3-Acetylpyridine Adenine Dinucleotide

Identification

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Name
3-Acetylpyridine Adenine Dinucleotide
Accession Number
DB03363  (EXPT00368, EXPT02282, DB03969)
Type
Small Molecule
Groups
Experimental
Description

A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed)

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 662.437
Monoisotopic: 662.113872658
Chemical Formula
C22H28N6O14P2
InChI Key
KPVQNXLUPNWQHM-RBEMOOQDSA-N
InChI
InChI=1S/C22H28N6O14P2/c1-10(29)11-3-2-4-27(5-11)21-17(32)15(30)12(40-21)6-38-43(34,35)42-44(36,37)39-7-13-16(31)18(33)22(41-13)28-9-26-14-19(23)24-8-25-20(14)28/h2-5,8-9,12-13,15-18,21-22,30-33H,6-7H2,1H3,(H3-,23,24,25,34,35,36,37)/t12-,13-,15-,16-,17-,18-,21-,22-/m1/s1
IUPAC Name
3-acetyl-1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-1λ⁵-pyridin-1-ylium
SMILES
[H][C@]1(COP([O-])(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])([N+]3=CC=CC(=C3)C(C)=O)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U4-hydroxy-tetrahydrodipicolinate reductaseNot AvailableEscherichia coli (strain K12)
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
131704240
PubChem Substance
46506585
ChemSpider
110455
HET
A3D
PDB Entries
1drv / 1pzf / 1pzg / 4nd2

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 Solubility2.12 mg/mLALOGPS
logP-0.89ALOGPS
logP-9.9ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area295.07 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity142.2 m3·mol-1ChemAxon
Polarizability58.98 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8925
Blood Brain Barrier+0.7154
Caco-2 permeable-0.7333
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8837
P-glycoprotein inhibitor IINon-inhibitor0.9556
Renal organic cation transporterNon-inhibitor0.9423
CYP450 2C9 substrateNon-substrate0.8098
CYP450 2D6 substrateNon-substrate0.8372
CYP450 3A4 substrateSubstrate0.5196
CYP450 1A2 substrateNon-inhibitor0.9056
CYP450 2C9 inhibitorNon-inhibitor0.9104
CYP450 2D6 inhibitorNon-inhibitor0.9023
CYP450 2C19 inhibitorNon-inhibitor0.9003
CYP450 3A4 inhibitorNon-inhibitor0.8794
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9065
Ames testNon AMES toxic0.8324
CarcinogenicityNon-carcinogens0.8995
BiodegradationNot ready biodegradable0.9804
Rat acute toxicity2.6894 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9615
hERG inhibition (predictor II)Non-inhibitor0.6287
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

Classification
Not classified

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on ch or ch2 groups, nad or nadp as acceptor
Specific Function
Catalyzes the conversion of 4-hydroxy-tetrahydrodipicolinate (HTPA) to tetrahydrodipicolinate. Can use both NADH and NADPH as a reductant, with NADH being twice as effective as NADPH.
Gene Name
dapB
Uniprot ID
P04036
Uniprot Name
4-hydroxy-tetrahydrodipicolinate reductase
Molecular Weight
28756.34 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 05:49