[(2S,3R)-3-[(2R)-2-hydroxy-4-(4-hydroxyphenyl)butyl]oxiran-2-yl]-(4-hydroxyphenyl)methanone

Details

• Internal ID: 4431eac2-f9b7-426a-8832-33b3337787ac
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: [(2S,3R)-3-[(2R)-2-hydroxy-4-(4-hydroxyphenyl)butyl]oxiran-2-yl]-(4-hydroxyphenyl)methanone
• InChI: InChI=1S/C19H20O5/c20-14-6-1-12(2-7-14)3-8-16(22)11-17-19(24-17)18(23)13-4-9-15(21)10-5-13/h1-2,4-7,9-10,16-17,19-22H,3,8,11H2/t16-,17-,19+/m1/s1
• InChI Key: SFLXZEYRHVXOSA-LMMKCTJWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.13107373 g/mol
• Topological Polar Surface Area (TPSA): 90.30 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9548	95.48%
Caco-2	+	0.5536	55.36%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8141	81.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8996	89.96%
OATP1B3 inhibitior	+	0.8945	89.45%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8635	86.35%
P-glycoprotein inhibitior	-	0.7208	72.08%
P-glycoprotein substrate	-	0.6699	66.99%
CYP3A4 substrate	-	0.5217	52.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7286	72.86%
CYP3A4 inhibition	-	0.6451	64.51%
CYP2C9 inhibition	-	0.8005	80.05%
CYP2C19 inhibition	-	0.7603	76.03%
CYP2D6 inhibition	-	0.9180	91.80%
CYP1A2 inhibition	-	0.7531	75.31%
CYP2C8 inhibition	+	0.5506	55.06%
CYP inhibitory promiscuity	-	0.7860	78.60%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4959	49.59%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.8004	80.04%
Skin irritation	-	0.5970	59.70%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4893	48.93%
Micronuclear	-	0.5423	54.23%
Hepatotoxicity	-	0.5468	54.68%
skin sensitisation	-	0.6989	69.89%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7988	79.88%
Acute Oral Toxicity (c)	III	0.7342	73.42%
Estrogen receptor binding	+	0.8973	89.73%
Androgen receptor binding	+	0.7868	78.68%
Thyroid receptor binding	+	0.5951	59.51%
Glucocorticoid receptor binding	+	0.7374	73.74%
Aromatase binding	+	0.6129	61.29%
PPAR gamma	+	0.7484	74.84%
Honey bee toxicity	-	0.8222	82.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.8473	84.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	92.56%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.58%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.39%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.06%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.86%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.16%	95.89%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	87.62%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.56%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.27%	86.33%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.42%	85.00%
CHEMBL233	P35372	Mu opioid receptor	84.36%	97.93%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.67%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.13%	97.09%
CHEMBL2514	O95665	Neurotensin receptor 2	81.68%	100.00%

Plants that contains it

• Viscum coloratum

Cross-Links

• PubChem: 162989758
• LOTUS: LTS0091318
• wikiData: Q105251850