4-[(3R,5R)-3,5-dihydroxy-7-(4-hydroxyphenyl)heptyl]benzene-1,2-diol

Details

• Internal ID: 1d014e4e-55df-4aeb-b932-041c13beb888
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 4-[(3R,5R)-3,5-dihydroxy-7-(4-hydroxyphenyl)heptyl]benzene-1,2-diol
• SMILES (Canonical): C1=CC(=CC=C1CCC(CC(CCC2=CC(=C(C=C2)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CC[C@H](C[C@@H](CCC2=CC(=C(C=C2)O)O)O)O)O
• InChI: InChI=1S/C19H24O5/c20-15-6-1-13(2-7-15)3-8-16(21)12-17(22)9-4-14-5-10-18(23)19(24)11-14/h1-2,5-7,10-11,16-17,20-24H,3-4,8-9,12H2/t16-,17-/m1/s1
• InChI Key: XLTITIJKWVRJMS-IAGOWNOFSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.16237386 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• 408324-00-5
• 4-[(3R,5R)-3,5-dihydroxy-7-(4-hydroxyphenyl)heptyl]benzene-1,2-diol
• CHEMBL443638
• 4-[3,5-Dihydroxy-7-(4-hydroxy-phenyl)-heptyl]-benzene-1,2-diol
• AKOS040761073
• 1,2-benzenediol, 4-[(3R,5R)-3,5-dihydroxy-7-(4-hydroxyphenyl)heptyl]-
• 2-Hydroxy-[4,4'-((3R,5R)-3,5-dihydroxyheptane-1,7-diyl)bisphenol]
• rel-4-[(3R,5R)-3,5-dihydroxy-7-(4-hydroxyphenyl)heptyl]benzene-1,2-diol
• InChI=1/C19H24O5/c20-15-6-1-13(2-7-15)3-8-16(21)12-17(22)9-4-14-5-10-18(23)19(24)11-14/h1-2,5-7,10-11,16-17,20-24H,3-4,8-9,12H2/t16-,17-/m1/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8082	80.82%
Caco-2	-	0.6814	68.14%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8020	80.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9349	93.49%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6609	66.09%
P-glycoprotein inhibitior	-	0.7475	74.75%
P-glycoprotein substrate	-	0.6782	67.82%
CYP3A4 substrate	-	0.6033	60.33%
CYP2C9 substrate	-	0.8120	81.20%
CYP2D6 substrate	+	0.4045	40.45%
CYP3A4 inhibition	-	0.7401	74.01%
CYP2C9 inhibition	-	0.7569	75.69%
CYP2C19 inhibition	-	0.8072	80.72%
CYP2D6 inhibition	-	0.8836	88.36%
CYP1A2 inhibition	-	0.6412	64.12%
CYP2C8 inhibition	-	0.7118	71.18%
CYP inhibitory promiscuity	-	0.8492	84.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6621	66.21%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.5581	55.81%
Skin irritation	-	0.5945	59.45%
Skin corrosion	-	0.8221	82.21%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7456	74.56%
Micronuclear	-	0.6741	67.41%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	+	0.5112	51.12%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8081	80.81%
Acute Oral Toxicity (c)	III	0.7845	78.45%
Estrogen receptor binding	+	0.8946	89.46%
Androgen receptor binding	+	0.8503	85.03%
Thyroid receptor binding	+	0.6677	66.77%
Glucocorticoid receptor binding	+	0.6018	60.18%
Aromatase binding	+	0.5541	55.41%
PPAR gamma	+	0.7892	78.92%
Honey bee toxicity	-	0.7445	74.45%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9558	95.58%

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	98.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.60%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	94.24%	98.35%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	90.85%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.67%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.26%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.81%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.14%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	84.49%	91.49%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.23%	94.62%
CHEMBL3194	P02766	Transthyretin	83.56%	90.71%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	83.38%	97.23%
CHEMBL2535	P11166	Glucose transporter	82.58%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.06%	90.71%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.12%	85.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.84%	96.95%
CHEMBL236	P41143	Delta opioid receptor	80.45%	99.35%

Plants that contains it

• Anthriscus sylvestris
• Curcuma comosa
• Curcuma kwangsiensis
• Tacca chantrieri

Cross-Links

• PubChem: 636849
• NPASS: NPC179002
• ChEMBL: CHEMBL443638
• LOTUS: LTS0274056
• wikiData: Q105330373