Adenylosuccinic Acid

Identification

Name
Adenylosuccinic Acid
Accession Number
DB04418  (EXPT00146)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Aspartyl adenylate
  • N-[9-(5-O-phosphono-beta-D-ribofuranosyl)-9H-purin-6-yl]aspartic acid
  • N(6)-(1,2-dicarboxyethyl)-AMP
  • N(6)-(1,2-dicarboxyethyl)AMP
Categories
UNII
X1B4ZJ0IIV
CAS number
19046-78-7
Weight
Average: 463.2934
Monoisotopic: 463.074042955
Chemical Formula
C14H18N5O11P
InChI Key
OFBHPPMPBOJXRT-VWJPMABRSA-N
InChI
InChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5-,6+,9+,10+,13+/m0/s1
IUPAC Name
(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C(N[C@@H](CC(O)=O)C(O)=O)N=CN=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAdenylosuccinate synthetase isozyme 1Not 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
PathwayCategory
Purine Nucleotides De Novo Biosynthesis 2Metabolic
Purine Nucleotides De Novo BiosynthesisMetabolic
Purine Nucleotides De Novo Biosynthesis Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0059653
KEGG Compound
C03794
PubChem Compound
447145
PubChem Substance
46509168
ChemSpider
394323
ChEBI
15919
HET
2SA
PDB Entries
1mez / 2ptr / 2vd6 / 5nx9

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 Solubility2.38 mg/mLALOGPS
logP-2ALOGPS
logP-5.3ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.58ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area246.68 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity96.18 m3·mol-1ChemAxon
Polarizability39.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9115
Blood Brain Barrier+0.5525
Caco-2 permeable-0.7522
P-glycoprotein substrateNon-substrate0.565
P-glycoprotein inhibitor INon-inhibitor0.8586
P-glycoprotein inhibitor IINon-inhibitor0.9604
Renal organic cation transporterNon-inhibitor0.9599
CYP450 2C9 substrateNon-substrate0.7785
CYP450 2D6 substrateNon-substrate0.8399
CYP450 3A4 substrateNon-substrate0.5111
CYP450 1A2 substrateNon-inhibitor0.8553
CYP450 2C9 inhibitorNon-inhibitor0.9289
CYP450 2D6 inhibitorNon-inhibitor0.8592
CYP450 2C19 inhibitorNon-inhibitor0.9324
CYP450 3A4 inhibitorNon-inhibitor0.9103
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9492
Ames testNon AMES toxic0.8687
CarcinogenicityNon-carcinogens0.9143
BiodegradationNot ready biodegradable0.7855
Rat acute toxicity2.6431 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9813
hERG inhibition (predictor II)Non-inhibitor0.834
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f8a-0091600000-d3ff612cea73450d5c19
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-0290000000-e7e3d8c35b40ea40e3b8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1390000000-f734f11568b018669694
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0imj-5080900000-59f4f4d8892f9c1e81f1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fb9-9180100000-ae2ec357f2c79556d583
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9010000000-e788111b4885f014689f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0000900000-682db2581239b5c0a595
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0000900000-ab92d302fce66b902faa
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-01ot-7143900000-e73b0c364a41781e7287
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9420000000-b8052106219be7dd584e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-005a-9500000000-83812f91a1e7849cdf9c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0090000000-46a1360de4b17c75e2e0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9550000000-e31a634109a93503ef6e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0059-9700000000-976efe169398b143430f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0059-9600000000-da7d432450879199d87a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9300000000-432a2295a3e2d9e5e196
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0000900000-3303cf34d7c785b2bd2e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0w29-0080900000-ed11d2f1a5b98f01a24b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0090000000-e04eacd49705ed3253bd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0290000000-8e84bc7ec6914f71a462
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ikl-1940000000-d1f576d2848684937eb3
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0udi-0190000000-4db35b93ee46253bf027

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Aspartic acid and derivatives / Glycosylamines / 6-alkylaminopurines / L-alpha-amino acids / Monosaccharide phosphates / Aminopyrimidines and derivatives / Secondary alkylarylamines / Monoalkyl phosphates / Imidolactams
show 14 more
Substituents
Purine ribonucleoside monophosphate / Pentose-5-phosphate / Pentose phosphate / Aspartic acid or derivatives / N-glycosyl compound / 6-alkylaminopurine / Glycosyl compound / L-alpha-amino acid / Monosaccharide phosphate / Alpha-amino acid or derivatives
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phosphate ion binding
Specific Function
Component of the purine nucleotide cycle (PNC), which interconverts IMP and AMP to regulate the nucleotide levels in various tissues, and which contributes to glycolysis and ammoniagenesis. Catalyz...
Gene Name
ADSSL1
Uniprot ID
Q8N142
Uniprot Name
Adenylosuccinate synthetase isozyme 1
Molecular Weight
50208.16 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 05:56