Substance
46505693
ChemSpider
147584
ChEBI
15500
HET
BCA
Wikipedia
4-hydroxybenzoyl-CoA_reductase
PDB Entries
1jxz / 1lo9 / 1nzy

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 Solubility3.28 mg/mLALOGPS
logP0.01ALOGPS
logP-4.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.89ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity194.86 m3·mol-1ChemAxon
Polarizability79.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.777
Blood Brain Barrier-0.8259
Caco-2 permeable-0.7147
P-glycoprotein substrateSubstrate0.8044
P-glycoprotein inhibitor INon-inhibitor0.6914
P-glycoprotein inhibitor IINon-inhibitor0.9838
Renal organic cation transporterNon-inhibitor0.9383
CYP450 2C9 substrateNon-substrate0.7383
CYP450 2D6 substrateNon-substrate0.7856
CYP450 3A4 substrateSubstrate0.6248
CYP450 1A2 substrateNon-inhibitor0.8289
CYP450 2C9 inhibitorNon-inhibitor0.7719
CYP450 2D6 inhibitorNon-inhibitor0.8212
CYP450 2C19 inhibitorNon-inhibitor0.7822
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8481
Ames testNon AMES toxic0.6526
CarcinogenicityNon-carcinogens0.7919
BiodegradationNot ready biodegradable0.9974
Rat acute toxicity2.6138 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9473
hERG inhibition (predictor II)Inhibitor0.5788
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 / Ribonucleoside 3'-phosphates / Pentose phosphates / Beta amino acids and derivatives / Glycosylamines / 6-aminopurines / Organic pyrophosphates / Monosaccharide phosphates / Thiobenzoic acids and derivatives
show 22 more
Substituents
Coenzyme a or derivatives / Purine ribonucleoside diphosphate / Purine ribonucleoside bisphosphate / Purine ribonucleoside 3',5'-bisphosphate / Pentose-5-phosphate / Ribonucleoside 3'-phosphate / Pentose phosphate / Beta amino acid or derivatives / Glycosyl compound / N-glycosyl compound
show 53 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
hydroxybenzoyl-CoA (CHEBI:15500)

Targets

Kind
Protein
Organism
Pseudomonas sp. DJ-12
Pharmacological action
Unknown
General Function
Catalytic activity
Specific Function
Not Available
Gene Name
fcbB
Uniprot ID
O68600
Uniprot Name
4-chlorobenzoyl CoA dehalogenase
Molecular Weight
29805.98 Da
Kind
Protein
Organism
Pseudomonas sp. (strain CBS-3)
Pharmacological action
Unknown
General Function
4-hydroxybenzoyl-coa thioesterase activity
Specific Function
Hydrolyzes 4-hydroxybenzoate-CoA, and to a lesser extent benzoyl-CoA and 4-chlorobenzoate-CoA. Not active against aliphatic acyl-CoA thioesters, including palmitoyl-CoA, hexanoyl-CoA and acetyl-CoA.
Gene Name
Not Available
Uniprot ID
P56653
Uniprot Name
4-hydroxybenzoyl-CoA thioesterase
Molecular Weight
16105.3 Da

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