1,4-Dideoxy-5-Dehydro-O2-Sulfo-Glucuronic Acid

Identification

Name
1,4-Dideoxy-5-Dehydro-O2-Sulfo-Glucuronic Acid
Accession Number
DB03981  (EXPT03166)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 256.187
Monoisotopic: 255.988902544
Chemical Formula
C6H8O9S
InChI Key
VJIMUKBSNUBECH-YKKSOZKNSA-N
InChI
InChI=1S/C6H8O9S/c7-2-1-3(5(8)9)14-6(10)4(2)15-16(11,12)13/h1-2,4,6-7,10H,(H,8,9)(H,11,12,13)/t2-,4+,6+/m0/s1
IUPAC Name
(2R,3R,4S)-2,4-dihydroxy-3-(sulfooxy)-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES
[H][[email protected]@]1(O)OC(=C[[email protected]]([H])(O)[[email protected]@]1([H])OS(O)(=O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFibroblast growth factor 2Not AvailableHuman
UHeparan sulfate glucosamine 3-O-sulfotransferase 3A1Not AvailableHuman
UAnnexin A5Not 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
PubChem Compound
444552
PubChem Substance
46508196
ChemSpider
392452
HET
UAP
PDB Entries
1bfb / 1bfc / 1fq9 / 1g5n / 1t8u / 2hyu / 2hyv / 3ojv / 4pxq / 4rda
show 2 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 Solubility35.2 mg/mLALOGPS
logP-1.7ALOGPS
logP-3.9ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.59 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.14 m3·mol-1ChemAxon
Polarizability20.22 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5937
Blood Brain Barrier+0.8633
Caco-2 permeable-0.6346
P-glycoprotein substrateNon-substrate0.7339
P-glycoprotein inhibitor IInhibitor0.5155
P-glycoprotein inhibitor IINon-inhibitor0.9892
Renal organic cation transporterNon-inhibitor0.8978
CYP450 2C9 substrateNon-substrate0.8861
CYP450 2D6 substrateNon-substrate0.8294
CYP450 3A4 substrateNon-substrate0.5864
CYP450 1A2 substrateNon-inhibitor0.7895
CYP450 2C9 inhibitorNon-inhibitor0.8179
CYP450 2D6 inhibitorNon-inhibitor0.8883
CYP450 2C19 inhibitorNon-inhibitor0.7951
CYP450 3A4 inhibitorNon-inhibitor0.9895
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.963
Ames testNon AMES toxic0.5403
CarcinogenicityNon-carcinogens0.6387
BiodegradationReady biodegradable0.6335
Rat acute toxicity2.3128 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8954
hERG inhibition (predictor II)Non-inhibitor0.8606
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/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

Description
This compound belongs to the class of organic compounds known as sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic sulfuric acids and derivatives
Sub Class
Sulfuric acid esters
Direct Parent
Sulfuric acid monoesters
Alternative Parents
Alkyl sulfates / Secondary alcohols / Hemiacetals / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Sulfuric acid monoester / Sulfate-ester / Alkyl sulfate / Hemiacetal / Secondary alcohol / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Oxacycle / Organoheterocyclic compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ligand-dependent nuclear receptor transcription coactivator activity
Specific Function
Plays an important role in the regulation of cell survival, cell division, angiogenesis, cell differentiation and cell migration. Functions as potent mitogen in vitro.
Gene Name
FGF2
Uniprot ID
P09038
Uniprot Name
Fibroblast growth factor 2
Molecular Weight
30769.715 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
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan ...
Gene Name
HS3ST3A1
Uniprot ID
Q9Y663
Uniprot Name
Heparan sulfate glucosamine 3-O-sulfotransferase 3A1
Molecular Weight
44899.155 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
Phospholipid binding
Specific Function
This protein is an anticoagulant protein that acts as an indirect inhibitor of the thromboplastin-specific complex, which is involved in the blood coagulation cascade.
Gene Name
ANXA5
Uniprot ID
P08758
Uniprot Name
Annexin A5
Molecular Weight
35936.375 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 December 01, 2017 15:21