4-[(2S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(2-methyl-4-oxopyran-3-yl)oxyoxan-3-yl]oxy-2-hydroxy-3-methylbutoxy]furo[3,2-g]chromen-7-one

Details

• Internal ID: a24beaeb-7b4e-4975-802c-ae7c8a9aa6b4
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 4-[(2S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(2-methyl-4-oxopyran-3-yl)oxyoxan-3-yl]oxy-2-hydroxy-3-methylbutoxy]furo[3,2-g]chromen-7-one
• SMILES (Canonical): CC1=C(C(=O)C=CO1)OC2C(C(C(C(O2)CO)O)O)OC(C)(C)C(COC3=C4C=CC(=O)OC4=CC5=C3C=CO5)O
• SMILES (Isomeric): CC1=C(C(=O)C=CO1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)OC(C)(C)[C@H](COC3=C4C=CC(=O)OC4=CC5=C3C=CO5)O
• InChI: InChI=1S/C28H30O13/c1-13-24(16(30)7-9-35-13)40-27-26(23(34)22(33)19(11-29)39-27)41-28(2,3)20(31)12-37-25-14-4-5-21(32)38-18(14)10-17-15(25)6-8-36-17/h4-10,19-20,22-23,26-27,29,31,33-34H,11-12H2,1-3H3/t19-,20+,22-,23+,26-,27+/m1/s1
• InChI Key: BDLJCFOGDWQORY-ACNHYDIVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₀O₁₃
• Molecular Weight: 574.50 g/mol
• Exact Mass: 574.16864101 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.22
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7390	73.90%
Caco-2	-	0.8189	81.89%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6265	62.65%
OATP2B1 inhibitior	-	0.8525	85.25%
OATP1B1 inhibitior	+	0.8779	87.79%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9188	91.88%
P-glycoprotein inhibitior	+	0.6917	69.17%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6685	66.85%
CYP2C9 substrate	-	0.8255	82.55%
CYP2D6 substrate	-	0.8673	86.73%
CYP3A4 inhibition	-	0.9430	94.30%
CYP2C9 inhibition	-	0.9034	90.34%
CYP2C19 inhibition	-	0.8958	89.58%
CYP2D6 inhibition	-	0.9326	93.26%
CYP1A2 inhibition	-	0.7787	77.87%
CYP2C8 inhibition	+	0.5639	56.39%
CYP inhibitory promiscuity	-	0.8839	88.39%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6025	60.25%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9267	92.67%
Skin irritation	-	0.8087	80.87%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9091	90.91%
Micronuclear	-	0.5667	56.67%
Hepatotoxicity	+	0.5908	59.08%
skin sensitisation	-	0.8652	86.52%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.9517	95.17%
Acute Oral Toxicity (c)	III	0.6488	64.88%
Estrogen receptor binding	+	0.8323	83.23%
Androgen receptor binding	+	0.7543	75.43%
Thyroid receptor binding	+	0.5587	55.87%
Glucocorticoid receptor binding	+	0.6384	63.84%
Aromatase binding	+	0.6254	62.54%
PPAR gamma	+	0.7106	71.06%
Honey bee toxicity	-	0.7232	72.32%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9357	93.57%

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	99.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.80%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.50%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.75%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.10%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.66%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.37%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.21%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.97%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.97%	99.17%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	90.18%	93.65%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.07%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.53%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.53%	89.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.46%	100.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.41%	94.03%
CHEMBL4581	P52732	Kinesin-like protein 1	82.57%	93.18%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.56%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.83%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.54%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.51%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.44%	86.92%
CHEMBL220	P22303	Acetylcholinesterase	80.16%	94.45%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.13%	85.94%

Plants that contains it

• Prangos pabularia

Cross-Links

• PubChem: 163083971
• LOTUS: LTS0225239
• wikiData: Q104924371