(2R,2'R,4R,4'R)-4,4'-dihydroxy-3,3',4,4'-tetrahydro-2,2'-binaphthalene-1,1'(2H,2'H)-dione

Details

• Internal ID: 4c2edb8e-e4fa-4778-b086-94ae120fa98e
• Taxonomy: Benzenoids > Tetralins
• IUPAC Name: (2R,4R)-4-hydroxy-2-[(2R,4R)-4-hydroxy-1-oxo-3,4-dihydro-2H-naphthalen-2-yl]-3,4-dihydro-2H-naphthalen-1-one
• SMILES (Canonical): C1C(C(=O)C2=CC=CC=C2C1O)C3CC(C4=CC=CC=C4C3=O)O
• SMILES (Isomeric): C1[C@@H](C(=O)C2=CC=CC=C2[C@@H]1O)[C@H]3C[C@H](C4=CC=CC=C4C3=O)O
• InChI: InChI=1S/C20H18O4/c21-17-9-15(19(23)13-7-3-1-5-11(13)17)16-10-18(22)12-6-2-4-8-14(12)20(16)24/h1-8,15-18,21-22H,9-10H2/t15-,16-,17-,18-/m1/s1
• InChI Key: KXYYQTOKRSUJFQ-BRSBDYLESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.12050905 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.86
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• CHEBI:69515
• Q27137854
• (4RS,4'RS)-dihydroxy-(2RS,2'RS)-binaphthalene-1,1'-dione
• (2R,2'R,4R,4'R)-4,4'-Dihydroxy-2,2'-bitetralin-1,1'-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.6302	63.02%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8991	89.91%
OATP2B1 inhibitior	-	0.7235	72.35%
OATP1B1 inhibitior	+	0.9271	92.71%
OATP1B3 inhibitior	+	0.8937	89.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7644	76.44%
P-glycoprotein inhibitior	-	0.8253	82.53%
P-glycoprotein substrate	-	0.9622	96.22%
CYP3A4 substrate	-	0.5552	55.52%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	-	0.7262	72.62%
CYP3A4 inhibition	-	0.8622	86.22%
CYP2C9 inhibition	+	0.6294	62.94%
CYP2C19 inhibition	-	0.6462	64.62%
CYP2D6 inhibition	-	0.7113	71.13%
CYP1A2 inhibition	+	0.6195	61.95%
CYP2C8 inhibition	-	0.8782	87.82%
CYP inhibitory promiscuity	-	0.8600	86.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8156	81.56%
Carcinogenicity (trinary)	Non-required	0.5752	57.52%
Eye corrosion	-	0.9947	99.47%
Eye irritation	-	0.5829	58.29%
Skin irritation	-	0.5505	55.05%
Skin corrosion	-	0.9756	97.56%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7256	72.56%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	+	0.7803	78.03%
skin sensitisation	-	0.8236	82.36%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.6557	65.57%
Acute Oral Toxicity (c)	III	0.6224	62.24%
Estrogen receptor binding	+	0.8314	83.14%
Androgen receptor binding	+	0.6909	69.09%
Thyroid receptor binding	-	0.5815	58.15%
Glucocorticoid receptor binding	+	0.5563	55.63%
Aromatase binding	+	0.5496	54.96%
PPAR gamma	+	0.5455	54.55%
Honey bee toxicity	-	0.8951	89.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9830	98.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.40%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.00%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.60%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.82%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.73%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.01%	96.09%
CHEMBL308	P06493	Cyclin-dependent kinase 1	83.93%	91.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.75%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.11%	89.00%

Plants that contains it

• Rubia yunnanensis

Cross-Links

• PubChem: 56600471
• NPASS: NPC265736
• LOTUS: LTS0226176
• wikiData: Q27137854