1-Naphthaleneacetic acid

Details

• Internal ID: a1a5533c-1d65-4644-8c09-5be014354a54
• Taxonomy: Benzenoids > Naphthalenes
• IUPAC Name: 2-naphthalen-1-ylacetic acid
• SMILES (Canonical): C1=CC=C2C(=C1)C=CC=C2CC(=O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C=CC=C2CC(=O)O
• 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)
• InChI Key: PRPINYUDVPFIRX-UHFFFAOYSA-N
• Popularity: 9,957 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₀O₂
• Molecular Weight: 186.21 g/mol
• Exact Mass: 186.068079557 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 86-87-3
• 1-NAPHTHALENEACETIC ACID
• 2-(Naphthalen-1-Yl)Acetic Acid
• Naphthalene-1-acetic acid
• Phyomone
• 1-Naphthalene acetic acid
• Transplantone
• NAPHTHALENEACETIC ACID
• Planofix
• Fruitone N
• Fruitofix
• Planofixe
• Celmone
• alpha-Naphthylacetic acid
• Tre-hold
• Stop-Drop
• alpha-Naphthaleneacetic acid
• alpha-NAA
• Tip-Off
• 2-(1-Naphthyl)acetic acid
• Alphaspra
• Klingtite
• Nafusaku
• Primacol
• Rhodofix
• Agronaa
• Biokor
• Etifix
• Pomoxon
• Stafast
• Tekkam
• Vardhak
• Alman
• Rasin
• Liqui-stik
• Pimacol-Sol
• Appl-set
• Rhizopon B
• Niagara-Stik
• naphthalen-1-ylacetic acid
• Nu-Tone
• Naphthylacetic acid
• Floramon
• Hormofix
• Regenasol
• Plucker
• NAA
• Fruit Fix
• 1-Naphthtaleneacetic acid
• NAPHTHALEN-1-YL-ACETIC ACID
• 1-Naphthylessigsaeure
• Naphyl-1-essigsaeure
• STIK
• Caswell No. 589
• 1-NAA
• .alpha.-NAA
• 2-naphthalen-1-ylacetic acid
• .alpha.-Naphthaleneacetic acid
• 1-naphthyl acetic acid
• Phymone
• Germon
• HSDB 2038
• N 10
• Stimolante 66f
• alpha-Naphthyleneacetic acid
• .alpha.-Naphthylacetic acid
• NSC 15772
• Naphthaleneacetic acid (VAN)
• Acide naphtylacetique
• EPA Pesticide Chemical Code 056002
• Acide naphtylacetique [French]
• Naphyl-1-essigsaeure [German]
• 2-(alpha-Naphthyl)ethanoic aid
• Acide naphthylacetique
• Acide naphthylacetique [French]
• ANU
• 2-(alpha-Naphthyl)ethanoic acid
• Kyselina 1-naftyloctova [Czech]
• Naphthyl-1-essigsaeure [German]
• AI3-16113
• Naphthyl-1-essigsaeure
• NAA 800
• a-naphthaleneacetic acid
• alpha-Naphthylessigsaeure [German]
• Kyselina 1-naftyloctova
• alpha-Naphthylessigsaeure
• Acide naphtylacetique [ISO-French]
• EINECS 201-705-8
• alpha-naphthyl acetic acid
• 26445-01-2
• .alpha.-Naphthyleneacetic acid
• CCRIS 8814
• CHEMBL428495
• DTXSID8020915
• UNII-33T7G7757C
• CHEBI:32918
• NSC-15772
• 33T7G7757C
• NCGC00090987-02
• NCGC00090987-03
• NLA
• 1-Naphthylacetic acid (JAN)
• DTXCID60915
• (Naphthalen-1-yl)acetic Acid (1-Naphthylacetic Acid)
• 1-NAPHTHYLACETIC ACID [JAN]
• CAS-86-87-3
• a-naphthylacetic acid
• 1lrh
• 1-naphthyleddikesyre
• naphthyl acetic acid
• MFCD00004046
• NAA (auxin)
• NAFTAL
• Fruitone (Salt/Mix)
• naphthalene acetic acid
• BLX-NLA
• (1-naphthyl)acetic acid
• ?-Naphthaleneacetic Acid
• 1-naphtalene acetic acid
• 2-naphthalyl acetic acid
• Naphtalene-1-acetic acid
• 1-naphthaleneethanoic acid
• I+/--Naphthylacetic acid
• (naphth-1-yl)acetic acid
• D0L8ZX
• RAIZON 05
• .alpha.-Naphthylessigsaeure
• 2-(1-naphtyl)acetic acid
• Oprea1_374703
• SCHEMBL35925
• WLN: L66J B1VQ
• MLS001055368
• (Naphthalen-1-yl)acetic acid
• [3H]-NAA
• 1-Naphthaleneacetic acid, 97%
• 1-Naphthaleneacetic acid (solid)
• AMY3378
• Anti-allergy drug, NicOx/Biolipox
• HMS1649K07
• HMS3039O06
• HMS3604I22
• NO-donating therapeutics, Biolipox
• NAPHTHYLACETIC ACID [MART.]
• NCX-1510
• NSC15772
• Tox21_111051
• Tox21_400007
• AC-640
• BBL011795
• BDBM50022186
• s9362
• STL163395
• (1-Naphthyl)acetic acid, BSI, ISO
• 1-NAPHTHALENEACETIC ACID [MI]
• AKOS000104252
• Tox21_111051_1
• 1-Naphthalene-4-t-acetic acid (9CI)
• CCG-266475
• CS-6285
• DB01750
• FS-2548
• LS-7536
• 1-NAPHTHALENEACETIC ACID [INCI]
• ALPHA-NAPHTHYLACETIC ACID [HSDB]
• s12283
• NCGC00090987-01
• NCGC00090987-04
• NCGC00090987-05
• NO-donating therapeutics, Biolipox/Nicox
• 1-Naphthaleneacetic acid, technical grade
• HY-18570
• N 40
• PD008449
• SMR000677931
• 1-Naphthaleneacetic acid (7CI,8CI,9CI)
• 1-NAPHTHALENEACETIC ACID [WHO-DD]
• 2-(.ALPHA.-NAPHTHYL)ETHANOIC ACID
• 2-(1-naphthyl)acetate;1-Naphthylacetic acid
• FT-0608129
• N0005
• EN300-18112
• D01558
• N-1420
• NO-donating allergy therapeutics, Biolipox/Nicox
• A841863
• AE-508/13205220
• Q161660
• J-610083
• NO-donating respiratory therapeutics, NicOx/Biolipox
• Z57169437
• F0020-1890
• 1-Naphthaleneacetic acid, PESTANAL(R), analytical standard
• NAPHAZOLINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• OX-NLA (nasal/liposomal formulation, allergic rhinitis/rhinitis)
• 1-Naphthylacetic acid, 1 mg/mL, BioReagent, plant cell culture tested
• OX-NLA (nasal/liposomal formulation, allergic rhinitis/rhinitis), Meda
• 1-Naphthaleneacetic acid, plant cell culture tested, BioReagent, >=95%, crystalline
• 3-(3-tert-Butoxycarbonylamino-piperidin-1-yl)-2-methyl-propionicacidmethylester
• Liposomal nitric oxide-donating cetirizine derivative (nasal, rhinitis), Biolipox
• Nitric oxide-donating cetirizine derivative (liposomal, intranasal, rhinitis), Orexo

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.9242	92.42%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Plasma membrane	0.4251	42.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9631	96.31%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7987	79.87%
P-glycoprotein inhibitior	-	0.9798	97.98%
P-glycoprotein substrate	-	0.9827	98.27%
CYP3A4 substrate	-	0.6928	69.28%
CYP2C9 substrate	+	0.6248	62.48%
CYP2D6 substrate	-	0.7786	77.86%
CYP3A4 inhibition	-	0.9677	96.77%
CYP2C9 inhibition	-	0.9729	97.29%
CYP2C19 inhibition	-	0.9576	95.76%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	+	0.8636	86.36%
CYP2C8 inhibition	-	0.9168	91.68%
CYP inhibitory promiscuity	-	0.9407	94.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6924	69.24%
Carcinogenicity (trinary)	Non-required	0.6727	67.27%
Eye corrosion	-	0.9536	95.36%
Eye irritation	+	0.9817	98.17%
Skin irritation	+	0.7810	78.10%
Skin corrosion	-	0.7525	75.25%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7243	72.43%
Micronuclear	-	0.6991	69.91%
Hepatotoxicity	+	0.6779	67.79%
skin sensitisation	+	0.7160	71.60%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8236	82.36%
Acute Oral Toxicity (c)	III	0.8742	87.42%
Estrogen receptor binding	-	0.7274	72.74%
Androgen receptor binding	-	0.8756	87.56%
Thyroid receptor binding	-	0.7147	71.47%
Glucocorticoid receptor binding	+	0.6501	65.01%
Aromatase binding	+	0.5583	55.83%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.9737	97.37%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.8963	89.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	10000 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.00%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.83%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	90.13%	90.17%
CHEMBL2581	P07339	Cathepsin D	88.23%	98.95%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	86.96%	87.50%
CHEMBL230	P35354	Cyclooxygenase-2	83.82%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.41%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.02%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	82.77%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.63%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	82.44%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.15%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.67%	94.62%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 6862
• NPASS: NPC172925
• ChEMBL: CHEMBL428495
• LOTUS: LTS0247239
• wikiData: Q161660