[(2R)-3-hydroxy-3-methyl-1-(7-oxofuro[3,2-g]chromen-9-yl)oxybutan-2-yl] (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate

Details

• Internal ID: 162e56c9-15db-407e-b63e-b083fa46f380
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: [(2R)-3-hydroxy-3-methyl-1-(7-oxofuro[3,2-g]chromen-9-yl)oxybutan-2-yl] (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate
• SMILES (Canonical): CC(C)(C(COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)OC(=O)C4(CC(C(C(C4)OC(=O)C=CC5=CC(=C(C=C5)O)OC)O)O)O)O
• SMILES (Isomeric): CC(C)([C@@H](COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)OC(=O)[C@@]4(C[C@H]([C@H]([C@@H](C4)OC(=O)/C=C/C5=CC(=C(C=C5)O)OC)O)O)O)O
• InChI: InChI=1S/C33H34O14/c1-32(2,40)24(16-44-30-28-19(10-11-43-28)13-18-6-9-26(37)47-29(18)30)46-31(39)33(41)14-21(35)27(38)23(15-33)45-25(36)8-5-17-4-7-20(34)22(12-17)42-3/h4-13,21,23-24,27,34-35,38,40-41H,14-16H2,1-3H3/b8-5+/t21-,23-,24-,27-,33+/m1/s1
• InChI Key: OLPWNMQCTIHXKY-YTLVSIORSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₄O₁₄
• Molecular Weight: 654.60 g/mol
• Exact Mass: 654.19485575 g/mol
• Topological Polar Surface Area (TPSA): 212.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8809	88.09%
Caco-2	-	0.8744	87.44%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6595	65.95%
OATP2B1 inhibitior	+	0.5622	56.22%
OATP1B1 inhibitior	+	0.8873	88.73%
OATP1B3 inhibitior	+	0.9277	92.77%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8919	89.19%
P-glycoprotein inhibitior	+	0.7306	73.06%
P-glycoprotein substrate	+	0.6693	66.93%
CYP3A4 substrate	+	0.6866	68.66%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8517	85.17%
CYP3A4 inhibition	-	0.8760	87.60%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.8698	86.98%
CYP2D6 inhibition	-	0.8720	87.20%
CYP1A2 inhibition	-	0.7522	75.22%
CYP2C8 inhibition	+	0.8016	80.16%
CYP inhibitory promiscuity	-	0.8629	86.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5862	58.62%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.7862	78.62%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7492	74.92%
Micronuclear	-	0.5126	51.26%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8270	82.70%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.9482	94.82%
Acute Oral Toxicity (c)	III	0.4595	45.95%
Estrogen receptor binding	+	0.8089	80.89%
Androgen receptor binding	+	0.7933	79.33%
Thyroid receptor binding	+	0.6028	60.28%
Glucocorticoid receptor binding	+	0.7964	79.64%
Aromatase binding	+	0.6256	62.56%
PPAR gamma	+	0.7311	73.11%
Honey bee toxicity	-	0.7331	73.31%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9852	98.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.82%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.36%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.46%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.90%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.66%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	93.15%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.07%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.75%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.16%	96.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	90.43%	85.31%
CHEMBL4040	P28482	MAP kinase ERK2	90.09%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.72%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.72%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.44%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.33%	92.62%
CHEMBL2581	P07339	Cathepsin D	89.26%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.91%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	88.83%	94.73%
CHEMBL2535	P11166	Glucose transporter	88.40%	98.75%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.60%	97.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.30%	91.07%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.93%	99.15%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.79%	96.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.69%	89.62%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	85.95%	98.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.97%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.13%	95.83%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.69%	100.00%
CHEMBL4208	P20618	Proteasome component C5	82.61%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.23%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.18%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.77%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.05%	90.71%

Plants that contains it

• Heracleum candicans

Cross-Links

• PubChem: 101502035
• LOTUS: LTS0012261
• wikiData: Q105194091