Identification

Generic Name
3-deoxy-alpha-D-manno-oct-2-ulopyranosonic acid
DrugBank Accession Number
DB03548
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 238.192
Monoisotopic: 238.068867424
Chemical Formula
C8H14O8
Synonyms
  • 3-deoxy-α-D-manno-oct-2-ulopyranosonic acid
  • α-2-keto-3-deoxyoctulosonic acid pyranose
  • α-Kdo
  • α-KDop

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UFerrichrome-iron receptorNot 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

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 c-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a C-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
C-glucuronides
Alternative Parents
C-glycosyl compounds / Pyrans / Oxanes / Monosaccharides / Alpha hydroxy acids and derivatives / Secondary alcohols / Hemiacetals / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives
show 5 more
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Alpha-hydroxy acid / C-glucuronide / C-glycosyl compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Glycosyl compound / Hemiacetal
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
3-deoxy-D-manno-octulosonic acid (CHEBI:43577)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NNLZBVFSCVTSLA-HXUQBWEZSA-N
InChI
InChI=1S/C8H14O8/c9-2-4(11)6-5(12)3(10)1-8(15,16-6)7(13)14/h3-6,9-12,15H,1-2H2,(H,13,14)/t3-,4-,5-,6-,8-/m1/s1
IUPAC Name
(2R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-2,4,5-trihydroxyoxane-2-carboxylic acid
SMILES
[H][C@@]1(O[C@](O)(C[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)CO

References

General References
Not Available
PubChem Compound
445569
PubChem Substance
46506707
ChemSpider
393174
ChEBI
43577
ZINC
ZINC000005851513
PDBe Ligand
KDO
PDB Entries
1fcp / 1fi1 / 1q9w / 1qff / 1qfg / 1qjq / 1qkc / 2fcp / 2grx / 2r1y
show 50 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 Solubility612.0 mg/mLALOGPS
logP-2.8ALOGPS
logP-2.6ChemAxon
logS0.41ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area147.68 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.72 m3·mol-1ChemAxon
Polarizability21.11 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.771
Blood Brain Barrier+0.5515
Caco-2 permeable-0.8771
P-glycoprotein substrateNon-substrate0.5631
P-glycoprotein inhibitor INon-inhibitor0.9459
P-glycoprotein inhibitor IINon-inhibitor0.9702
Renal organic cation transporterNon-inhibitor0.919
CYP450 2C9 substrateNon-substrate0.8403
CYP450 2D6 substrateNon-substrate0.886
CYP450 3A4 substrateNon-substrate0.6572
CYP450 1A2 substrateNon-inhibitor0.9832
CYP450 2C9 inhibitorNon-inhibitor0.9781
CYP450 2D6 inhibitorNon-inhibitor0.966
CYP450 2C19 inhibitorNon-inhibitor0.9764
CYP450 3A4 inhibitorNon-inhibitor0.9603
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.991
Ames testNon AMES toxic0.8122
CarcinogenicityNon-carcinogens0.9612
BiodegradationReady biodegradable0.8952
Rat acute toxicity1.2271 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9919
hERG inhibition (predictor II)Non-inhibitor0.9392
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

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Virion binding
Specific Function
This receptor binds the ferrichrome-iron ligand. It interacts with the TonB protein, which is responsible for energy coupling of the ferrichrome-promoted iron transport system. Acts as a receptor f...
Gene Name
fhuA
Uniprot ID
P06971
Uniprot Name
Ferrichrome-iron receptor
Molecular Weight
82181.75 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]

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