NAV

Coenzyme A persulfide

Identification

Generic Name
Coenzyme A persulfide
DrugBank Accession Number
DB04036
Background

Coenzyme A persulfide is a possible in vivo inhibitor of mammalian short chain acyl-CoA dehydrogenase.

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 799.599
Monoisotopic: 799.087279055
Chemical Formula
C21H36N7O16P3S2
Synonyms
  • CoA persulfide
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UIsovaleryl-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

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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Coenzyme A and derivatives
Alternative Parents
Purine ribonucleoside diphosphates / Ribonucleoside 3'-phosphates / Pentose phosphates / Beta amino acids and derivatives / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates
show 15 more
Substituents
6-aminopurine / Alcohol / Alkyl phosphate / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Beta amino acid or derivatives
show 42 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
81918-99-2
InChI Key
REVPHPVBPSIEKM-IBOSZNHHSA-N
InChI
InChI=1S/C21H36N7O16P3S2/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-49-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-({2-[(2-disulfanylethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-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])CCSS)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1

References

General References
Not Available
PubChem Compound
174251
PubChem Substance
46504967
ChemSpider
152018
ZINC
ZINC000085432299
PDBe Ligand
COS
PDB Entries
1ivh / 2jif / 2vig / 4l1f / 5ol2

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 Solubility4.26 mg/mLALOGPS
logP-0.43ALOGPS
logP-5.5Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83Chemaxon
pKa (Strongest Basic)4.89Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area346.56 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity168.51 m3·mol-1Chemaxon
Polarizability69.73 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.749
Blood Brain Barrier-0.7458
Caco-2 permeable-0.6891
P-glycoprotein substrateSubstrate0.7769
P-glycoprotein inhibitor INon-inhibitor0.6655
P-glycoprotein inhibitor IINon-inhibitor0.9893
Renal organic cation transporterNon-inhibitor0.9554
CYP450 2C9 substrateNon-substrate0.8277
CYP450 2D6 substrateNon-substrate0.7838
CYP450 3A4 substrateSubstrate0.5823
CYP450 1A2 substrateNon-inhibitor0.8028
CYP450 2C9 inhibitorNon-inhibitor0.8094
CYP450 2D6 inhibitorNon-inhibitor0.8403
CYP450 2C19 inhibitorNon-inhibitor0.7817
CYP450 3A4 inhibitorNon-inhibitor0.7839
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.93
Ames testNon AMES toxic0.6529
CarcinogenicityNon-carcinogens0.8084
BiodegradationNot ready biodegradable0.9836
Rat acute toxicity2.6602 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9373
hERG inhibition (predictor II)Non-inhibitor0.6263
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/MSsplash10-0udi-0000000490-88da298f40ce8533744b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0000000900-43f6eb246636e333822a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ou-1960201500-9a35dded3b5ba6dd20d4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-2400005900-6057d268c659dddfb4a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-ddb494a90c21dfb39dc8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0w59-4100114900-8bdaa0f0ae5e1c3d0bdf
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-288.8614119
predicted
DarkChem Lite v0.1.0
[M-H]-203.85042
predicted
DeepCCS 1.0 (2019)
[M+H]+289.4060119
predicted
DarkChem Lite v0.1.0
[M+H]+205.6745
predicted
DeepCCS 1.0 (2019)
[M+Na]+289.6325119
predicted
DarkChem Lite v0.1.0
[M+Na]+211.2809
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Isovaleryl-CoA dehydrogenase, mitochondrial
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
Not Available
Gene Name
IVD
Uniprot ID
P26440
Uniprot Name
Isovaleryl-CoA dehydrogenase, mitochondrial
Molecular Weight
46319.05 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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52