2-HYDROXYMETHYL-6-OCTYLSULFANYL-TETRAHYDRO-PYRAN-3,4,5-TRIOL

Identification

Name
2-HYDROXYMETHYL-6-OCTYLSULFANYL-TETRAHYDRO-PYRAN-3,4,5-TRIOL
Accession Number
DB08558
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: 308.434
Monoisotopic: 308.165744696
Chemical Formula
C14H28O5S
InChI Key
CGVLVOOFCGWBCS-RGDJUOJXSA-N
InChI
InChI=1S/C14H28O5S/c1-2-3-4-5-6-7-8-20-14-13(18)12(17)11(16)10(9-15)19-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14+/m1/s1
IUPAC Name
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(octylsulfanyl)oxane-3,4,5-triol
SMILES
[H][[email protected]]1(CO)O[[email protected]@]([H])(SCCCCCCCC)[[email protected]]([H])(O)[[email protected]@]([H])(O)[[email protected]]1([H])O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAcyl-[acyl-carrier-protein]--UDP-N-acetylglucosamine O-acyltransferaseNot AvailableHelicobacter pylori (strain ATCC 700392 / 26695)
UDiacylglycerol acyltransferase/mycolyltransferase Ag85CNot AvailableMycobacterium tuberculosis
UBeta-1 adrenergic receptorNot AvailableHuman
ULactase-phlorizin hydrolaseNot 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
656909
PubChem Substance
99445029
ChemSpider
571158
HET
SOG
PDB Entries
1j2z / 1va5 / 2vt4 / 2ycx / 2ycy / 2ycz / 2ydo / 2ydv / 2zzl / 3gnp
show 7 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 Solubility3.67 mg/mLALOGPS
logP1.85ALOGPS
logP1.42ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity79.12 m3·mol-1ChemAxon
Polarizability35.6 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5909
Blood Brain Barrier-0.5438
Caco-2 permeable-0.6631
P-glycoprotein substrateSubstrate0.6216
P-glycoprotein inhibitor INon-inhibitor0.8817
P-glycoprotein inhibitor IINon-inhibitor0.8834
Renal organic cation transporterNon-inhibitor0.8263
CYP450 2C9 substrateNon-substrate0.8071
CYP450 2D6 substrateNon-substrate0.8022
CYP450 3A4 substrateNon-substrate0.5645
CYP450 1A2 substrateNon-inhibitor0.8056
CYP450 2C9 inhibitorNon-inhibitor0.8152
CYP450 2D6 inhibitorNon-inhibitor0.8851
CYP450 2C19 inhibitorNon-inhibitor0.625
CYP450 3A4 inhibitorNon-inhibitor0.797
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8632
Ames testNon AMES toxic0.7807
CarcinogenicityNon-carcinogens0.9307
BiodegradationNot ready biodegradable0.6575
Rat acute toxicity1.8727 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9125
hERG inhibition (predictor II)Non-inhibitor0.6428
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 thioglycosides. These are glycoside in which a sugar group is bonded through one carbon to another group via a S-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Thioglycosides
Alternative Parents
Oxanes / Monosaccharides / Monothioacetals / Secondary alcohols / Sulfenyl compounds / Polyols / Oxacyclic compounds / Primary alcohols / Hydrocarbon derivatives
Substituents
S-glycosyl compound / Oxane / Monosaccharide / Monothioacetal / Secondary alcohol / Oxacycle / Organoheterocyclic compound / Sulfenyl compound / Polyol / Hydrocarbon derivative
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Helicobacter pylori (strain ATCC 700392 / 26695)
Pharmacological action
Unknown
General Function
Acyl-[acyl-carrier-protein]-udp-n-acetylglucosamine o-acyltransferase activity
Specific Function
Involved in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell.
Gene Name
lpxA
Uniprot ID
O25927
Uniprot Name
Acyl-[acyl-carrier-protein]--UDP-N-acetylglucosamine O-acyltransferase
Molecular Weight
29855.195 Da
References
  1. 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]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
The antigen 85 proteins (FbpA, FbpB, FbpC) are responsible for the high affinity of mycobacteria to fibronectin, a large adhesive glycoprotein, which facilitates the attachment of M.tuberculosis to murine alveolar macrophages (AMs). They also help to maintain the integrity of the cell wall by catalyzing the transfer of mycolic acids to cell wall arabinogalactan and through the synthesis of alpha,alpha-trehalose dimycolate (TDM, cord factor). They catalyze the transfer of a mycoloyl residue from one molecule of alpha,alpha-trehalose monomycolate (TMM) to another TMM, leading to the formation of TDM.
Specific Function
Diacylglycerol o-acyltransferase activity
Gene Name
fbpC
Uniprot ID
P9WQN9
Uniprot Name
Diacylglycerol acyltransferase/mycolyltransferase Ag85C
Molecular Weight
36771.025 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity
Specific Function
LPH splits lactose in the small intestine.
Gene Name
LCT
Uniprot ID
P09848
Uniprot Name
Lactase-phlorizin hydrolase
Molecular Weight
218584.77 Da
References
  1. 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 September 15, 2010 15:32 / Updated on December 01, 2017 16:06