NAV

4-hydroxybenzyl coenzyme A

Identification

Generic Name
4-hydroxybenzyl coenzyme A
DrugBank Accession Number
DB04067
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 873.656
Monoisotopic: 873.157073179
Chemical Formula
C28H42N7O17P3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U4-hydroxybenzoyl-CoA thioesteraseNot AvailableArthrobacter sp.
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as s-alkyl-coas. These are alkyl sulfides consisting of coenzyme A that carries an S-alkyl substituent.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
S-alkyl-CoAs
Sub Class
Not Available
Direct Parent
S-alkyl-CoAs
Alternative Parents
Coenzyme A and derivatives / Purine ribonucleoside diphosphates / Pentose phosphates / Ribonucleoside 3'-phosphates / Beta amino acids and derivatives / Glycosylamines / 6-aminopurines / Organic pyrophosphates / Monosaccharide phosphates / Aminopyrimidines and derivatives
show 19 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole
show 50 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FZQUTWRNQJPTSH-SXQYHYLKSA-N
InChI
InChI=1S/C28H42N7O17P3S/c1-28(2,23(39)26(40)31-8-7-19(37)30-9-10-56-12-16-3-5-17(36)6-4-16)13-49-55(46,47)52-54(44,45)48-11-18-22(51-53(41,42)43)21(38)27(50-18)35-15-34-20-24(29)32-14-33-25(20)35/h3-6,14-15,18,21-23,27,36,38-39H,7-13H2,1-2H3,(H,30,37)(H,31,40)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t18-,21-,22-,23+,27-/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-hydroxyphenyl)methyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
SMILES
[H]N([H])C1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)N([H])CCC(=O)N([H])CCSCC4=CC=C(O)C=C4)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1

References

General References
Not Available
PubChem Compound
446969
PubChem Substance
46505458
ChemSpider
394188
ZINC
ZINC000195757461
PDBe Ligand
4CA
PDB Entries
1lo8 / 1q4u

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility3.34 mg/mLALOGPS
logP-0.28ALOGPS
logP-4.2Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83Chemaxon
pKa (Strongest Basic)4.89Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count17Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area366.79 Å2Chemaxon
Rotatable Bond Count21Chemaxon
Refractivity194.03 m3·mol-1Chemaxon
Polarizability79.34 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8738
Blood Brain Barrier-0.8453
Caco-2 permeable-0.7061
P-glycoprotein substrateSubstrate0.8586
P-glycoprotein inhibitor INon-inhibitor0.6332
P-glycoprotein inhibitor IINon-inhibitor0.9858
Renal organic cation transporterNon-inhibitor0.937
CYP450 2C9 substrateNon-substrate0.7937
CYP450 2D6 substrateNon-substrate0.7776
CYP450 3A4 substrateSubstrate0.6479
CYP450 1A2 substrateNon-inhibitor0.8251
CYP450 2C9 inhibitorNon-inhibitor0.8131
CYP450 2D6 inhibitorNon-inhibitor0.8095
CYP450 2C19 inhibitorNon-inhibitor0.8189
CYP450 3A4 inhibitorNon-inhibitor0.6077
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8824
Ames testNon AMES toxic0.6723
CarcinogenicityNon-carcinogens0.7948
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5810 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.874
hERG inhibition (predictor II)Inhibitor0.6128
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/MSsplash10-00di-0000000190-fdd8cc9d65fdca63c845
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000000490-93056b0d00fba6b6ce0d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0cmi-0617400790-c878e476f5af65cb6fd2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-006t-5410102690-763189a37c2b79429927
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0109000000-c304041c12b325ef0418
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-3500132940-1feaae46a9f3b1886c81
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-218.58803
predicted
DeepCCS 1.0 (2019)
[M+H]+220.29929
predicted
DeepCCS 1.0 (2019)
[M+Na]+226.398
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 4-hydroxybenzoyl-CoA thioesterase
Kind
Protein
Organism
Arthrobacter sp.
Pharmacological action
Unknown
General Function
4-hydroxybenzoyl-coa thioesterase activity
Specific Function
Not Available
Gene Name
fcbC
Uniprot ID
Q04416
Uniprot Name
4-hydroxybenzoyl-CoA thioesterase
Molecular Weight
16394.32 Da
Details2. 4-hydroxybenzoyl-CoA thioesterase
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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52