(5S,6S)-5-(3,5-dihydroxyphenyl)-6-(4-hydroxyphenyl)-3-[(E)-2-(4-hydroxyphenyl)ethenyl]cyclohept-2-en-1-one

Details

• Internal ID: a127f372-b1d7-417f-bb7e-af1284276d31
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (5S,6S)-5-(3,5-dihydroxyphenyl)-6-(4-hydroxyphenyl)-3-[(E)-2-(4-hydroxyphenyl)ethenyl]cyclohept-2-en-1-one
• InChI: InChI=1S/C27H24O5/c28-21-7-3-17(4-8-21)1-2-18-11-23(30)16-27(19-5-9-22(29)10-6-19)26(12-18)20-13-24(31)15-25(32)14-20/h1-11,13-15,26-29,31-32H,12,16H2/b2-1+/t26-,27-/m1/s1
• InChI Key: BSKGJESYXYEJPI-IUJWURMNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₅
• Molecular Weight: 428.50 g/mol
• Exact Mass: 428.16237386 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 5.38
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.7675	76.75%
Blood Brain Barrier	-	0.7379	73.79%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8049	80.49%
OATP2B1 inhibitior	-	0.7254	72.54%
OATP1B1 inhibitior	+	0.8724	87.24%
OATP1B3 inhibitior	+	0.8963	89.63%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8338	83.38%
BSEP inhibitior	+	0.9101	91.01%
P-glycoprotein inhibitior	-	0.5153	51.53%
P-glycoprotein substrate	-	0.9106	91.06%
CYP3A4 substrate	-	0.5317	53.17%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.8222	82.22%
CYP3A4 inhibition	+	0.7476	74.76%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.6233	62.33%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	+	0.5779	57.79%
CYP2C8 inhibition	+	0.5535	55.35%
CYP inhibitory promiscuity	+	0.7795	77.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7385	73.85%
Carcinogenicity (trinary)	Non-required	0.6141	61.41%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.6680	66.80%
Skin irritation	-	0.6968	69.68%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8319	83.19%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5519	55.19%
skin sensitisation	-	0.5421	54.21%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5821	58.21%
Acute Oral Toxicity (c)	III	0.5957	59.57%
Estrogen receptor binding	+	0.7586	75.86%
Androgen receptor binding	+	0.8862	88.62%
Thyroid receptor binding	+	0.5985	59.85%
Glucocorticoid receptor binding	+	0.7382	73.82%
Aromatase binding	-	0.5106	51.06%
PPAR gamma	+	0.8621	86.21%
Honey bee toxicity	-	0.8792	87.92%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9968	99.68%

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	98.38%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.72%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.32%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.03%	95.56%
CHEMBL3194	P02766	Transthyretin	90.57%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.93%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.92%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.75%	93.99%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.78%	90.71%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.27%	85.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.68%	96.09%
CHEMBL4208	P20618	Proteasome component C5	82.70%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.93%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.23%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.96%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162962034
• LOTUS: LTS0209228
• wikiData: Q104945274