NAV

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

Identification

Generic Name
1,4-Dideoxy-5-Dehydro-O2-Sulfo-Glucuronic Acid
DrugBank Accession Number
DB03981
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 256.187
Monoisotopic: 255.988902544
Chemical Formula
C6H8O9S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UFibroblast growth factor 2Not AvailableHumans
UHeparan sulfate glucosamine 3-O-sulfotransferase 3A1Not AvailableHumans
UAnnexin A5Not AvailableHumans
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

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 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
Alcohol / Aliphatic heteromonocyclic compound / Alkyl sulfate / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hemiacetal / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@@]1(O)OC(=C[C@]([H])(O)[C@@]1([H])OS(O)(=O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
444552
PubChem Substance
46508196
ChemSpider
392452
ZINC
ZINC000005834516
PDBe Ligand
UAP
PDB Entries
1bfb / 1bfc / 1fq9 / 1g5n / 1t8u / 1u4l / 1u4m / 2fut / 2hyu / 2hyv …
show 8 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-4Chemaxon
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-MSsplash10-0f76-9840000000-3a28f80a93f69bcc9eec
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0090000000-f495c7fe041ff88e12e0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-fcbb32c7b4998a52be21
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06di-3900000000-f53453cc853efe805222
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9710000000-3d84330dbffb44d3d78d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9200000000-ac22c6498517084bcc47
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9100000000-dbca28f029673861de8c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-145.96758
predicted
DeepCCS 1.0 (2019)
[M+H]+148.36339
predicted
DeepCCS 1.0 (2019)
[M+Na]+154.37668
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Fibroblast growth factor 2
Kind
Protein
Organism
Humans
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. [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. Heparan sulfate glucosamine 3-O-sulfotransferase 3A1
Kind
Protein
Organism
Humans
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. [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]
Details3. Annexin A5
Kind
Protein
Organism
Humans
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. [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]
  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. [Article]

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