(1R)-menthyl hexyl phosphonate group

Identification

Name
(1R)-menthyl hexyl phosphonate group
Accession Number
DB08200
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: 304.4052
Monoisotopic: 304.216731434
Chemical Formula
C16H33O3P
InChI Key
WAVIZOVSJOXCKT-OWCLPIDISA-N
InChI
InChI=1S/C16H33O3P/c1-5-6-7-8-11-20(17,18)19-16-12-14(4)9-10-15(16)13(2)3/h13-16H,5-12H2,1-4H3,(H,17,18)/t14-,15+,16-/m1/s1
IUPAC Name
hexyl({[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy})phosphinic acid
SMILES
CCCCCCP(O)(=O)O[[email protected]@H]1C[[email protected]](C)CC[[email protected]]1C(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCholinesteraseNot 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
446980
PubChem Substance
99444671
ChemSpider
394197
HET
MPA
PDB Entries
1lpm

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 Solubility0.0384 mg/mLALOGPS
logP4.34ALOGPS
logP4.58ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)1.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.04 m3·mol-1ChemAxon
Polarizability35.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9841
Blood Brain Barrier+0.9329
Caco-2 permeable+0.5468
P-glycoprotein substrateNon-substrate0.5429
P-glycoprotein inhibitor INon-inhibitor0.5578
P-glycoprotein inhibitor IINon-inhibitor0.9095
Renal organic cation transporterNon-inhibitor0.9001
CYP450 2C9 substrateNon-substrate0.8084
CYP450 2D6 substrateNon-substrate0.7953
CYP450 3A4 substrateSubstrate0.6334
CYP450 1A2 substrateNon-inhibitor0.8461
CYP450 2C9 inhibitorNon-inhibitor0.7973
CYP450 2D6 inhibitorNon-inhibitor0.8921
CYP450 2C19 inhibitorNon-inhibitor0.8028
CYP450 3A4 inhibitorNon-inhibitor0.6856
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9095
Ames testNon AMES toxic0.6676
CarcinogenicityNon-carcinogens0.6701
BiodegradationNot ready biodegradable0.9493
Rat acute toxicity1.9734 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6445
hERG inhibition (predictor II)Non-inhibitor0.6372
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 menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Menthane monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Phosphonic acid esters / Organic phosphonic acids / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
P-menthane monoterpenoid / Monocyclic monoterpenoid / Phosphonic acid ester / Organophosphonic acid derivative / Organophosphonic acid / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organophosphorus compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 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 15:29 / Updated on December 01, 2017 16:01