(5S)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylheptan-3-one

Details

• Internal ID: 5a021158-0933-49d5-9829-5df2e974f0ee
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (5S)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylheptan-3-one
• SMILES (Canonical): C1=CC=C(C=C1)CCC(CC(=O)CCC2=CC=C(C=C2)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)CC[C@@H](CC(=O)CCC2=CC=C(C=C2)O)O
• InChI: InChI=1S/C19H22O3/c20-17-10-6-16(7-11-17)9-13-19(22)14-18(21)12-8-15-4-2-1-3-5-15/h1-7,10-11,18,20-21H,8-9,12-14H2/t18-/m0/s1
• InChI Key: NKSWRYBLSIGGIU-SFHVURJKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.40 g/mol
• Exact Mass: 298.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9916	99.16%
Caco-2	-	0.5450	54.50%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.9222	92.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9164	91.64%
OATP1B3 inhibitior	+	0.9334	93.34%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6720	67.20%
P-glycoprotein inhibitior	-	0.7920	79.20%
P-glycoprotein substrate	-	0.6198	61.98%
CYP3A4 substrate	-	0.5541	55.41%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	+	0.3632	36.32%
CYP3A4 inhibition	-	0.6093	60.93%
CYP2C9 inhibition	-	0.7352	73.52%
CYP2C19 inhibition	+	0.6083	60.83%
CYP2D6 inhibition	-	0.9075	90.75%
CYP1A2 inhibition	-	0.7417	74.17%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.7619	76.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8211	82.11%
Carcinogenicity (trinary)	Non-required	0.6057	60.57%
Eye corrosion	-	0.9841	98.41%
Eye irritation	+	0.5668	56.68%
Skin irritation	-	0.6163	61.63%
Skin corrosion	-	0.9309	93.09%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7013	70.13%
Micronuclear	-	0.8041	80.41%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7890	78.90%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7346	73.46%
Acute Oral Toxicity (c)	III	0.7120	71.20%
Estrogen receptor binding	+	0.8369	83.69%
Androgen receptor binding	+	0.7671	76.71%
Thyroid receptor binding	-	0.6552	65.52%
Glucocorticoid receptor binding	-	0.6862	68.62%
Aromatase binding	-	0.4882	48.82%
PPAR gamma	+	0.7316	73.16%
Honey bee toxicity	-	0.8294	82.94%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9364	93.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.88%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	97.03%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.08%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.77%	99.17%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	90.66%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.78%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.16%	95.50%
CHEMBL2535	P11166	Glucose transporter	83.61%	98.75%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.16%	94.08%
CHEMBL3401	O75469	Pregnane X receptor	81.49%	94.73%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.19%	100.00%
CHEMBL3761	Q9HCG7	Beta-glucosidase	80.09%	99.00%
CHEMBL1255126	O15151	Protein Mdm4	80.04%	90.20%

Plants that contains it

• Curcuma kwangsiensis

Cross-Links

• PubChem: 54577336
• NPASS: NPC252544
• LOTUS: LTS0027129
• wikiData: Q105181012