4-Aminosalicylic acid

Details

• Internal ID: b2afa686-0f8a-458c-820f-8a1fc72158ca
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Aminosalicylic acids and derivatives > Aminosalicylic acids
• IUPAC Name: 4-amino-2-hydroxybenzoic acid
• SMILES (Canonical): C1=CC(=C(C=C1N)O)C(=O)O
• SMILES (Isomeric): C1=CC(=C(C=C1N)O)C(=O)O
• InChI: InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
• InChI Key: WUBBRNOQWQTFEX-UHFFFAOYSA-N
• Popularity: 5,960 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14 g/mol
• Exact Mass: 153.042593085 g/mol
• Topological Polar Surface Area (TPSA): 83.60 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 65-49-6
• 4-Amino-2-hydroxybenzoic acid
• Aminosalicylic acid
• P-AMINOSALICYLIC ACID
• Paser
• Paramycin
• Parasal
• Parasalindon
• Aminopar
• Deapasil
• Apacil
• Gabbropas
• Parasalicil
• Pasnodia
• Aminox
• Entepas
• Osacyl
• Pamacyl
• Pasalon
• Pasara
• Pasdium
• Pasmed
• Pasolac
• Propasa
• Pasem
• Pasa
• Benzoic acid, 4-amino-2-hydroxy-
• Sanipirol-4
• APAS
• Para-Pas
• PASK
• 2-Hydroxy-4-aminobenzoic acid
• Hellipidyl
• para-Amino salicylic acid
• Pascorbic
• PAS (acid)
• aminosalicylate
• Aminosalyl
• Helipidyl
• Paser Granules
• Salicylic acid, 4-amino-
• 3-Hydroxy-4-carboxyaniline
• Granupas
• NIH 2939
• NSC 2083
• A 1909
• Aminosalicylic Acid [USP]
• NSC-2083
• CHEBI:27565
• NSC2083
• Aminosalicylic acid (USP)
• 5B2658E0N2
• DTXSID2022591
• 4-14-00-01967 (Beilstein Handbook Reference)
• Acid, Aminosalicylic
• p Aminosalicylic Acid
• 4 Aminosalicylic Acid
• para Aminosalicylic Acid
• RefChem:912358
• Alumino 4 Aminosalicylic Acid
• DTXCID302591
• p Aminosalicylic Acid Monolithium Salt
• p Aminosalicylic Acid Monopotassium Salt
• 200-613-5
• Rezipas
• Para-aminosalicylic acid
• Pamisyl
• MFCD00007789
• PAS
• Kyselina p-aminosalicylova
• Amino-pas
• Sanipriol-4
• 4-Aminosalicylate
• 4-Asa
• 4-amino-2-hydroxy-benzoic acid
• p-amino salicylic acid
• MLS000069418
• SMR000059110
• PASKALIUM
• MLS000069579
• PAS (VAN)
• 4-Aminosalicylicacid
• Benzoic acid, 4-aminohydroxy-
• HSDB 3203
• 4-amino salicylic acid
• Kyselina p-aminosalicylova [Czech]
• SR-01000002990
• SMR000058830
• EINECS 200-613-5
• Mesalazine EP Impurity E
• BRN 0473071
• P.A.S
• Aminosalicylic
• AI3-50142
• UNII-5B2658E0N2
• ISONICOTINIC ACID HYDRAZIDE P-AMINOSALICYLATE SALT
• Pamisyl (TN)
• Paser (TN)
• 4-Aminosalicyclic acid
• Spectrum_000042
• .gamma.-Aminosalicylate
• Opera_ID_614
• Spectrum2_000001
• Spectrum3_000297
• Spectrum4_000145
• Spectrum5_000804
• para-amino-salicyclic acid
• WLN: ZR CQ DVQ
• Salicyclic acid, 4-amino-
• SCHEMBL2262
• CHEMBL1169
• BSPBio_001834
• KBioGR_000590
• KBioSS_000422
• MLS001148121
• 4-Aminosalicylic acid, 99%
• BIDD:GT0175
• DivK1c_000350
• 4-amino-2-hydroxobenzoic acid
• SPBio_000001
• orb1309076
• SCHEMBL4242531
• p-Aminosalicylic acid STANDARD
• SCHEMBL29450213
• BDBM48319
• GTPL13652
• HMS501B12
• HY-I0447R
• KBio1_000350
• KBio2_000422
• KBio2_002990
• KBio2_005558
• KBio3_001334
• 4-Aminobenzoic acid, 2-hydroxy-
• 4-Aminosalicylic acid (Standard)
• 4-azanyl-2-oxidanyl-benzoic acid
• cid_11988145
• NINDS_000350
• AMINOSALICYLIC ACID [HSDB]
• HMS2090I07
• HMS2093L14
• HMS2236I04
• HMS3371A17
• HMS3715M08
• HMS5084P13
• KUC106682N
• AMINOSALICYLIC ACID [VANDF]
• P-AMINOSALICYLIC ACID [MI]
• AMINOSALICYLIC ACID [MART.]
• BCP18565
• HY-I0447
• AMINOSALICYLIC ACID [USP-RS]
• AMINOSALICYLIC ACID [WHO-DD]
• CCG-39969
• s5211
• SBB056794
• STL163955
• AKOS000121200
• CS-W023102
• DB00233
• FA10792
• PB47849
• 4-AMINO,2-HYDROXY-BENZOIC ACID
• IDI1_000350
• AMINOSALICYLIC ACID [ORANGE BOOK]
• NCGC00018110-01
• NCGC00018110-02
• NCGC00018110-03
• NCGC00018110-04
• AC-12894
• AS-11043
• SY001079
• AMINOSALICYLIC ACID [USP MONOGRAPH]
• KSC-11-207-13
• SBI-0051279.P003
• SBI-0051279.P004
• DB-054818
• MESALAZINE IMPURITY E [EP IMPURITY]
• A0420
• NS00010608
• ST50824394
• EN300-18730
• C02518
• D00162
• NEOPASALATE COMPONENT AMINOSALICYLIC ACID
• P17508
• AB00051913-20
• F078671
• Q229924
• SR-01000002990-4
• SR-01000002990-6
• 4-Aminosalicylic acid, Vetec(TM) reagent grade, 99%
• BRD-K80267133-001-17-7
• BRD-K80267133-001-18-5
• BRD-K80267133-001-19-3
• Z90121065
• F2191-0245
• para-aminosalicylic acid;Aminosalicylic acid;4-aminosalicylate
• Aminosalicylic acid, United States Pharmacopeia (USP) Reference Standard
• 4-Aminosalicylic acid, Pharmaceutical Secondary Standard; Certified Reference Material
• InChI=1/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9824	98.24%
Caco-2	+	0.8122	81.22%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6152	61.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9677	96.77%
OATP1B3 inhibitior	+	0.9621	96.21%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9768	97.68%
P-glycoprotein inhibitior	-	0.9833	98.33%
P-glycoprotein substrate	-	0.9755	97.55%
CYP3A4 substrate	-	0.8664	86.64%
CYP2C9 substrate	+	0.5023	50.23%
CYP2D6 substrate	-	0.8508	85.08%
CYP3A4 inhibition	-	0.7324	73.24%
CYP2C9 inhibition	-	0.8281	82.81%
CYP2C19 inhibition	+	0.5778	57.78%
CYP2D6 inhibition	-	0.9627	96.27%
CYP1A2 inhibition	-	0.8645	86.45%
CYP2C8 inhibition	-	0.9519	95.19%
CYP inhibitory promiscuity	-	0.9157	91.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7171	71.71%
Carcinogenicity (trinary)	Non-required	0.7288	72.88%
Eye corrosion	-	0.9886	98.86%
Eye irritation	+	0.9973	99.73%
Skin irritation	-	0.6197	61.97%
Skin corrosion	-	0.9890	98.90%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8893	88.93%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	+	0.6017	60.17%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6334	63.34%
Acute Oral Toxicity (c)	III	0.8063	80.63%
Estrogen receptor binding	-	0.7433	74.33%
Androgen receptor binding	-	0.5071	50.71%
Thyroid receptor binding	-	0.5474	54.74%
Glucocorticoid receptor binding	-	0.7256	72.56%
Aromatase binding	-	0.7587	75.87%
PPAR gamma	+	0.6682	66.82%
Honey bee toxicity	-	0.9832	98.32%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	+	0.7549	75.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 17782.8 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.93%	91.11%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	89.69%	95.48%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.67%	94.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.58%	95.56%
CHEMBL3194	P02766	Transthyretin	88.43%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.40%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	85.49%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.86%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.82%	94.45%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.63%	95.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.08%	95.50%

Plants that contains it

• Senecio scandens

Cross-Links

• PubChem: 4649
• NPASS: NPC301702
• ChEMBL: CHEMBL1169