(2S)-5-hydroxy-6,8-bis[(2-hydroxyphenyl)methyl]-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 34688516-e2fb-49b2-8632-69a2f64c878e
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2S)-5-hydroxy-6,8-bis[(2-hydroxyphenyl)methyl]-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C=C(C(=C2C1=O)O)CC3=CC=CC=C3O)CC4=CC=CC=C4O)C5=CC=CC=C5
• SMILES (Isomeric): C1[C@H](OC2=C(C=C(C(=C2C1=O)O)CC3=CC=CC=C3O)CC4=CC=CC=C4O)C5=CC=CC=C5
• InChI: InChI=1S/C29H24O5/c30-23-12-6-4-10-19(23)14-21-16-22(15-20-11-5-7-13-24(20)31)29-27(28(21)33)25(32)17-26(34-29)18-8-2-1-3-9-18/h1-13,16,26,30-31,33H,14-15,17H2/t26-/m0/s1
• InChI Key: XRWPIFOOLJOTOK-SANMLTNESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₄O₅
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.16237386 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.69
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9652	96.52%
Caco-2	-	0.8602	86.02%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8663	86.63%
OATP2B1 inhibitior	-	0.5769	57.69%
OATP1B1 inhibitior	+	0.9009	90.09%
OATP1B3 inhibitior	+	0.9255	92.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9112	91.12%
P-glycoprotein inhibitior	+	0.7816	78.16%
P-glycoprotein substrate	-	0.8853	88.53%
CYP3A4 substrate	-	0.5095	50.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	-	0.7411	74.11%
CYP2C9 inhibition	+	0.9081	90.81%
CYP2C19 inhibition	+	0.8555	85.55%
CYP2D6 inhibition	-	0.8856	88.56%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.5522	55.22%
CYP inhibitory promiscuity	+	0.5189	51.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.6296	62.96%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.5702	57.02%
Skin irritation	-	0.6339	63.39%
Skin corrosion	-	0.9762	97.62%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8267	82.67%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7396	73.96%
Acute Oral Toxicity (c)	I	0.5715	57.15%
Estrogen receptor binding	+	0.7681	76.81%
Androgen receptor binding	+	0.7057	70.57%
Thyroid receptor binding	+	0.5842	58.42%
Glucocorticoid receptor binding	+	0.6922	69.22%
Aromatase binding	-	0.5776	57.76%
PPAR gamma	+	0.7805	78.05%
Honey bee toxicity	-	0.8370	83.70%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9407	94.07%

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	99.51%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.82%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.95%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.89%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.81%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.26%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.59%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.82%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.82%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.41%	99.23%

Plants that contains it

• Piper sarmentosum

Cross-Links

• PubChem: 163086801
• LOTUS: LTS0140013
• wikiData: Q105340844