(2R)-2-[3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-1,2-dihydronaphthalene-1-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid

Details

• Internal ID: 963d0210-5b44-491d-b255-14cf5b611036
• Taxonomy: Benzenoids > Naphthalenes > Phenylnaphthalenes
• IUPAC Name: (2R)-2-[3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-1,2-dihydronaphthalene-1-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C2C(C(=CC3=C2C(=C(C=C3)O)O)C(=O)OC(CC4=CC(=C(C=C4)O)O)C(=O)O)C5=CC(=C(C=C5)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)C2C(C(=CC3=C2C(=C(C=C3)O)O)C(=O)O[C@H](CC4=CC(=C(C=C4)O)O)C(=O)O)C5=CC(=C(C=C5)O)O)O)O
• InChI: InChI=1S/C36H30O16/c37-20-5-1-15(9-24(20)41)11-27(33(45)46)51-35(49)19-13-17-4-8-23(40)32(44)30(17)31(29(19)18-3-7-22(39)26(43)14-18)36(50)52-28(34(47)48)12-16-2-6-21(38)25(42)10-16/h1-10,13-14,27-29,31,37-44H,11-12H2,(H,45,46)(H,47,48)/t27-,28-,29?,31?/m1/s1
• InChI Key: CLZDRNKNWXDFQT-UNTSIKIQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₀O₁₆
• Molecular Weight: 718.60 g/mol
• Exact Mass: 718.15338487 g/mol
• Topological Polar Surface Area (TPSA): 289.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• BDBM50446663

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9629	96.29%
Caco-2	-	0.9020	90.20%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8069	80.69%
OATP2B1 inhibitior	-	0.7053	70.53%
OATP1B1 inhibitior	+	0.8553	85.53%
OATP1B3 inhibitior	+	0.9279	92.79%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8979	89.79%
P-glycoprotein inhibitior	+	0.7395	73.95%
P-glycoprotein substrate	-	0.7303	73.03%
CYP3A4 substrate	+	0.6001	60.01%
CYP2C9 substrate	-	0.5984	59.84%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.8993	89.93%
CYP2C9 inhibition	+	0.6172	61.72%
CYP2C19 inhibition	-	0.8165	81.65%
CYP2D6 inhibition	-	0.8863	88.63%
CYP1A2 inhibition	-	0.5120	51.20%
CYP2C8 inhibition	+	0.7495	74.95%
CYP inhibitory promiscuity	-	0.6275	62.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8997	89.97%
Carcinogenicity (trinary)	Non-required	0.5372	53.72%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8742	87.42%
Skin irritation	-	0.7084	70.84%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7807	78.07%
Micronuclear	+	0.7618	76.18%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.6355	63.55%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9299	92.99%
Acute Oral Toxicity (c)	III	0.4486	44.86%
Estrogen receptor binding	+	0.7837	78.37%
Androgen receptor binding	+	0.8273	82.73%
Thyroid receptor binding	+	0.5256	52.56%
Glucocorticoid receptor binding	-	0.4644	46.44%
Aromatase binding	-	0.5852	58.52%
PPAR gamma	+	0.6595	65.95%
Honey bee toxicity	-	0.6851	68.51%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4977	P05412	Proto-oncogene c-JUN	1600 nM	IC50	PMID: 18809945

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.64%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.13%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.75%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.47%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.26%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.78%	99.15%
CHEMBL2581	P07339	Cathepsin D	92.30%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.90%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.10%	97.09%
CHEMBL3194	P02766	Transthyretin	85.54%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	84.96%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.90%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.43%	89.67%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.26%	96.38%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.75%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	81.87%	91.19%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.75%	86.92%

Plants that contains it

• Capsicum annuum
• Cucurbita maxima
• Plectranthus amboinicus

Cross-Links

• PubChem: 76324956
• NPASS: NPC471750
• ChEMBL: CHEMBL3113339
• LOTUS: LTS0042755
• wikiData: Q105301151