You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name7-[3-(4-FLUORO-PHENYL)-1-ISOPROPYL-1H-INDOL-2-YL]-3,5-DIHYDROXY-HEPTANOIC ACID
Accession NumberDB06846
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 413.4818
Monoisotopic: 413.200236594
Chemical FormulaC24H28FNO4
InChI KeyInChIKey=MVPCJBDHTUCOBT-RTBURBONSA-N
InChI
InChI=1S/C24H28FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-10,15,18-19,27-28H,11-14H2,1-2H3,(H,29,30)/t18-,19-/m1/s1
IUPAC Name
(3R,5R)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyheptanoic acid
SMILES
[H][C@@](O)(CCC1=C(C2=C(C=CC=C2)N1C(C)C)C1=CC=C(F)C=C1)C[C@@]([H])(O)CC(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 3-phenylpyrrole
  • Medium-chain hydroxy acid
  • Indole or derivatives
  • Indole
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Halogenated fatty acid
  • Halobenzene
  • Fluorobenzene
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9896
Blood Brain Barrier+0.6927
Caco-2 permeable-0.5992
P-glycoprotein substrateSubstrate0.5882
P-glycoprotein inhibitor INon-inhibitor0.6162
P-glycoprotein inhibitor IINon-inhibitor0.5553
Renal organic cation transporterNon-inhibitor0.75
CYP450 2C9 substrateNon-substrate0.7962
CYP450 2D6 substrateNon-substrate0.5325
CYP450 3A4 substrateSubstrate0.6804
CYP450 1A2 substrateNon-inhibitor0.6863
CYP450 2C9 inhibitorNon-inhibitor0.7665
CYP450 2D6 inhibitorNon-inhibitor0.8755
CYP450 2C19 inhibitorNon-inhibitor0.7074
CYP450 3A4 inhibitorNon-inhibitor0.8601
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6139
Ames testNon AMES toxic0.8522
CarcinogenicityNon-carcinogens0.8845
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8762 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.968
hERG inhibition (predictor II)Non-inhibitor0.6464
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00691 mg/mLALOGPS
logP3.88ALOGPS
logP3.79ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.69 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity114.05 m3·mol-1ChemAxon
Polarizability44.66 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nadph binding
Specific Function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
Molecular Weight:
97475.155 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 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:17 / Updated on September 16, 2013 18:04