Sulfanilic acid

Details

• Internal ID: 36231567-de9f-479c-8727-f550ec3c1bd5
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzenesulfonic acids and derivatives
• IUPAC Name: 4-aminobenzenesulfonic acid
• SMILES (Canonical): C1=CC(=CC=C1N)S(=O)(=O)O
• SMILES (Isomeric): C1=CC(=CC=C1N)S(=O)(=O)O
• InChI: InChI=1S/C6H7NO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
• InChI Key: HVBSAKJJOYLTQU-UHFFFAOYSA-N
• Popularity: 3,098 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₇NO₃S
• Molecular Weight: 173.19 g/mol
• Exact Mass: 173.01466426 g/mol
• Topological Polar Surface Area (TPSA): 88.80 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 4-Aminobenzenesulfonic acid
• 121-57-3
• Sulphanilic acid
• p-Aminobenzenesulfonic acid
• Aniline-4-sulfonic acid
• Sulfanilsaeure
• Aniline-p-sulfonic acid
• Aniline-p-sulphonic acid
• Benzenesulfonic acid, 4-amino-
• p-Aminophenylsulfonic acid
• p-Anilinesulfonic acid
• Kyselina sulfanilova
• 4-Sulfoaniline
• 4-Sulfanilic acid
• CHEBI:27500
• NSC 7170
• CCRIS 4576
• p-sulfoaniline
• Sulfanilsaeure [German]
• HSDB 5590
• EINECS 204-482-5
• p-Sulfoaniline-d4
• Kyselina sulfanilova [Czech]
• 4-aminobenzene-1-sulfonic acid
• AI3-15414
• UNII-434Z8C2635
• NSC-7170
• 4-aminophenylsulfonic acid
• C6H7NO3S
• p-aminobenzene sulfonic acid
• 4-aminobenzene sulfonic acid
• 1-aminobenzene-4-sulfonic acid
• 434Z8C2635
• CHEMBL1566888
• DTXSID6024464
• EC 204-482-5
• MFCD00007886
• 71949-32-1
• 97675-28-0
• SULFANILIC ACID (USP-RS)
• SULFANILIC ACID [USP-RS]
• MESALAZINE IMPURITY O (EP IMPURITY)
• MESALAZINE IMPURITY O [EP IMPURITY]
• SULFADIAZINE IMPURITY B (EP IMPURITY)
• SULFADIAZINE IMPURITY B [EP IMPURITY]
• SUFANILIC ACID
• SULFADIMIDINE IMPURITY F (EP IMPURITY)
• SULFADIMIDINE IMPURITY F [EP IMPURITY]
• 4-Aminobenzenesulphonic Acid (Sulphanilic Acid)
• SULFADIMETHOXINE IMPURITY D (EP IMPURITY)
• SULFADIMETHOXINE IMPURITY D [EP IMPURITY]
• SULFAMETHOXAZOLE IMPURITY D (EP IMPURITY)
• SULFAMETHOXAZOLE IMPURITY D [EP IMPURITY]
• P-SULFANILIC ACID
• ANILINE P-SULFONIC ACID
• SULFADIMETHOXINE SODIUM FOR VETERINARY USE IMPURITY D (EP IMPURITY)
• SULFADIMETHOXINE SODIUM FOR VETERINARY USE IMPURITY D [EP IMPURITY]
• Sulfanilic acid;
• Acide sulfanilique
• p-sulphanilic acid
• 4-AMINOBENZENESULPHONIC ACID
• Benzenesulfonic acid, 4-amino-, diazotized, coupled with 5,5'-oxybis(1,3-benzenediol), sodium salt
• Benzenesulfonic acid, 4-amino-, diazotized, coupled with 5,5'-oxybis[1,3-benzenediol], sodium salt
• Benzenesulfonic acid, 4-amino-, diazotized, coupled with diazotized 4-((4-aminophenyl)azo)benzenesulfonic acid and resorcinol
• Benzenesulfonic acid, 4-amino-, diazotized, coupled with diazotized 4-[(4-aminophenyl)azo]benzenesulfonic acid and resorcinol
• Sulfanilic acid, 99%
• Sulfanilic Acid Anhydrous
• bmse000726
• Epitope ID:122241
• p-aminobenzenesulphonic acid
• 4-aminobenzene-sulfonic acid
• SCHEMBL24407
• SULFANILIC ACID [MI]
• 4-Amino benzenesulphonic acid
• Sulfanilic acid, >=99.0%
• SULFANILIC ACID [HSDB]
• 4-amino-1-benzenesulfonic acid
• DTXCID604464
• Sulfanilic acid, 98%, tech.
• NSC7170
• PARA-ANILINE SULFONIC ACID
• Sulfanilate Zinc (sulfanilic acid)
• EINECS 276-203-5
• EINECS 285-231-7
• EINECS 286-256-6
• EINECS 290-689-6
• EINECS 290-691-7
• EINECS 305-460-9
• EINECS 307-598-5
• Nitrate Reagent B, for microbiology
• BBL011603
• BDBM50443531
• LS-650
• STK661383
• Sulfanilic acid, ACS reagent, 99%
• AKOS000118732
• AM91128
• NCGC00090886-01
• NCGC00090886-02
• 85049-60-1
• 85203-66-3
• 90218-16-9
• 90218-18-1
• 94552-15-5
• AC-12565
• VS-02984
• Sulfanilic Acid [for Biochemical Research]
• Sulfanilic acid, p.a., 98.0-102.0%
• FT-0674701
• S0120
• U0107
• EN300-19269
• C06335
• E80415
• Sulfanilic acid, Vetec(TM) reagent grade, 99%
• Q253746
• Sulfanilic acid, puriss. p.a., >=99.0% (T)
• J-004536
• 4-Aminobenzenesulfonic acid 100 microg/mL in Methanol
• Sulfanilic acid, JIS special grade, 99.0-100.5%
• F0001-0346
• Z104473374
• Sulfanilic acid, United States Pharmacopeia (USP) Reference Standard
• Benzenesulfonic acid, 4-amino-, diazotized, coupled with m-phenylenediamine
• Sulfanilic acid, 99.0-100.5%, suitable for determination of nitroxide
• Benzenesulfonic acid, 4-amino-, diazotized, coupled with C.I. Natural Yellow 11
• Benzenesulfonic acid,4-amino-,diazotized,coupled with dyer's mulberry extract
• InChI=1/C6H7NO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H,8,9,10
• Sulfanilic Acid, Pharmaceutical Secondary Standard; Certified Reference Material
• Benzenesulfonic acid, 4-amino-, diazotized, coupled with 4-methyl-1,3-benzenediamine and m-phenylenediamine, sodium salt
• Benzenesulfonic acid,4-amino-,diazotized,coupled with 5,5'-oxybis[1,3-benzenediol],sodium salt

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6186	61.86%
Caco-2	+	0.8462	84.62%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Plasma membrane	0.5091	50.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9873	98.73%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9651	96.51%
P-glycoprotein inhibitior	-	0.9787	97.87%
P-glycoprotein substrate	-	0.9765	97.65%
CYP3A4 substrate	-	0.8441	84.41%
CYP2C9 substrate	+	0.6131	61.31%
CYP2D6 substrate	-	0.6988	69.88%
CYP3A4 inhibition	-	0.9874	98.74%
CYP2C9 inhibition	-	0.8393	83.93%
CYP2C19 inhibition	-	0.8056	80.56%
CYP2D6 inhibition	-	0.9532	95.32%
CYP1A2 inhibition	-	0.9571	95.71%
CYP2C8 inhibition	-	0.9967	99.67%
CYP inhibitory promiscuity	-	0.9723	97.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.8406	84.06%
Carcinogenicity (trinary)	Non-required	0.6215	62.15%
Eye corrosion	+	0.8106	81.06%
Eye irritation	+	0.9916	99.16%
Skin irritation	-	0.6499	64.99%
Skin corrosion	+	0.5419	54.19%
Ames mutagenesis	-	0.9070	90.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.9335	93.35%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.8875	88.75%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	0.8111	81.11%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	-	0.6930	69.30%
Acute Oral Toxicity (c)	IV	0.6278	62.78%
Estrogen receptor binding	-	0.8551	85.51%
Androgen receptor binding	-	0.8408	84.08%
Thyroid receptor binding	-	0.8339	83.39%
Glucocorticoid receptor binding	-	0.9437	94.37%
Aromatase binding	-	0.9194	91.94%
PPAR gamma	-	0.7460	74.60%
Honey bee toxicity	-	0.9499	94.99%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9168	91.68%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5957	P21589	5'-nucleotidase	8200 nM	IC50	PMID: 24215819
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.74%	95.56%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	86.95%	95.48%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.04%	96.09%

Plants that contains it

• Aesculus turbinata
• Alnus alnobetula
• Argyreia nervosa
• Artocarpus styracifolius
• Capsella bursa-pastoris
• Dorstenia mannii
• Forsythia giraldiana
• Krameria erecta
• Swertia diluta

Cross-Links

• PubChem: 8479
• NPASS: NPC107135
• ChEMBL: CHEMBL1566888
• LOTUS: LTS0267393
• wikiData: Q253746