NAV

ALPHA-HYDROXYFARNESYLPHOSPHONIC ACID

Identification

Generic Name
ALPHA-HYDROXYFARNESYLPHOSPHONIC ACID
DrugBank Accession Number
DB07895
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 308.3939
Monoisotopic: 308.211646056
Chemical Formula
C15H33O4P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProtein farnesyltransferase subunit betaNot AvailableHumans
UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaNot 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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Sesquiterpenoids
Direct Parent
Sesquiterpenoids
Alternative Parents
Organic phosphonic acids / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Farsesane sesquiterpenoid / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organooxygen compound / Organophosphonic acid / Organophosphonic acid derivative / Organophosphorus compound / Organopnictogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IJNCEETVCWDDQB-KFWWJZLASA-N
InChI
InChI=1S/C15H33O4P/c1-12(2)7-5-8-13(3)9-6-10-14(4)11-15(16)20(17,18)19/h12-16H,5-11H2,1-4H3,(H2,17,18,19)/t13-,14-,15+/m1/s1
IUPAC Name
[(1S,3R,7R)-1-hydroxy-3,7,11-trimethyldodecyl]phosphonic acid
SMILES
[H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)C[C@@]([H])(O)P(O)(O)=O

References

General References
Not Available
PubChem Compound
46937103
PubChem Substance
99444366
ChemSpider
25057560
ZINC
ZINC000006762173
PDBe Ligand
HFP
PDB Entries
1n94 / 1n95 / 1n9a / 1ni1 / 1nl4 / 1qbq

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 Solubility0.109 mg/mLALOGPS
logP3.35ALOGPS
logP3.8Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)1.3Chemaxon
pKa (Strongest Basic)-3.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area77.76 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity83.11 m3·mol-1Chemaxon
Polarizability35.61 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7897
Blood Brain Barrier+0.8279
Caco-2 permeable-0.5925
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9329
P-glycoprotein inhibitor IINon-inhibitor0.9647
Renal organic cation transporterNon-inhibitor0.9649
CYP450 2C9 substrateNon-substrate0.7719
CYP450 2D6 substrateNon-substrate0.8106
CYP450 3A4 substrateNon-substrate0.5069
CYP450 1A2 substrateNon-inhibitor0.8413
CYP450 2C9 inhibitorNon-inhibitor0.8458
CYP450 2D6 inhibitorNon-inhibitor0.9185
CYP450 2C19 inhibitorNon-inhibitor0.8295
CYP450 3A4 inhibitorNon-inhibitor0.8766
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9755
Ames testNon AMES toxic0.784
CarcinogenicityNon-carcinogens0.6359
BiodegradationNot ready biodegradable0.8851
Rat acute toxicity1.6978 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9194
hERG inhibition (predictor II)Non-inhibitor0.7984
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-MSsplash10-001l-9740000000-575fb371ab5a0f572d2a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3396000000-256137b20402c7d10d2d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03e9-9000000000-09ed89999c64822c292c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-00d737b6384dfe047edf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0abl-9410000000-23c776ce8a58e750f870
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-e96b7302234f93441275
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-b3b13b08f89ebeb8ed43
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]-173.74455
predicted
DeepCCS 1.0 (2019)
[M+H]+176.59248
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.23848
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Protein farnesyltransferase subunit beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Essential subunit of the farnesyltransferase complex. Catalyzes the transfer of a farnesyl moiety from farnesyl diphosphate to a cysteine at the fourth position from the C-terminus of several prote...
Gene Name
FNTB
Uniprot ID
P49356
Uniprot Name
Protein farnesyltransferase subunit beta
Molecular Weight
48773.2 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]
Details2. Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Rab geranylgeranyltransferase activity
Specific Function
Essential subunit of both the farnesyltransferase and the geranylgeranyltransferase complex. Contributes to the transfer of a farnesyl or geranylgeranyl moiety from farnesyl or geranylgeranyl dipho...
Gene Name
FNTA
Uniprot ID
P49354
Uniprot Name
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Molecular Weight
44408.32 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 September 15, 2010 21:26 / Updated at June 12, 2020 16:52