NAV

(1R,2R,3S,4R,6S)-3,4,6-Trihydroxy-5-{[(S)-hydroxy(3-hydroxy-2-oxopropoxy)phosphoryl]oxy}-1,2-cyclohexanediyl bis[dihydrogen (phosphate)]

Identification

Generic Name
(1R,2R,3S,4R,6S)-3,4,6-Trihydroxy-5-{[(S)-hydroxy(3-hydroxy-2-oxopropoxy)phosphoryl]oxy}-1,2-cyclohexanediyl bis[dihydrogen (phosphate)]
DrugBank Accession Number
DB02028
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 492.1582
Monoisotopic: 491.983508718
Chemical Formula
C9H19O17P3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTubby protein homologNot 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 inositol phosphates. These are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Inositol phosphates
Alternative Parents
Monosaccharide phosphates / Monoalkyl phosphates / Dialkyl phosphates / Cyclohexanols / Glycerone and derivatives / Alpha-hydroxy ketones / Polyols / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Aliphatic homomonocyclic compound / Alkyl phosphate / Alpha-hydroxy ketone / Carbonyl group / Cyclohexanol / Dialkyl phosphate / Glycerone or derivatives / Hydrocarbon derivative / Inositol phosphate / Ketone
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
JBQPYAMQMBKZDT-WKBARDANSA-N
InChI
InChI=1S/C9H19O17P3/c10-1-3(11)2-23-29(21,22)26-7-4(12)5(13)8(24-27(15,16)17)9(6(7)14)25-28(18,19)20/h4-10,12-14H,1-2H2,(H,21,22)(H2,15,16,17)(H2,18,19,20)/t4-,5+,6+,7?,8-,9-/m1/s1
IUPAC Name
{[(1R,2S,3R,5S,6R)-2,3,5-trihydroxy-4-{[hydroxy(3-hydroxy-2-oxopropoxy)phosphoryl]oxy}-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid
SMILES
OCC(=O)COP(O)(=O)OC1[C@H](O)[C@H](O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H]1O

References

General References
Not Available
PubChem Compound
5288599
PubChem Substance
46505118
ChemSpider
4450728
PDBe Ligand
IBS
PDB Entries
1i7e

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 Solubility14.3 mg/mLALOGPS
logP-0.82ALOGPS
logP-4.8Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)0.62Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-5Chemaxon
Hydrogen Acceptor Count13Chemaxon
Hydrogen Donor Count9Chemaxon
Polar Surface Area287.27 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity84.21 m3·mol-1Chemaxon
Polarizability36.19 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8424
Blood Brain Barrier+0.7364
Caco-2 permeable-0.7198
P-glycoprotein substrateNon-substrate0.6836
P-glycoprotein inhibitor INon-inhibitor0.7143
P-glycoprotein inhibitor IINon-inhibitor0.969
Renal organic cation transporterNon-inhibitor0.9072
CYP450 2C9 substrateNon-substrate0.8346
CYP450 2D6 substrateNon-substrate0.8418
CYP450 3A4 substrateNon-substrate0.6302
CYP450 1A2 substrateNon-inhibitor0.891
CYP450 2C9 inhibitorNon-inhibitor0.91
CYP450 2D6 inhibitorNon-inhibitor0.9253
CYP450 2C19 inhibitorNon-inhibitor0.9017
CYP450 3A4 inhibitorNon-inhibitor0.9661
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9849
Ames testNon AMES toxic0.8089
CarcinogenicityNon-carcinogens0.8178
BiodegradationNot ready biodegradable0.5817
Rat acute toxicity2.0261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8977
hERG inhibition (predictor II)Non-inhibitor0.8792
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0400900000-982effb998153e69e121
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0000900000-df5d3936839b1d0c4e03
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2007900000-049dc12935eef1e18fc7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000200000-478ef462d58d6fe9b638
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-d771b8c8c4781d6f87d2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9214100000-15d0aad40030e28b0a59
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]-172.32736
predicted
DeepCCS 1.0 (2019)
[M+H]+174.33617
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.2487
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Tubby protein homolog
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein complex binding
Specific Function
Functions in signal transduction from heterotrimeric G protein-coupled receptors. Binds to membranes containing phosphatidylinositol 4,5-bisphosphate. Can bind DNA (in vitro). May contribute to the...
Gene Name
TUB
Uniprot ID
P50607
Uniprot Name
Tubby protein homolog
Molecular Weight
55650.695 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. [Article]

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