1-naphthaleneacetic acid

Identification

Name
1-naphthaleneacetic acid
Accession Number
DB01750  (EXPT02353)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 1-Naphthylacetic acid
  • NAA
  • naphthalen-1-yl-acetic acid
  • naphthalene-1-acetic acid
  • α-NAA
  • α-naphthaleneacetic acid
External IDs
N 10 / N 40 / NSC-15772
Categories
Not Available
UNII
33T7G7757C
CAS number
86-87-3
Weight
Average: 186.2066
Monoisotopic: 186.068079564
Chemical Formula
C12H10O2
InChI Key
PRPINYUDVPFIRX-UHFFFAOYSA-N
InChI
InChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
IUPAC Name
2-(naphthalen-1-yl)acetic acid
SMILES
OC(=O)CC1=C2C=CC=CC2=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
US-phase kinase-associated protein 1Not 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
Human Metabolome Database
HMDB32708
KEGG Drug
D01558
KEGG Compound
C13014
PubChem Compound
6862
PubChem Substance
46508218
ChemSpider
6601
BindingDB
50022186
ChEBI
32918
ChEMBL
CHEMBL428495
HET
NLA
PDB Entries
1lrh / 2p1o / 3n8i / 4o1y

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
PropertyValueSource
melting point (°C)135 °CPhysProp
water solubility420 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.24SANGSTER (1993)
pKa4.23 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility0.11 mg/mLALOGPS
logP2.97ALOGPS
logP2.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.82 m3·mol-1ChemAxon
Polarizability19.42 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9932
Blood Brain Barrier+0.9524
Caco-2 permeable+0.8528
P-glycoprotein substrateNon-substrate0.7164
P-glycoprotein inhibitor INon-inhibitor0.9272
P-glycoprotein inhibitor IINon-inhibitor0.9621
Renal organic cation transporterNon-inhibitor0.9033
CYP450 2C9 substrateNon-substrate0.7762
CYP450 2D6 substrateNon-substrate0.9272
CYP450 3A4 substrateNon-substrate0.7625
CYP450 1A2 substrateInhibitor0.8636
CYP450 2C9 inhibitorNon-inhibitor0.9729
CYP450 2D6 inhibitorNon-inhibitor0.9392
CYP450 2C19 inhibitorNon-inhibitor0.9576
CYP450 3A4 inhibitorNon-inhibitor0.9677
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9407
Ames testNon AMES toxic0.7795
CarcinogenicityNon-carcinogens0.7404
BiodegradationNot ready biodegradable0.6522
Rat acute toxicity2.2385 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9474
hERG inhibition (predictor II)Non-inhibitor0.9353
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
GC-MS Spectrum - EI-BGC-MSsplash10-0006-0900000000-217de62c6bdb645dae35
GC-MS Spectrum - EI-BGC-MSsplash10-0006-1900000000-782f3a027c45e64394b3
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 naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Naphthalene / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group / Aromatic homopolycyclic compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
naphthylacetic acid (CHEBI:32918) / Auxins (C13014)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin-protein transferase activity
Specific Function
Essential component of the SCF (SKP1-CUL1-F-box protein) ubiquitin ligase complex, which mediates the ubiquitination of proteins involved in cell cycle progression, signal transduction and transcri...
Gene Name
SKP1
Uniprot ID
P63208
Uniprot Name
S-phase kinase-associated protein 1
Molecular Weight
18657.86 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 June 13, 2005 07:24 / Updated on November 09, 2017 03:04