3-Fluoro-4-{[(2R)-2-hydroxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)acetyl]amino}benzoic acid

Identification

Name
3-Fluoro-4-{[(2R)-2-hydroxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)acetyl]amino}benzoic acid
Accession Number
DB07031
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
BMS 270394 / BMS 961 / BMS-270394 / BMS270394
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 399.4552
Monoisotopic: 399.18458653
Chemical Formula
C23H26FNO4
InChI Key
AANFHDFOMFRLLR-LJQANCHMSA-N
InChI
InChI=1S/C23H26FNO4/c1-22(2)9-10-23(3,4)16-11-13(5-7-15(16)22)19(26)20(27)25-18-8-6-14(21(28)29)12-17(18)24/h5-8,11-12,19,26H,9-10H2,1-4H3,(H,25,27)(H,28,29)/t19-/m1/s1
IUPAC Name
3-fluoro-4-[(2R)-2-hydroxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetamido]benzoic acid
SMILES
CC1(C)CCC(C)(C)C2=C1C=CC(=C2)[[email protected]@H](O)C(=O)NC1=C(F)C=C(C=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
URetinoic acid receptor gammaNot 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
445455
PubChem Substance
99443502
ChemSpider
393092
BindingDB
31889
IUPHAR
2653
Guide to Pharmacology
GtP Drug Page
HET
394
PDB Entries
1exa

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 Solubility0.00116 mg/mLALOGPS
logP4.55ALOGPS
logP4.76ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.98 m3·mol-1ChemAxon
Polarizability42.49 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8827
Blood Brain Barrier+0.8198
Caco-2 permeable-0.5564
P-glycoprotein substrateSubstrate0.5738
P-glycoprotein inhibitor INon-inhibitor0.6914
P-glycoprotein inhibitor IINon-inhibitor0.7239
Renal organic cation transporterNon-inhibitor0.9661
CYP450 2C9 substrateNon-substrate0.7784
CYP450 2D6 substrateNon-substrate0.8425
CYP450 3A4 substrateSubstrate0.6637
CYP450 1A2 substrateNon-inhibitor0.5861
CYP450 2C9 inhibitorNon-inhibitor0.6488
CYP450 2D6 inhibitorNon-inhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.6047
CYP450 3A4 inhibitorNon-inhibitor0.9184
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6563
Ames testNon AMES toxic0.8222
CarcinogenicityNon-carcinogens0.7808
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2939 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9984
hERG inhibition (predictor II)Non-inhibitor0.8129
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 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 acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Acylaminobenzoic acid and derivatives
Alternative Parents
Tetralins / 3-halobenzoic acids / Halobenzoic acids / Anilides / Benzoic acids / N-arylamides / Benzoyl derivatives / Fluorobenzenes / Aryl fluorides / Secondary alcohols
show 9 more
Substituents
Acylaminobenzoic acid or derivatives / Tetralin / 3-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / 3-halobenzoic acid / Halobenzoic acid / Benzoic acid / Anilide / Benzoyl / N-arylamide
show 23 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARG
Uniprot ID
P13631
Uniprot Name
Retinoic acid receptor gamma
Molecular Weight
50341.405 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 15:18 / Updated on December 01, 2017 15:45