p-Aminophenol

Details

• Internal ID: 1f453ba3-2713-4b53-9ae5-d76723af2ed9
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Aniline and substituted anilines
• IUPAC Name: 4-aminophenol
• SMILES (Canonical): C1=CC(=CC=C1N)O
• SMILES (Isomeric): C1=CC(=CC=C1N)O
• InChI: InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2
• InChI Key: PLIKAWJENQZMHA-UHFFFAOYSA-N
• Popularity: 5,142 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₇NO
• Molecular Weight: 109.13 g/mol
• Exact Mass: 109.052763847 g/mol
• Topological Polar Surface Area (TPSA): 46.20 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 123-30-8
• p-aminophenol
• 4-hydroxyaniline
• p-hydroxyaniline
• Phenol, 4-amino-
• Paranol
• 4-aminobenzenol
• Certinal
• Citol
• Azol
• p-Hydroxyphenylamine
• Fouramine P
• Ursol P Base
• Rodinal
• Benzofur P
• Fourrine P Base
• Pelagol P Base
• Tertral P Base
• Ursol P
• 4-Amino-1-hydroxybenzene
• Durafur Brown RB
• Furro P Base
• Nako Brown R
• Renal AC
• Fourrine 84
• Phenol, p-amino-
• Zoba Brown P Base
• 4-AMINO-PHENOL
• Para-aminophenol
• UNAL
• 1-Amino-4-hydroxybenzene
• BASF Ursol P Base
• C.I. Oxidation Base 6
• Pelagol Grey P Base
• p-Aminofenol
• p-Aminofenol [Czech]
• NSC 1545
• Aminophenol, p-
• C.I. 76550
• Paramidophenol
• p-aminobenzenol
• 4-Aminophenol-13C6
• 4-amino phenol
• 4-hydroxybenzenamine
• 4-hydroxyphenylamine
• CCRIS 4146
• CI 76550
• DTXSID3024499
• CHEBI:17602
• HSDB 2640
• EINECS 204-616-2
• MFCD00007869
• UNII-R7P8FRP05V
• R7P8FRP05V
• AI3-14872
• NSC-1545
• p-Aminophenol [UN2512] [Poison]
• NCGC00090816-01
• NCGC00090816-02
• EC 204-616-2
• DTXCID504499
• 4NL
• CAS-123-30-8
• paraaminophenol
• Energol
• Kodelon
• Takatol
• para aminophenol
• p-amino-phenol
• 4-aminophenol B
• para-amino-phenol
• Amino-4 phnol
• 4-hydroxy-aniline
• para-hydroxyaniline
• Para Amino Phenol
• Aminophenol (p-)
• 4-azaniumylphenolate
• Fenol, 4-amino-
• Aminophenol (para-)
• Mesalamine impurity A
• phenol derivative, 9
• CI Oxidation Base 6
• Furro P (Salt/Mix)
• Peltol P (Salt/Mix)
• Pelagol CP (Salt/Mix)
• Futramine P (Salt/Mix)
• Mesalazine EP Impurity A
• WLN: ZR DQ
• bmse000462
• D07MTM
• Epitope ID:117708
• 4-Aminophenol, >=98%
• Buprofezin metabolite BF22
• P-AMINOPHENOL [MI]
• SCHEMBL3424
• CHEMBL1142
• Color Index No. 76550
• Color Index Number 76550
• P-AMINOPHENOL [INCI]
• Colour Index No. 76550
• Durafur Brown R (Salt/Mix)
• MLS001066356
• 4-AMINOPHENOL [HSDB]
• Colour Index Number 76550
• Pelagol Grey CP (Salt/Mix)
• SGCUT00256
• 4-AMINOPHENOL [USP-RS]
• SCHEMBL15663694
• BDBM26195
• NSC1545
• 4- aminophenol (CI 76550)
• BCP25857
• to_000006
• 4-Aminophenol, >=99% (HPLC)
• Tox21_113242
• Tox21_113477
• Tox21_201030
• LS-676
• p-Aminophenol [UN2512] [Poison]
• STK286017
• 4-AMINOPHENOL [USP IMPURITY]
• 4-Aminophenol, technical grade, 95%
• AKOS000119829
• AKOS016371265
• Tox21_113477_1
• AM86423
• CCG-266045
• CS-O-31123
• DB14144
• SB40549
• UN 2512
• NCGC00090816-03
• NCGC00090816-04
• NCGC00090816-05
• NCGC00258583-01
• AS-54109
• SMR000471841
• MESALAZINE IMPURITY A [EP IMPURITY]
• A0384
• CS-0006652
• FT-0617593
• PARACETAMOL IMPURITY K [EP IMPURITY]
• EN300-33645
• C02372
• P17510
• 4-Aminophenol, PESTANAL(R), analytical standard
• AJ-333/25022099
• J-004908
• J-514454
• Q2548040
• Z57127517
• F2190-0438
• 4-Aminophenol, United States Pharmacopeia (USP) Reference Standard
• InChI=1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H
• Mesalazine impurity A, European Pharmacopoeia (EP) Reference Standard
• 4-Aminophenol, 250 mug/mL in acetonitrile, certified reference material, ampule of 1 mL
• 1-Amino-4-hydroxybenzene 4-Amino-1-hydroxybnzene 4-Aminobenzenol 4-amino-pheno
• 4-aminophenol; p-Aminophenol; 1-Amino-4-hydroxybenzene; 4-Amino-1-hydroxybenzene; 4-Hydroxyaniline

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9928	99.28%
Caco-2	+	0.9536	95.36%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Nucleus	0.3808	38.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9469	94.69%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9623	96.23%
P-glycoprotein inhibitior	-	0.9845	98.45%
P-glycoprotein substrate	-	0.9728	97.28%
CYP3A4 substrate	-	0.8502	85.02%
CYP2C9 substrate	-	0.8388	83.88%
CYP2D6 substrate	+	0.4227	42.27%
CYP3A4 inhibition	-	0.8334	83.34%
CYP2C9 inhibition	-	0.8386	83.86%
CYP2C19 inhibition	-	0.7637	76.37%
CYP2D6 inhibition	-	0.9774	97.74%
CYP1A2 inhibition	-	0.7881	78.81%
CYP2C8 inhibition	-	0.9450	94.50%
CYP inhibitory promiscuity	-	0.8152	81.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.5253	52.53%
Carcinogenicity (trinary)	Non-required	0.6087	60.87%
Eye corrosion	-	0.7382	73.82%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.5271	52.71%
Skin corrosion	-	0.7102	71.02%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8787	87.87%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	+	0.7086	70.86%
Respiratory toxicity	-	0.8556	85.56%
Reproductive toxicity	-	0.7889	78.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	II	0.7651	76.51%
Estrogen receptor binding	-	0.6023	60.23%
Androgen receptor binding	+	0.7319	73.19%
Thyroid receptor binding	-	0.7290	72.90%
Glucocorticoid receptor binding	-	0.8304	83.04%
Aromatase binding	-	0.7555	75.55%
PPAR gamma	-	0.5519	55.19%
Honey bee toxicity	-	0.9740	97.40%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.7900	79.00%
Fish aquatic toxicity	-	0.6059	60.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	25118.9 nM	Potency	via CMAUP
CHEMBL2885	P07451	Carbonic anhydrase III	9500 nM	Ki	PMID: 18579385
CHEMBL3025	P23280	Carbonic anhydrase VI	23500 nM	Ki	PMID: 18579385
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	10100 nM	Ki	PMID: 18579385
CHEMBL4801	P29466	Caspase-1	31622.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	3162.3 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	35481.3 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	93.88%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	85.91%	98.35%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	82.96%	95.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.64%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.92%	96.09%

Plants that contains it

• Aconitum carmichaelii
• Camellia oleifera

Cross-Links

• PubChem: 403
• NPASS: NPC70201
• ChEMBL: CHEMBL1142
• LOTUS: LTS0170073
• wikiData: Q2548040