NAV

Carbaphosphonate

Identification

Generic Name
Carbaphosphonate
DrugBank Accession Number
DB02592
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 270.1737
Monoisotopic: 270.050453968
Chemical Formula
C8H15O8P
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
U3-dehydroquinate synthaseNot AvailableStaphylococcus aureus (strain MRSA252)
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 quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Quinic acids and derivatives
Alternative Parents
Cyclohexanols / Alpha hydroxy acids and derivatives / Tertiary alcohols / Organic phosphonic acids / Polyols / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organophosphorus compounds / Organic oxides
show 2 more
Substituents
Aliphatic homomonocyclic compound / Alpha-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclohexanol / Hydrocarbon derivative / Hydroxy acid / Monocarboxylic acid or derivatives / Organic oxide
show 8 more
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BKLICLLAHMTUPK-UNGCPHIMSA-N
InChI
InChI=1S/C8H15O8P/c9-5-2-8(13,7(11)12)1-4(6(5)10)3-17(14,15)16/h4-6,9-10,13H,1-3H2,(H,11,12)(H2,14,15,16)/t4-,5-,6-,8+/m1/s1
IUPAC Name
(1S,3R,4R,5S)-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid
SMILES
[H][C@@]1(O)C[C@@](O)(C[C@]([H])(CP(O)(O)=O)[C@@]1([H])O)C(O)=O

References

General References
Not Available
PubChem Compound
445131
PubChem Substance
46505074
ChemSpider
392863
PDBe Ligand
CRB
PDB Entries
1dqs / 1nr5 / 1nvb / 1nvd / 1nvf / 1xag / 1xai / 1xaj / 1xal

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 Solubility42.1 mg/mLALOGPS
logP-2.7ALOGPS
logP-3.4Chemaxon
logS-0.81ALOGPS
pKa (Strongest Acidic)1.8Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area155.52 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity53.73 m3·mol-1Chemaxon
Polarizability23.01 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8732
Blood Brain Barrier+0.784
Caco-2 permeable-0.7376
P-glycoprotein substrateNon-substrate0.6546
P-glycoprotein inhibitor INon-inhibitor0.9171
P-glycoprotein inhibitor IINon-inhibitor0.9954
Renal organic cation transporterNon-inhibitor0.9328
CYP450 2C9 substrateNon-substrate0.818
CYP450 2D6 substrateNon-substrate0.8433
CYP450 3A4 substrateNon-substrate0.5671
CYP450 1A2 substrateNon-inhibitor0.9171
CYP450 2C9 inhibitorNon-inhibitor0.9234
CYP450 2D6 inhibitorNon-inhibitor0.9299
CYP450 2C19 inhibitorNon-inhibitor0.9189
CYP450 3A4 inhibitorNon-inhibitor0.961
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9968
Ames testNon AMES toxic0.797
CarcinogenicityNon-carcinogens0.8782
BiodegradationNot ready biodegradable0.7035
Rat acute toxicity2.1438 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9253
hERG inhibition (predictor II)Non-inhibitor0.9252
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-MSsplash10-0udi-2940000000-506fb1923d812fbff0b5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0190000000-03bec5e96edc0de43576
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-2769ba008656c81cdfa7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kg9-0290000000-e0fb47013f6a8aa72da6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gb9-0190000000-8d2e859b36d5ba2d18ba
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fkc-5910000000-02fee863d6915ece8e66
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-9220000000-f2ddafb4f73425c67834
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]-151.83122
predicted
DeepCCS 1.0 (2019)
[M+H]+154.22678
predicted
DeepCCS 1.0 (2019)
[M+Na]+160.75447
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-dehydroquinate synthase
Kind
Protein
Organism
Staphylococcus aureus (strain MRSA252)
Pharmacological action
Unknown
General Function
3-dehydroquinate synthase activity
Specific Function
Not Available
Gene Name
aroB
Uniprot ID
Q6GGU4
Uniprot Name
3-dehydroquinate synthase
Molecular Weight
40284.695 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 August 01, 2020 13:44