Acetoacetyl-CoA
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Identification
- Generic Name
- Acetoacetyl-CoA
- DrugBank Accession Number
- DB03059
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 851.607
Monoisotopic: 851.136337737 - Chemical Formula
- C25H40N7O18P3S
- Synonyms
- 3-Acetoacetyl-CoA
- Acetoacetyl coenzyme A
- Acetoacetyl-Coenzyme A
- S-acetoacetyl-CoA
- S-Acetoacetyl-coenzym A
- S-acetoacetyl-coenzyme A
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHydroxyacyl-coenzyme A dehydrogenase, mitochondrial Not Available Humans UAcetyl-CoA acetyltransferase Not Available Zoogloea ramigera UShort-chain specific acyl-CoA dehydrogenase, mitochondrial Not Available Humans UEnoyl-CoA hydratase, mitochondrial Not Available Humans U1,4-Dihydroxy-2-naphthoyl-CoA synthase Not Available Mycobacterium tuberculosis UAcyl-CoA dehydrogenase, short-chain specific Not Available Megasphaera elsdenii UHMG-CoA synthase Not Available Staphylococcus aureus U3-hydroxy-3-methylglutaryl CoA synthase Not Available Staphylococcus aureus (strain MW2) - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- 1,3-dicarbonyl compound / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole show 47 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 3-oxo-fatty acyl-CoA (CHEBI:15345)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 1420-36-6
- 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
References
- General References
- Not Available
- External Links
- KEGG Compound
- C00332
- PubChem Compound
- 92153
- PubChem Substance
- 46506303
- ChemSpider
- 83198
- ChEBI
- 15345
- ZINC
- ZINC000096014521
- PDBe Ligand
- CAA
- Wikipedia
- Acetoacetyl-CoA
- PDB Entries
- 1buc / 1dub / 1ee0 / 1f0y / 1il0 / 1jqi / 1m1o / 1m75 / 1m76 / 1q51 … show 21 more
Clinical Trials
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
Property Value Source Water Solubility 3.83 mg/mL ALOGPS logP -0.37 ALOGPS logP -5.8 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 0.83 Chemaxon pKa (Strongest Basic) 4.89 Chemaxon Physiological Charge -4 Chemaxon Hydrogen Acceptor Count 18 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 380.7 Å2 Chemaxon Rotatable Bond Count 22 Chemaxon Refractivity 182.1 m3·mol-1 Chemaxon Polarizability 76.33 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7176 Blood Brain Barrier - 0.8246 Caco-2 permeable - 0.7061 P-glycoprotein substrate Substrate 0.7482 P-glycoprotein inhibitor I Non-inhibitor 0.6514 P-glycoprotein inhibitor II Non-inhibitor 0.977 Renal organic cation transporter Non-inhibitor 0.9638 CYP450 2C9 substrate Non-substrate 0.7645 CYP450 2D6 substrate Non-substrate 0.7814 CYP450 3A4 substrate Substrate 0.5949 CYP450 1A2 substrate Non-inhibitor 0.8276 CYP450 2C9 inhibitor Non-inhibitor 0.7918 CYP450 2D6 inhibitor Non-inhibitor 0.8437 CYP450 2C19 inhibitor Non-inhibitor 0.7752 CYP450 3A4 inhibitor Non-inhibitor 0.672 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9151 Ames test Non AMES toxic 0.6354 Carcinogenicity Non-carcinogens 0.8122 Biodegradation Not ready biodegradable 0.9934 Rat acute toxicity 2.6090 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9605 hERG inhibition (predictor II) Non-inhibitor 0.5632
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 207.681 predictedDeepCCS 1.0 (2019) [M+H]+ 209.3342 predictedDeepCCS 1.0 (2019) [M+Na]+ 216.36467 predictedDeepCCS 1.0 (2019)
Targets
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- 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
2. DetailsAcetyl-CoA acetyltransferase
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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. [Article]
4. DetailsEnoyl-CoA hydratase, mitochondrial
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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. [Article]
5. Details1,4-Dihydroxy-2-naphthoyl-CoA synthase
- 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
7. DetailsHMG-CoA synthase
- 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
8. Details3-hydroxy-3-methylglutaryl CoA synthase
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52