1,3-Naphthalenediol

Details

• Internal ID: 24899b74-d42a-4468-8e6f-e228da4e1f68
• Taxonomy: Benzenoids > Naphthalenes > Naphthols and derivatives
• IUPAC Name: naphthalene-1,3-diol
• SMILES (Canonical): C1=CC=C2C(=C1)C=C(C=C2O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C=C(C=C2O)O
• InChI: InChI=1S/C10H8O2/c11-8-5-7-3-1-2-4-9(7)10(12)6-8/h1-6,11-12H
• InChI Key: XOOMNEFVDUTJPP-UHFFFAOYSA-N
• Popularity: 249 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17 g/mol
• Exact Mass: 160.052429494 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 132-86-5
• 1,3-DIHYDROXYNAPHTHALENE
• Naphthalene-1,3-diol
• Naphthoresorcinol
• Naphthoresoucinol
• 3-Hydroxybenzocyclohexadien-1-one
• MFCD00003965
• Naphthoresorcin
• CCRIS 7896
• NSC-115890
• NSC 115890
• AI3-08780
• EINECS 205-079-7
• BRN 2044002
• UNII-5X457YEW8Y
• 5X457YEW8Y
• 4-06-00-06543 (Beilstein Handbook Reference)
• 1,3-Naphthalindiol
• 1-Hydroxy-3-naphthol
• Naphthalenediol-(1,3)
• 2,4-dihydroxynaphthalene
• 1,3-dihydroxy-naphthalene
• D04PMX
• WLN: L66J BQ DQ
• SCHEMBL28681
• NAPHTHORESORCINOL [MI]
• CHEMBL381547
• LCZC2960
• DTXSID8059631
• BDBM23449
• AMY6315
• 1,3-Naphthalenediol (8CI,9CI)
• HY-D0165
• NSC115890
• STL416210
• AKOS005145943
• 6-Methoxypyridine-2-carboxylicacidamide
• s10388
• AC-15068
• DS-14529
• LS-94566
• LS-94592
• SY010964
• CS-0010073
• D0588
• FT-0631769
• 1,3-Dihydroxynaphthalene, >=99%, crystalline
• N-2150
• A806508
• Q27262989
• InChI=1/C10H8O2/c11-8-5-7-3-1-2-4-9(7)10(12)6-8/h1-6,11-12
• 1,3-Dihydroxynaphthalene, for spectrophotometric det. of glucuronic acid according to Tollens, >=97.0%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.9627	96.27%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4654	46.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9339	93.39%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8888	88.88%
P-glycoprotein inhibitior	-	0.9808	98.08%
P-glycoprotein substrate	-	0.9880	98.80%
CYP3A4 substrate	-	0.6668	66.68%
CYP2C9 substrate	-	0.8333	83.33%
CYP2D6 substrate	+	0.3949	39.49%
CYP3A4 inhibition	-	0.6305	63.05%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.7138	71.38%
CYP2D6 inhibition	-	0.8702	87.02%
CYP1A2 inhibition	+	0.9629	96.29%
CYP2C8 inhibition	+	0.4449	44.49%
CYP inhibitory promiscuity	+	0.6431	64.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7145	71.45%
Carcinogenicity (trinary)	Non-required	0.5187	51.87%
Eye corrosion	-	0.9638	96.38%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.7066	70.66%
Skin corrosion	-	0.8885	88.85%
Ames mutagenesis	+	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7813	78.13%
Micronuclear	-	0.6323	63.23%
Hepatotoxicity	+	0.6698	66.98%
skin sensitisation	+	0.8223	82.23%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	-	0.7444	74.44%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6021	60.21%
Acute Oral Toxicity (c)	III	0.7436	74.36%
Estrogen receptor binding	+	0.6053	60.53%
Androgen receptor binding	+	0.5574	55.74%
Thyroid receptor binding	+	0.5222	52.22%
Glucocorticoid receptor binding	-	0.6407	64.07%
Aromatase binding	-	0.7416	74.16%
PPAR gamma	+	0.7450	74.50%
Honey bee toxicity	-	0.9546	95.46%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	+	0.7400	74.00%
Fish aquatic toxicity	+	0.8595	85.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3959	P16083	Quinone reductase 2	3300 nM	IC50	PMID: 21074425

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.42%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.32%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.78%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.34%	99.15%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.11%	96.12%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.24%	94.62%
CHEMBL2535	P11166	Glucose transporter	82.24%	98.75%
CHEMBL2581	P07339	Cathepsin D	81.54%	98.95%

Plants that contains it

• Senna tora

Cross-Links

• PubChem: 8601
• NPASS: NPC202647
• ChEMBL: CHEMBL381547