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Identification
NameAcetoacetyl-Coenzyme A
Accession NumberDB03059  (EXPT00820)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS number1420-36-6
WeightAverage: 851.607
Monoisotopic: 851.136337737
Chemical FormulaC25H40N7O18P3S
InChI KeyInChIKey=OJFDKHTZOUZBOS-YTJNUSSGSA-N
InChI
InChI=1S/C25H40N7O18P3S/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/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18+,19-,20+,24+/m0/s1
IUPAC Name
{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3S)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]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)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H]1O[[email protected]]([[email protected]](O)[[email protected]]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-oxo-acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ketone
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.83 mg/mLALOGPS
logP-0.37ALOGPS
logP-6.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity182.1 m3·mol-1ChemAxon
Polarizability75.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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
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 ]
Kind
Protein
Organism
Zoogloea ramigera
Pharmacological action
unknown
General Function:
Acetyl-coa c-acetyltransferase activity
Specific Function:
Not Available
Gene Name:
phbA
Uniprot ID:
P07097
Molecular Weight:
40472.955 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Flavin adenine dinucleotide binding
Specific Function:
Introduces a double bond at position 2 in saturated acyl-CoA's of short chain length, i.e. less than 6 carbon atoms.
Gene Name:
ACADS
Uniprot ID:
P16219
Molecular Weight:
44296.705 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 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Enoyl-coa hydratase activity
Specific Function:
Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:
ECHS1
Uniprot ID:
P30084
Molecular Weight:
31387.085 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 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Involved in catalytic activity
Specific Function:
Not Available
Gene Name:
menB
Uniprot ID:
O06414
Molecular Weight:
34689.0 Da
Kind
Protein
Organism
Megasphaera elsdenii
Pharmacological action
unknown
General Function:
Flavin adenine dinucleotide binding
Specific Function:
Has an optimum specificity for 4-carbon length fatty acyl-CoAs.
Gene Name:
Not Available
Uniprot ID:
Q06319
Molecular Weight:
41407.87 Da
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
unknown
General Function:
Hydroxymethylglutaryl-coa synthase activity
Specific Function:
Not Available
Gene Name:
mvaS
Uniprot ID:
Q9FD87
Molecular Weight:
43217.195 Da
Kind
Protein
Organism
Staphylococcus aureus (strain MW2)
Pharmacological action
unknown
General Function:
Involved in hydroxymethylglutaryl-CoA synthase activity
Specific Function:
Not Available
Gene Name:
mvaS
Uniprot ID:
Q79ZY6
Molecular Weight:
43206.0 Da
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19