N-Phenyl-1-naphthylamine

Details

• Internal ID: cccd3671-df89-4f9f-a0b1-a81381f3f394
• Taxonomy: Benzenoids > Naphthalenes
• IUPAC Name: N-phenylnaphthalen-1-amine
• SMILES (Canonical): C1=CC=C(C=C1)NC2=CC=CC3=CC=CC=C32
• SMILES (Isomeric): C1=CC=C(C=C1)NC2=CC=CC3=CC=CC=C32
• InChI: InChI=1S/C16H13N/c1-2-9-14(10-3-1)17-16-12-6-8-13-7-4-5-11-15(13)16/h1-12,17H
• InChI Key: XQVWYOYUZDUNRW-UHFFFAOYSA-N
• Popularity: 627 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.28 g/mol
• Exact Mass: 219.104799419 g/mol
• Topological Polar Surface Area (TPSA): 12.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.58
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 90-30-2
• N-phenylnaphthalen-1-amine
• 1-Anilinonaphthalene
• PANA
• N-(1-Naphthyl)aniline
• Antioxidant PAN
• Neozone A
• 1-Naphthalenamine, N-phenyl-
• Phenylnaphthylamine
• Nonox A
• Aceto PAN
• Vulkanox PAN
• Phenyl-1-naphthylamine
• N-Phenyl-alpha-naphthylamine
• 1-Naphthylamine, N-phenyl-
• Additin 30
• 1-naphthylphenylamine
• N-1-Naphthylaniline
• Amoco 32
• Naphthalen-1-yl-phenyl-amine
• Antigene PAN
• N-Phenyl-1-naphthalenamine
• alpha-Naphthylphenylamine
• N-Fenyl-1-aminonaftalen
• Naugard PANA
• Nocrac PA
• NSC 2622
• C.I. 44050
• Nonox AN
• N-Phenyl-1-aminonaphthalene
• 1-(n-phenylamino)naphthalene
• CCRIS 4701
• Fenyl-alpha-naftylamin [Czech]
• DTXSID2025892
• Fenyl-alpha-naftylamin
• CHEBI:34876
• HSDB 7232
• N-Fenyl-1-aminonaftalen [Czech]
• phenyl alpha naphthylamine
• EINECS 201-983-0
• .alpha.-Naphthylphenylamine
• .alpha.-Phenylnaphthylamine
• BRN 2211174
• Phenyl-.alpha.-naphthylamine
• n-(1-naphthyl)-n-phenylamine
• AI3-00528
• MLS002415761
• MLS002637634
• CHEMBL170408
• N-phenyl-N-(1-naphthyl)amine
• N-Phenyl-.alpha.-naphthylamine
• UNII-5I112077IN
• NSC-2622
• 5I112077IN
• SMR000112177
• EC 201-983-0
• 4-12-00-03015 (Beilstein Handbook Reference)
• DTXCID605892
• CAS-90-30-2
• N-Phenylnaphthylamine
• Algerite
• Antioxidant A
• Antigene PA
• Neozon A
• 1-anilinonaftaleno
• Alpha Natphthylamine
• N-1-Naphthylanilin
• Irganox L 05
• 1-phenylaminonaphthalene
• 3s0b
• n-phenyl-1-napthylamine
• 1-Naphthyl phenyl amine
• N-phenyl-l-naphthylamine
• T 531 (antioxidant)
• alpha-naphthyl-phenylamine
• Fenyl-.alpha.-naftylamin
• 1-(fenilamino) naftaleno
• Phenyl-alpha-naphthylamine
• 1-Naftilamina, N-fenil-
• N-Phenyl-1-napthyl Amine
• 1-(Phenylamino)naphthalene
• 1-naftalenamina, n-fenil-
• Naphthalenamine, N-phenyl-
• WLN: L66J BMR
• 1-(N-fenilamino) naftaleno
• SCHEMBL19796
• BIDD:ER0663
• SCHEMBL7751770
• NSC2622
• HMS2270J09
• Tox21_202073
• Tox21_303075
• BDBM50504083
• MFCD00003878
• STK182583
• 1-Naphthylamine N-phenyl-(7CI8CI)
• AKOS003386028
• 1-Naphthylamine N-phenyl-(7CI 8CI)
• CS-W010472
• LS-1909
• NCGC00091327-01
• NCGC00091327-02
• NCGC00091327-03
• NCGC00091327-04
• NCGC00256930-01
• NCGC00259622-01
• AS-17486
• 1-NAPHTHYLAMINE, N-PHENYL- [HSDB]
• FT-0657709
• P0197
• T 531
• EN300-365758
• N-Phenyl-1-naphthylamine, reagent grade, 98%
• SR-01000868875
• SR-01000868875-2
• W-100333
• Q10859671
• InChI=1/C16H13N/c1-2-9-14(10-3-1)17-16-12-6-8-13-7-4-5-11-15(13)16/h1-12,17

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	+	0.9074	90.74%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Lysosomes	0.8436	84.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9641	96.41%
OATP1B3 inhibitior	+	0.9603	96.03%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5940	59.40%
P-glycoprotein inhibitior	-	0.9373	93.73%
P-glycoprotein substrate	-	0.9613	96.13%
CYP3A4 substrate	-	0.7241	72.41%
CYP2C9 substrate	-	0.8132	81.32%
CYP2D6 substrate	+	0.5900	59.00%
CYP3A4 inhibition	-	0.8993	89.93%
CYP2C9 inhibition	-	0.8160	81.60%
CYP2C19 inhibition	+	0.8549	85.49%
CYP2D6 inhibition	+	0.5896	58.96%
CYP1A2 inhibition	+	0.8962	89.62%
CYP2C8 inhibition	+	0.4532	45.32%
CYP inhibitory promiscuity	+	0.7604	76.04%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5400	54.00%
Carcinogenicity (trinary)	Non-required	0.6387	63.87%
Eye corrosion	-	0.6822	68.22%
Eye irritation	+	0.9862	98.62%
Skin irritation	+	0.8624	86.24%
Skin corrosion	-	0.7931	79.31%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5949	59.49%
Micronuclear	+	0.7469	74.69%
Hepatotoxicity	+	0.5698	56.98%
skin sensitisation	+	0.7419	74.19%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	-	0.8222	82.22%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	+	0.5559	55.59%
Acute Oral Toxicity (c)	III	0.8671	86.71%
Estrogen receptor binding	+	0.9587	95.87%
Androgen receptor binding	+	0.8762	87.62%
Thyroid receptor binding	+	0.7584	75.84%
Glucocorticoid receptor binding	+	0.6766	67.66%
Aromatase binding	+	0.9468	94.68%
PPAR gamma	+	0.9108	91.08%
Honey bee toxicity	-	0.9501	95.01%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.9200	92.00%
Fish aquatic toxicity	+	0.9518	95.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	10000 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	31622.8 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	3.2 nM; 3.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	96.98%	90.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	93.02%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.51%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.98%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.93%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.78%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	87.54%	89.63%
CHEMBL2916	O14746	Telomerase reverse transcriptase	86.44%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.70%	86.33%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.50%	96.67%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.81%	96.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	82.76%	93.81%
CHEMBL3401	O75469	Pregnane X receptor	82.63%	94.73%
CHEMBL2637	P53779	c-Jun N-terminal kinase 3	82.61%	92.75%
CHEMBL3959	P16083	Quinone reductase 2	81.81%	89.49%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	81.40%	94.67%

Plants that contains it

• Arundo donax
• Pogostemon cablin

Cross-Links

• PubChem: 7013
• NPASS: NPC79618
• ChEMBL: CHEMBL170408
• LOTUS: LTS0240149
• wikiData: Q10859671