3-Hydroxybutyryl-Coenzyme A

Identification

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Name
3-Hydroxybutyryl-Coenzyme A
Accession Number
DB03612  (EXPT00172)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 853.62
Monoisotopic: 853.151989708
Chemical Formula
C25H42N7O18P3S
InChI Key
QHHKKMYHDBRONY-RMNRSTNRSA-N
InChI
InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13?,14-,18-,19-,20+,24-/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-[(3-hydroxybutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
SMILES
CC(O)CC(=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
UHydroxyacyl-coenzyme A 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
PubChem Compound
644065
PubChem Substance
46509071
ChemSpider
559120
ChEBI
37050
HET
3HC

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 Solubility4.07 mg/mLALOGPS
logP-0.62ALOGPS
logP-6.1ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity183.03 m3·mol-1ChemAxon
Polarizability74.71 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7176
Blood Brain Barrier-0.8246
Caco-2 permeable-0.7061
P-glycoprotein substrateSubstrate0.7482
P-glycoprotein inhibitor INon-inhibitor0.6514
P-glycoprotein inhibitor IINon-inhibitor0.977
Renal organic cation transporterNon-inhibitor0.9638
CYP450 2C9 substrateNon-substrate0.7645
CYP450 2D6 substrateNon-substrate0.7814
CYP450 3A4 substrateSubstrate0.5949
CYP450 1A2 substrateNon-inhibitor0.8276
CYP450 2C9 inhibitorNon-inhibitor0.7918
CYP450 2D6 inhibitorNon-inhibitor0.8437
CYP450 2C19 inhibitorNon-inhibitor0.7752
CYP450 3A4 inhibitorNon-inhibitor0.672
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9151
Ames testNon AMES toxic0.6354
CarcinogenicityNon-carcinogens0.8122
BiodegradationNot ready biodegradable0.9934
Rat acute toxicity2.6090 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9605
hERG inhibition (predictor II)Non-inhibitor0.5632
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 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acyl thioesters
Direct Parent
3-hydroxyacyl 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
3-hydroxyacyl-CoA, hydroxybutanoyl-CoA (CHEBI:37050)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nad+ binding
Specific Function
Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name
HADH
Uniprot ID
Q16836
Uniprot Name
Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial
Molecular Weight
34293.275 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 05:53