Acetoacetyl-CoA

Identification

Name
Acetoacetyl-CoA
Accession Number
DB03059  (EXPT00820)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 3-Acetoacetyl-CoA
  • Acetoacetyl coenzyme A
  • Acetoacetyl-Coenzyme A
  • S-acetoacetyl-CoA
  • S-Acetoacetyl-coenzym A
  • S-acetoacetyl-coenzyme A
Categories
UNII
Not Available
CAS number
1420-36-6
Weight
Average: 851.607
Monoisotopic: 851.136337737
Chemical Formula
C25H40N7O18P3S
InChI Key
OJFDKHTZOUZBOS-CITAKDKDSA-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-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-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)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
U1,4-Dihydroxy-2-naphthoyl-CoA synthaseNot AvailableMycobacterium tuberculosis
UAcyl-CoA dehydrogenase, short-chain specificNot AvailableMegasphaera elsdenii
UHMG-CoA synthaseNot AvailableStaphylococcus aureus
U3-hydroxy-3-methylglutaryl CoA synthaseNot AvailableStaphylococcus aureus (strain MW2)
UHydroxyacyl-coenzyme A dehydrogenase, mitochondrialNot AvailableHuman
UAcetyl-CoA acetyltransferaseNot AvailableZoogloea ramigera
UShort-chain specific acyl-CoA dehydrogenase, mitochondrialNot AvailableHuman
UEnoyl-CoA hydratase, mitochondrialNot AvailableHuman
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
KEGG Compound
C00332
PubChem Compound
92153
PubChem Substance
46506303
ChemSpider
83198
ChEBI
15345
HET
CAA
Wikipedia
Acetoacetyl-CoA
PDB Entries
1buc / 1dub / 1ee0 / 1f0y / 1il0 / 1jqi / 1m1o / 1m75 / 1m76 / 1q51
show 20 more

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 Solubility3.83 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
Polarizability75.74 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/MSsplash10-000i-1912000130-163ca7231778bddd9739
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0913000000-4f4f26abcf9b0d9f285e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2911000000-cc9acdeb298fa6ebbdb7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9730140350-cefdc8a0886f8e9e2b86
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-5910110010-51e3282fd98f872b9ff5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-057i-6900100000-4a6e405bfbd488ea01d4

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acyl thioesters
Direct Parent
3-oxo-acyl CoAs
Alternative Parents
Coenzyme A and derivatives / Purine ribonucleoside diphosphates / Pentose phosphates / Ribonucleoside 3'-phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates
show 19 more
Substituents
Coenzyme a or derivatives / Purine ribonucleoside diphosphate / Purine ribonucleoside bisphosphate / Purine ribonucleoside 3',5'-bisphosphate / Ribonucleoside 3'-phosphate / Pentose-5-phosphate / Pentose phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine
show 47 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
3-oxo-fatty acyl-CoA (CHEBI:15345)

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Converts o-succinylbenzoyl-CoA (OSB-CoA) to 1,4-dihydroxy-2-naphthoyl-CoA (DHNA-CoA).
Specific Function
1,4-dihydroxy-2-naphthoyl-coa synthase activity
Gene Name
menB
Uniprot ID
P9WNP5
Uniprot Name
1,4-dihydroxy-2-naphthoyl-CoA synthase
Molecular Weight
34688.715 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
Uniprot Name
Acyl-CoA dehydrogenase, short-chain specific
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
Uniprot Name
HMG-CoA synthase
Molecular Weight
43217.195 Da
Kind
Protein
Organism
Staphylococcus aureus (strain MW2)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Hydroxymethylglutaryl-coa synthase activity
Gene Name
mvaS
Uniprot ID
A0A0H3K1U2
Uniprot Name
3-hydroxy-3-methylglutaryl CoA synthase
Molecular Weight
43205.095 Da
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
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]
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
Uniprot Name
Acetyl-CoA acetyltransferase
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
Uniprot Name
Short-chain specific acyl-CoA dehydrogenase, mitochondrial
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
Uniprot Name
Enoyl-CoA hydratase, mitochondrial
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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:28