Tocris-1610

Details

• Internal ID: 480e0640-77ad-40ab-9ab3-5c47b00915b8
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (Z)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
• SMILES (Canonical): CC1=C(C(=C(C(=C1O)C(=O)C)O)CC2=C(C(=C3C(=C2O)C=CC(O3)(C)C)C(=O)C=CC4=CC=CC=C4)O)O
• SMILES (Isomeric): CC1=C(C(=C(C(=C1O)C(=O)C)O)CC2=C(C(=C3C(=C2O)C=CC(O3)(C)C)C(=O)/C=C\C4=CC=CC=C4)O)O
• InChI: InChI=1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10-
• InChI Key: DEZFNHCVIZBHBI-KHPPLWFESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₈O₈
• Molecular Weight: 516.50 g/mol
• Exact Mass: 516.17841785 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.40
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• Lopac-R-5648
• SCHEMBL2524109
• CHEMBL1330502
• NCGC00015896-01
• NCGC00025228-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9633	96.33%
Caco-2	-	0.8155	81.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7080	70.80%
OATP2B1 inhibitior	+	0.5684	56.84%
OATP1B1 inhibitior	+	0.7262	72.62%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9771	97.71%
P-glycoprotein inhibitior	+	0.7288	72.88%
P-glycoprotein substrate	-	0.6377	63.77%
CYP3A4 substrate	+	0.6034	60.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8280	82.80%
CYP3A4 inhibition	-	0.7030	70.30%
CYP2C9 inhibition	+	0.6898	68.98%
CYP2C19 inhibition	-	0.6109	61.09%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.7303	73.03%
CYP inhibitory promiscuity	+	0.5728	57.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6482	64.82%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.7428	74.28%
Skin irritation	-	0.7567	75.67%
Skin corrosion	-	0.9164	91.64%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8916	89.16%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.7344	73.44%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8476	84.76%
Acute Oral Toxicity (c)	III	0.6144	61.44%
Estrogen receptor binding	+	0.9125	91.25%
Androgen receptor binding	+	0.7671	76.71%
Thyroid receptor binding	+	0.6460	64.60%
Glucocorticoid receptor binding	+	0.8223	82.23%
Aromatase binding	+	0.6147	61.47%
PPAR gamma	+	0.8165	81.65%
Honey bee toxicity	-	0.8629	86.29%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5251	52.51%
Fish aquatic toxicity	+	0.9870	98.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	39810.7 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM	Potency	via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	31622.78 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	1995.3 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	631 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 1000 nM; 12589.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	19952.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	794.3 nM; 794.3 nM; 794.3 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	14125.4 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.77%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.49%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.94%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.40%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.12%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.79%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.24%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.53%	90.00%
CHEMBL5028	O14672	ADAM10	83.00%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.38%	93.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.37%	89.67%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.27%	90.93%

Plants that contains it

• Aloe vera
• Chamaecrista mimosoides
• Mallotus philippensis
• Millettia pachycarpa
• Rhamnus davurica
• Rheum officinale
• Rumex dentatus
• Rumex patientia
• Senna alexandrina
• Senna occidentalis
• Senna tora

Cross-Links

• PubChem: 6603986
• NPASS: NPC278175
• ChEMBL: CHEMBL1330502