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Dodecyl-Coa

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Data Packages
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Overview

Structure
DrugBank ID
DB03264
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
Dodecyl-Coa
DrugBank Accession Number
DB03264
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 949.837
Monoisotopic: 949.282273691
Chemical Formula
C33H58N7O17P3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-oxoacyl-[acyl-carrier-protein] synthase 3Not AvailableMycobacterium tuberculosis
UFatty acid metabolism regulator proteinNot AvailableBacillus subtilis (strain 168)
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
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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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acyl thioesters
Direct Parent
2,3,4-saturated fatty acyl CoAs
Alternative Parents
Medium-chain fatty acyl CoAs / Coenzyme A and derivatives / Purine ribonucleoside diphosphates / Ribonucleoside 3'-phosphates / Pentose phosphates / Beta amino acids and derivatives / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Organic pyrophosphates
show 19 more
Substituents
6-aminopurine / Alcohol / Alkyl phosphate / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Beta amino acid or derivatives
show 46 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
medium-chain fatty acyl-CoA (CHEBI:15521)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
YMCXGHLSVALICC-GMHMEAMDSA-N
InChI
InChI=1S/C33H58N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h20-22,26-28,32,43-44H,4-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/t22-,26-,27-,28+,32-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(dodecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
SMILES
CCCCCCCCCCCC(=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=C(N)N=CN=C12

References

General References
Not Available
Human Metabolome Database
HMDB0003571
PubChem Compound
165436
PubChem Substance
46507209
ChemSpider
145018
ChEBI
15521
ZINC
ZINC000096014531
PDBe Ligand
DCC
PDB Entries
1u6s / 1vi0 / 3ang / 3anp / 3whb / 4ku5 / 6el2

Clinical Trials

Clinical Trials
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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 Solubility2.59 mg/mLALOGPS
logP1.35ALOGPS
logP-1.4Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.83Chemaxon
pKa (Strongest Basic)4.89Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count17Chemaxon
Hydrogen Donor Count9Chemaxon
Polar Surface Area363.63 Å2Chemaxon
Rotatable Bond Count30Chemaxon
Refractivity218.24 m3·mol-1Chemaxon
Polarizability91.94 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8417
Blood Brain Barrier-0.8345
Caco-2 permeable-0.6872
P-glycoprotein substrateSubstrate0.8244
P-glycoprotein inhibitor INon-inhibitor0.6291
P-glycoprotein inhibitor IINon-inhibitor0.9712
Renal organic cation transporterNon-inhibitor0.9671
CYP450 2C9 substrateNon-substrate0.7881
CYP450 2D6 substrateNon-substrate0.799
CYP450 3A4 substrateSubstrate0.5802
CYP450 1A2 substrateNon-inhibitor0.7998
CYP450 2C9 inhibitorNon-inhibitor0.756
CYP450 2D6 inhibitorNon-inhibitor0.8244
CYP450 2C19 inhibitorNon-inhibitor0.734
CYP450 3A4 inhibitorNon-inhibitor0.6679
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9108
Ames testNon AMES toxic0.6223
CarcinogenicityNon-carcinogens0.7947
BiodegradationNot ready biodegradable0.9932
Rat acute toxicity2.7032 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9749
hERG inhibition (predictor II)Non-inhibitor0.5476
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-052b-8302198300-02a363fdd86e4aa3eee2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-3110000009-9ad1be9ff3ae3189f240
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0000000109-bcb01f2a682b9198e251
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a5c-9130100186-36536009a94bb5864b66
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0032-5100402907-92cbb88e5ecf86fadbcb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0000900000-f8f94bf8895cb0f0fa47
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001j-0100111739-8517a1d69ece42324be8
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-345.4504773
predicted
DarkChem Lite v0.1.0
[M-H]-342.7995773
predicted
DarkChem Lite v0.1.0
[M-H]-359.8224773
predicted
DarkChem Lite v0.1.0
[M-H]-231.38892
predicted
DeepCCS 1.0 (2019)
[M+H]+346.1570773
predicted
DarkChem Lite v0.1.0
[M+H]+342.3699773
predicted
DarkChem Lite v0.1.0
[M+H]+358.3369773
predicted
DarkChem Lite v0.1.0
[M+H]+233.04204
predicted
DeepCCS 1.0 (2019)
[M+Na]+347.0467773
predicted
DarkChem Lite v0.1.0
[M+Na]+342.0879773
predicted
DarkChem Lite v0.1.0
[M+Na]+359.0229773
predicted
DarkChem Lite v0.1.0
[M+Na]+239.57637
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-oxoacyl-[acyl-carrier-protein] synthase 3
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Catalyzes the first condensation reaction which initiates fatty acid synthesis and may therefore play a role in governing the total rate of fatty acid production. Possesses both acetoacetyl-ACP synthase and acetyl transacylase activities (PubMed:10840036, PubMed:11278743, PubMed:16040614). Possesses a clear preference for long-chain acyl-CoA substrates rather than acyl-ACP primers. Its substrate specificity determines the biosynthesis of mycolic acid fatty acid chain, which is characteristic of mycobacterial cell wall (PubMed:10840036, PubMed:11278743, PubMed:16040614). In vitro, when AcpM (the natural partner) is used as the carrier, malonate incorporation increases with acyl chain length to reach an apparent maximum with primers ranging in length from C:14-CoA to C:20-CoA (PubMed:16040614). However, the initial acylation step shows preference for dodecanoyl-CoA, suggesting a role for AcpM in determining the specificity of the mtFabH reaction (PubMed:18096200). Shows only very weak activity with acetyl-CoA (PubMed:10840036, PubMed:11278743).
Specific Function
3-oxoacyl-[acyl-carrier-protein] synthase activity
Gene Name
fabH
Uniprot ID
P9WNG3
Uniprot Name
3-oxoacyl-[acyl-carrier-protein] synthase 3
Molecular Weight
34872.13 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]
Details2. Fatty acid metabolism regulator protein
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Transcriptional regulator in fatty acid degradation. Represses transcription of genes required for fatty acid transport and beta-oxidation, including acdA, fadA, fadB, fadE, fadF, fadG, fadH, fadM, fadN, lcfA and lcfB. Binding of FadR to DNA is specifically inhibited by long chain fatty acyl-CoA compounds of 14-20 carbon atoms in length.
Specific Function
DNA-binding transcription factor activity
Gene Name
fadR
Uniprot ID
P94548
Uniprot Name
Fatty acid metabolism regulator protein
Molecular Weight
21978.335 Da

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