NAV

[(3,7,11-TRIMETHYL-DODECA-2,6,10-TRIENYLOXYCARBAMOYL)-METHYL]-PHOSPHONIC ACID

Identification

Generic Name
[(3,7,11-TRIMETHYL-DODECA-2,6,10-TRIENYLOXYCARBAMOYL)-METHYL]-PHOSPHONIC ACID
DrugBank Accession Number
DB07771
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 359.3976
Monoisotopic: 359.186159587
Chemical Formula
C17H30NO5P
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
UGTPase KRasNot AvailableHumans
UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaNot AvailableHumans
UProtein farnesyltransferase subunit betaNot 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 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 / Carboxylic acids and derivatives / Organopnictogen compounds / Organophosphorus compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid derivative / Farsesane sesquiterpenoid / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen 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
JAOBYUCYSAOLHS-XGGJEREUSA-N
InChI
InChI=1S/C17H30NO5P/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-23-18-17(19)13-24(20,21)22/h7,9,11H,5-6,8,10,12-13H2,1-4H3,(H,18,19)(H2,20,21,22)/b15-9+,16-11+
IUPAC Name
[({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy}carbamoyl)methyl]phosphonic acid
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CONC(=O)CP(O)(O)=O

References

General References
Not Available
PubChem Compound
445015
PubChem Substance
99444242
ChemSpider
392777
ZINC
ZINC000002046984
PDBe Ligand
FII
PDB Entries
1d8d / 1d8e / 1jcs / 1tn6 / 1tn7 / 1tn8 / 2iej / 3q75 / 3sfx / 3sfy …
show 2 more

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 Solubility0.0044 mg/mLALOGPS
logP2.79ALOGPS
logP2.61Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)1.66Chemaxon
pKa (Strongest Basic)-4.6Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area95.86 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity98.43 m3·mol-1Chemaxon
Polarizability39.39 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5284
Blood Brain Barrier+0.7356
Caco-2 permeable-0.6183
P-glycoprotein substrateSubstrate0.5447
P-glycoprotein inhibitor INon-inhibitor0.5675
P-glycoprotein inhibitor IINon-inhibitor0.547
Renal organic cation transporterNon-inhibitor0.9435
CYP450 2C9 substrateNon-substrate0.8158
CYP450 2D6 substrateNon-substrate0.8084
CYP450 3A4 substrateSubstrate0.5387
CYP450 1A2 substrateNon-inhibitor0.7437
CYP450 2C9 inhibitorNon-inhibitor0.761
CYP450 2D6 inhibitorNon-inhibitor0.8729
CYP450 2C19 inhibitorNon-inhibitor0.6844
CYP450 3A4 inhibitorNon-inhibitor0.8292
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9413
Ames testNon AMES toxic0.5493
CarcinogenicityNon-carcinogens0.6639
BiodegradationNot ready biodegradable0.5596
Rat acute toxicity2.5856 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9482
hERG inhibition (predictor II)Non-inhibitor0.8457
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-MSsplash10-00du-3921000000-0783be47fdd2905c5829
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1559000000-0d77b2d7c787f00459bc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-2de391de92874827e2ee
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9112000000-3d303854613a56748fb6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fl1-2922000000-854dba6a31bf78f26ad2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0211-8930000000-e17611d4af25d6a56a2f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9510000000-05770a9e8ec853726c8d
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]-181.7354
predicted
DeepCCS 1.0 (2019)
[M+H]+184.0934
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.86812
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. GTPase KRas
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein complex binding
Specific Function
Ras proteins bind GDP/GTP and possess intrinsic GTPase activity. Plays an important role in the regulation of cell proliferation (PubMed:23698361, PubMed:22711838).
Gene Name
KRAS
Uniprot ID
P01116
Uniprot Name
GTPase KRas
Molecular Weight
21655.67 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]
Details3. 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]

Drug created at September 15, 2010 21:25 / Updated at June 12, 2020 16:52