Pierreione A

Details

• Internal ID: 1ab08bf8-1d9d-4f31-8b68-9d04b305c7e8
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 7-[4-[(2R)-2,3-dihydroxy-3-methylbutoxy]-3-methoxyphenyl]-5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-6-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C3C(=C2OC)C(=O)C(=CO3)C4=CC(=C(C=C4)OCC(C(C)(C)O)O)OC)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C3C(=C2OC)C(=O)C(=CO3)C4=CC(=C(C=C4)OC[C@H](C(C)(C)O)O)OC)C
• InChI: InChI=1S/C27H30O8/c1-26(2)10-9-16-19(35-26)12-21-23(25(16)32-6)24(29)17(13-33-21)15-7-8-18(20(11-15)31-5)34-14-22(28)27(3,4)30/h7-13,22,28,30H,14H2,1-6H3/t22-/m1/s1
• InChI Key: XYVIHRJUIIUQSN-JOCHJYFZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₈
• Molecular Weight: 482.50 g/mol
• Exact Mass: 482.19406791 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.17
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• CHEBI:68047
• CHEMBL1773672
• DTXSID601104744
• Q27136543
• 1292766-20-1
• 2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 7-[4-[(2R)-2,3-dihydroxy-3-methylbutoxy]-3-methoxyphenyl]-5-methoxy-2,2-dimethyl-
• 3',5-dimethoxy-4'-(2R,3-dihydroxy-3-methylbutoxyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone
• 7-(4-{[(2R)-2,3-dihydroxy-3-methylbutyl]oxy}-3-methoxyphenyl)-5-methoxy-2,2-dimethyl-2H,6H-pyrano[3,2-g]chromen-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.6232	62.32%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7652	76.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9189	91.89%
OATP1B3 inhibitior	+	0.8954	89.54%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9296	92.96%
P-glycoprotein inhibitior	+	0.8327	83.27%
P-glycoprotein substrate	+	0.5337	53.37%
CYP3A4 substrate	+	0.6715	67.15%
CYP2C9 substrate	-	0.8207	82.07%
CYP2D6 substrate	-	0.8050	80.50%
CYP3A4 inhibition	-	0.8424	84.24%
CYP2C9 inhibition	-	0.8597	85.97%
CYP2C19 inhibition	-	0.6672	66.72%
CYP2D6 inhibition	-	0.8711	87.11%
CYP1A2 inhibition	-	0.6304	63.04%
CYP2C8 inhibition	+	0.7697	76.97%
CYP inhibitory promiscuity	-	0.8277	82.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6647	66.47%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9137	91.37%
Skin irritation	-	0.8075	80.75%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8085	80.85%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.5926	59.26%
skin sensitisation	-	0.8302	83.02%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8124	81.24%
Acute Oral Toxicity (c)	III	0.6183	61.83%
Estrogen receptor binding	+	0.8326	83.26%
Androgen receptor binding	+	0.7576	75.76%
Thyroid receptor binding	+	0.7545	75.45%
Glucocorticoid receptor binding	+	0.8581	85.81%
Aromatase binding	+	0.6867	68.67%
PPAR gamma	+	0.8221	82.21%
Honey bee toxicity	-	0.7761	77.61%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9451	94.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4302	P08183	P-glycoprotein 1	99.44%	92.98%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.05%	85.14%
CHEMBL2581	P07339	Cathepsin D	98.56%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.09%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.59%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.34%	96.09%
CHEMBL5747	Q92793	CREB-binding protein	94.26%	95.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.09%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.06%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.90%	99.17%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.30%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	88.15%	93.31%
CHEMBL1937	Q92769	Histone deacetylase 2	88.03%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.03%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.03%	95.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.67%	95.78%
CHEMBL4208	P20618	Proteasome component C5	85.58%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.32%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.58%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.32%	100.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.49%	95.53%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.13%	89.50%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.91%	96.67%
CHEMBL4040	P28482	MAP kinase ERK2	81.86%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.51%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.81%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.03%	96.00%

Plants that contains it

• Antheroporum pierrei

Cross-Links

• PubChem: 52951513
• LOTUS: LTS0214226
• wikiData: Q27136543