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Identification
- Summary
1-naphthaleneacetic acid is a drug used to treat digestive problems from excessive fat consumption and functional disorders of the gallbladder and bile ducts.
- Generic Name
- 1-naphthaleneacetic acid
- DrugBank Accession Number
- DB01750
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 1-naphthaleneacetic acid (DB01750)
- Weight
- Average: 186.2066
Monoisotopic: 186.068079564 - Chemical Formula
- C12H10O2
- 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
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Bile duct disorders Combination Product in combination with: 2-(p-Tolyl)ethyl nicotinate (DB16617) ••• ••• ••••••• ••••• •••••• Used in combination to treat Gallbladder disorders Combination Product in combination with: 2-(p-Tolyl)ethyl nicotinate (DB16617) ••• ••• ••••••• ••••• •••••• Used in combination to treat Digestion disorder caused by fat digestion Combination Product in combination with: 2-(p-Tolyl)ethyl nicotinate (DB16617) ••• ••• ••••••• ••••• •••••• - Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism US-phase kinase-associated protein 1 Not Available Humans - 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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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
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Galle - Donau - Dragees 1-naphthaleneacetic acid (75 mg) + 2-(p-Tolyl)ethyl nicotinate (37.5 mg) Tablet, sugar coated Oral Phafag Pharma Research & Trading Gmb H 1962-04-06 Not applicable Austria 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Naphthalene / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- naphthylacetic acid (CHEBI:32918) / Auxins (C13014)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 33T7G7757C
- CAS number
- 86-87-3
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0032708
- KEGG Drug
- D01558
- KEGG Compound
- C13014
- PubChem Compound
- 6862
- PubChem Substance
- 46508218
- ChemSpider
- 6601
- BindingDB
- 50022186
- ChEBI
- 32918
- ChEMBL
- CHEMBL428495
- ZINC
- ZINC000000391809
- PDBe Ligand
- NLA
- Wikipedia
- 1-Naphthaleneacetic_acid
- PDB Entries
- 1lrh / 2p1o / 3n8i / 4o1y
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, sugar coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 135 °C PhysProp water solubility 420 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.24 SANGSTER (1993) pKa 4.23 (at 25 °C) KORTUM,G ET AL (1961) - Predicted Properties
Property Value Source Water Solubility 0.11 mg/mL ALOGPS logP 2.97 ALOGPS logP 2.6 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 4.75 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 53.82 m3·mol-1 Chemaxon Polarizability 19.42 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9932 Blood Brain Barrier + 0.9524 Caco-2 permeable + 0.8528 P-glycoprotein substrate Non-substrate 0.7164 P-glycoprotein inhibitor I Non-inhibitor 0.9272 P-glycoprotein inhibitor II Non-inhibitor 0.9621 Renal organic cation transporter Non-inhibitor 0.9033 CYP450 2C9 substrate Non-substrate 0.7762 CYP450 2D6 substrate Non-substrate 0.9272 CYP450 3A4 substrate Non-substrate 0.7625 CYP450 1A2 substrate Inhibitor 0.8636 CYP450 2C9 inhibitor Non-inhibitor 0.9729 CYP450 2D6 inhibitor Non-inhibitor 0.9392 CYP450 2C19 inhibitor Non-inhibitor 0.9576 CYP450 3A4 inhibitor Non-inhibitor 0.9677 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9407 Ames test Non AMES toxic 0.7795 Carcinogenicity Non-carcinogens 0.7404 Biodegradation Not ready biodegradable 0.6522 Rat acute toxicity 2.2385 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9474 hERG inhibition (predictor II) Non-inhibitor 0.9353
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 144.7600886 predictedDarkChem Lite v0.1.0 [M-H]- 136.85196 predictedDeepCCS 1.0 (2019) [M+H]+ 139.24751 predictedDeepCCS 1.0 (2019) [M+Na]+ 146.29832 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 transcription. In the SCF complex, serves as an adapter that links the F-box protein to CUL1. The functional specificity of the SCF complex depends on the F-box protein as substrate recognition component. SCF(BTRC) and SCF(FBXW11) direct ubiquitination of CTNNB1 and participate in Wnt signaling. SCF(FBXW11) directs ubiquitination of phosphorylated NFKBIA. SCF(BTRC) directs ubiquitination of NFKBIB, NFKBIE, ATF4, SMAD3, SMAD4, CDC25A, FBXO5, CEP68 and probably NFKB2 (PubMed:25704143). SCF(SKP2) directs ubiquitination of phosphorylated CDKN1B/p27kip and is involved in regulation of G1/S transition. SCF(SKP2) directs ubiquitination of ORC1, CDT1, RBL2, ELF4, CDKN1A, RAG2, FOXO1A, and probably MYC and TAL1. SCF(FBXW7) directs ubiquitination of cyclin E, NOTCH1 released notch intracellular domain (NICD), and probably PSEN1. SCF(FBXW2) directs ubiquitination of GCM1. SCF(FBXO32) directs ubiquitination of MYOD1. SCF(FBXO7) directs ubiquitination of BIRC2 and DLGAP5. SCF(FBXO33) directs ubiquitination of YBX1. SCF(FBXO11) directs ubiquitination of BCL6 and DTL but does not seem to direct ubiquitination of TP53. SCF(BTRC) mediates the ubiquitination of NFKBIA at 'Lys-21' and 'Lys-22'; the degradation frees the associated NFKB1-RELA dimer to translocate into the nucleus and to activate transcription. SCF(CCNF) directs ubiquitination of CCP110. SCF(FBXL3) and SCF(FBXL21) direct ubiquitination of CRY1 and CRY2. SCF(FBXO9) directs ubiquitination of TTI1 and TELO2. SCF(FBXO10) directs ubiquitination of BCL2
- Specific Function
- Beta-catenin binding
- Gene Name
- SKP1
- Uniprot ID
- P63208
- Uniprot Name
- S-phase kinase-associated protein 1
- Molecular Weight
- 18657.86 Da
References
- 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 June 13, 2005 13:24 / Updated at September 28, 2023 05:40