7-Amino-4-hydroxy-2-naphthalenesulfonic acid

Details

• Internal ID: d490ebd3-5955-4cdb-bac3-6f0cd1dc7aeb
• Taxonomy: Benzenoids > Naphthalenes > Naphthalene sulfonic acids and derivatives > Naphthalene sulfonates > 2-naphthalene sulfonates
• IUPAC Name: 7-amino-4-hydroxynaphthalene-2-sulfonic acid
• SMILES (Canonical): C1=CC2=C(C=C(C=C2C=C1N)S(=O)(=O)O)O
• SMILES (Isomeric): C1=CC2=C(C=C(C=C2C=C1N)S(=O)(=O)O)O
• InChI: InChI=1S/C10H9NO4S/c11-7-1-2-9-6(3-7)4-8(5-10(9)12)16(13,14)15/h1-5,12H,11H2,(H,13,14,15)
• InChI Key: KYARBIJYVGJZLB-UHFFFAOYSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₉NO₄S
• Molecular Weight: 239.25 g/mol
• Exact Mass: 239.02522894 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 7-AMINO-4-HYDROXY-2-NAPHTHALENESULFONIC ACID
• 7-amino-4-hydroxynaphthalene-2-sulfonic acid
• J acid
• Isogamma acid
• I acid
• 2-Amino-5-naphthol-7-sulfonic Acid
• 2-Naphthalenesulfonic acid, 7-amino-4-hydroxy-
• Kyselina I
• Kyselina I [Czech]
• Aminonaphthol sulfonic acid J
• 6-Amino-1-naphthol-3-sulfonic acid
• CCRIS 8989
• 7-Amino-4-hydroxynaphthalene-2-sulphonic acid
• EINECS 201-718-9
• NSC 31510
• Kyselina 2-amino-5-naftol-7-sulfonova
• BRN 2217192
• MLS002638012
• 9A1IU1C93L
• CHEMBL220259
• DTXSID7026520
• 1-Hydroxy-6-amino-3-naphthalenesulfonic acid
• CHEBI:87316
• Kyselina 2-amino-5-naftol-7-sulfonova [Czech]
• Kyselina 6-amino-1-naftol-3-sulfonova [Czech]
• NSC-7556
• NSC-8631
• NSC-31510
• Kyselina 6-amino-1-naftol-3-sulfonova
• 7-amino-4-hydroxy-naphthalene-2-sulfonic acid
• EC 201-718-9
• DTXCID206520
• WLN: L66J BQ DSWQ HZ
• CAS-87-02-5
• J-Saure
• D00SSW
• cid_6868
• UNII-9A1IU1C93L
• J Acid Urea, Disodium Salt
• 3-amino-6-sulfo-8-naphthol
• 6-amino-3-sulfo-1-naphthol
• SCHEMBL154124
• NSC7556
• NSC8631
• KYARBIJYVGJZLB-UHFFFAOYSA-N
• HMS3085K07
• NSC31510
• Tox21_202232
• Tox21_303310
• 3-amino-8-naphthol-6-sulfonic acid
• BDBM50206424
• AKOS015854951
• NCGC00249193-01
• NCGC00257232-01
• NCGC00259781-01
• 7-amino-4-hydroxynaphthalen-2-sulfonsyre
• AS-17223
• LS-94893
• PD183075
• SMR001547516
• 7-amino-4-hydroxynaphthalene-2-sulfonicacid
• A0370
• CS-0187248
• FT-0611181
• 1-HYDROXY-3-SULFO-6-AMINONAPHTHALENE
• 1-hydroxy-6-aminonaphthalene-3-sulphonic acid
• 2-amino-5-hydroxynaphthalene-7-sulfonic acid
• 3-AMINO-8-HYDROXY-6-SULFONAPHTHALENE
• 6-AMINO-1-HYDROXY-3-SULFONAPHTHALENE
• 6-amino-1-hydroxynaphthalene-3-sulfonic acid
• 7-amino-4-hydroxy-2-naphthalenesulphonic acid
• 1-NAPHTHOL-3-SULFONIC ACID, 6-AMINO-
• 7-Amino-4-hydroxy- 2-naphthalenesulfonic acid
• H11790
• * 7-Amino-4-hydroxy-2-naphthalenesulfonic acid
• A915651
• Q259271
• W-104047
• 2-AMINO-5-HYDROXY-7-NAPHTHALENESULFONIC ACID
• 3-AMINO-8-HYDROXY-6-NAPHTHALENESULFONIC ACID
• 6-AMINO-1-HYDROXY-3-NAPHTHALENESULFONIC ACID
• 7-Amino-4-hydroxy-2-naphthalenesulfonic acid, technical, >=90% (T)
• 6-Amino-1-naphthol-3-sulfonic acid;2-Amino-5-naphthol-7-sulfonic acid; 7-Amino-4-hydroxy-2-naphthalene sulphonic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8747	87.47%
Caco-2	+	0.6025	60.25%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Plasma membrane	0.5127	51.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9717	97.17%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9281	92.81%
P-glycoprotein inhibitior	-	0.9670	96.70%
P-glycoprotein substrate	-	0.8517	85.17%
CYP3A4 substrate	-	0.7061	70.61%
CYP2C9 substrate	+	0.6091	60.91%
CYP2D6 substrate	-	0.6703	67.03%
CYP3A4 inhibition	-	0.9077	90.77%
CYP2C9 inhibition	+	0.7242	72.42%
CYP2C19 inhibition	+	0.6893	68.93%
CYP2D6 inhibition	-	0.9436	94.36%
CYP1A2 inhibition	-	0.6780	67.80%
CYP2C8 inhibition	-	0.9329	93.29%
CYP inhibitory promiscuity	-	0.8982	89.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	+	0.8462	84.62%
Carcinogenicity (trinary)	Non-required	0.6017	60.17%
Eye corrosion	+	0.5478	54.78%
Eye irritation	+	0.9012	90.12%
Skin irritation	-	0.7798	77.98%
Skin corrosion	+	0.7948	79.48%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8132	81.32%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.9241	92.41%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.7334	73.34%
Acute Oral Toxicity (c)	IV	0.6189	61.89%
Estrogen receptor binding	-	0.7591	75.91%
Androgen receptor binding	-	0.6312	63.12%
Thyroid receptor binding	-	0.7378	73.78%
Glucocorticoid receptor binding	-	0.6210	62.10%
Aromatase binding	+	0.5641	56.41%
PPAR gamma	-	0.4838	48.38%
Honey bee toxicity	-	0.8149	81.49%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9871	98.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	3430 nM	IC50	via CMAUP
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	1040 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.03%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.43%	91.11%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	89.53%	95.48%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.17%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.22%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.95%	99.15%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.82%	94.42%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.50%	80.78%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.08%	93.03%

Plants that contains it

• Vitis vinifera

Cross-Links

• PubChem: 6868
• NPASS: NPC322283
• ChEMBL: CHEMBL220259