1-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-4-METHYL-1H-INDOLE

Identification

Name
1-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-4-METHYL-1H-INDOLE
Accession Number
DB07116
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: 327.2696
Monoisotopic: 327.087173825
Chemical Formula
C14H18NO6P
InChI Key
UXXYPWCUINVUHL-BFHYXJOUSA-N
InChI
InChI=1S/C14H18NO6P/c1-9-3-2-4-11-10(9)5-6-15(11)14-7-12(16)13(21-14)8-20-22(17,18)19/h2-6,12-14,16H,7-8H2,1H3,(H2,17,18,19)/t12-,13+,14+/m0/s1
IUPAC Name
{[(2R,3S,5R)-3-hydroxy-5-(4-methyl-1H-indol-1-yl)oxolan-2-yl]methoxy}phosphonic acid
SMILES
[H][[email protected]]1(O)C[[email protected]@]([H])(O[[email protected]]1([H])COP(O)(O)=O)N1C=CC2=C(C)C=CC=C12

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUracil-DNA glycosylaseNot 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
46937051
PubChem Substance
99443587
ChemSpider
25057511
HET
4MF
PDB Entries
2oxm / 2oyt

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 Solubility1.15 mg/mLALOGPS
logP0.69ALOGPS
logP1.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.15 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.14 m3·mol-1ChemAxon
Polarizability31.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9444
Blood Brain Barrier+0.9281
Caco-2 permeable-0.6501
P-glycoprotein substrateNon-substrate0.7265
P-glycoprotein inhibitor INon-inhibitor0.7913
P-glycoprotein inhibitor IINon-inhibitor0.9468
Renal organic cation transporterNon-inhibitor0.9028
CYP450 2C9 substrateNon-substrate0.7617
CYP450 2D6 substrateNon-substrate0.7987
CYP450 3A4 substrateSubstrate0.6055
CYP450 1A2 substrateNon-inhibitor0.8128
CYP450 2C9 inhibitorNon-inhibitor0.8317
CYP450 2D6 inhibitorNon-inhibitor0.8971
CYP450 2C19 inhibitorNon-inhibitor0.7824
CYP450 3A4 inhibitorNon-inhibitor0.9414
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8103
Ames testNon AMES toxic0.6206
CarcinogenicityNon-carcinogens0.8354
BiodegradationNot ready biodegradable0.9358
Rat acute toxicity2.4263 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9354
hERG inhibition (predictor II)Non-inhibitor0.7603
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 n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
N-alkylindoles
Direct Parent
N-alkylindoles
Alternative Parents
Indoles / Monoalkyl phosphates / Substituted pyrroles / Benzenoids / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
N-alkylindole / Indole / Monoalkyl phosphate / Organic phosphoric acid derivative / Phosphoric acid ester / Substituted pyrrole / Alkyl phosphate / Benzenoid / Pyrrole / Tetrahydrofuran
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Uracil dna n-glycosylase activity
Specific Function
Excises uracil residues from the DNA which can arise as a result of misincorporation of dUMP residues by DNA polymerase or due to deamination of cytosine.
Gene Name
UNG
Uniprot ID
P13051
Uniprot Name
Uracil-DNA glycosylase
Molecular Weight
34645.27 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 15:19 / Updated on December 01, 2017 15:46