(1R,2S)-1-(3-Methoxy-4-hydroxyphenyl)-2-[2-methoxy-4-[(E)-3-hydroxy-1-propenyl]phenoxy]-1,3-propanediol

Details

• Internal ID: 5984dd37-b345-4fe2-9179-820fab760d2e
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (1R,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]propane-1,3-diol
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CCO)OC(CO)C(C2=CC(=C(C=C2)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/CO)O[C@@H](CO)[C@@H](C2=CC(=C(C=C2)O)OC)O
• InChI: InChI=1S/C20H24O7/c1-25-17-11-14(6-7-15(17)23)20(24)19(12-22)27-16-8-5-13(4-3-9-21)10-18(16)26-2/h3-8,10-11,19-24H,9,12H2,1-2H3/b4-3+/t19-,20+/m0/s1
• InChI Key: FYEZJIXULOZDRT-YIYNPQHWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.15220310 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

• CHEMBL1761713
• 890317-92-7
• (+)-erythro-Guaiacylglycerol beta-coniferyl ether
• (1R,2S)-1-(3-Methoxy-4-hydroxyphenyl)-2-[2-methoxy-4-[(E)-3-hydroxy-1-propenyl]phenoxy]-1,3-propanediol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9392	93.92%
Caco-2	+	0.4935	49.35%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6830	68.30%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.8663	86.63%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	+	0.6825	68.25%
P-glycoprotein inhibitior	+	0.7440	74.40%
P-glycoprotein substrate	-	0.7112	71.12%
CYP3A4 substrate	-	0.5211	52.11%
CYP2C9 substrate	-	0.5976	59.76%
CYP2D6 substrate	-	0.6936	69.36%
CYP3A4 inhibition	-	0.5714	57.14%
CYP2C9 inhibition	-	0.7229	72.29%
CYP2C19 inhibition	-	0.5629	56.29%
CYP2D6 inhibition	-	0.8677	86.77%
CYP1A2 inhibition	+	0.6923	69.23%
CYP2C8 inhibition	-	0.6364	63.64%
CYP inhibitory promiscuity	+	0.6309	63.09%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8650	86.50%
Carcinogenicity (trinary)	Non-required	0.7502	75.02%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8725	87.25%
Skin irritation	-	0.8504	85.04%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4266	42.66%
Micronuclear	-	0.5841	58.41%
Hepatotoxicity	-	0.6321	63.21%
skin sensitisation	-	0.5630	56.30%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.8866	88.66%
Acute Oral Toxicity (c)	III	0.7796	77.96%
Estrogen receptor binding	+	0.7606	76.06%
Androgen receptor binding	+	0.6669	66.69%
Thyroid receptor binding	+	0.7327	73.27%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	-	0.4935	49.35%
PPAR gamma	-	0.5204	52.04%
Honey bee toxicity	-	0.8955	89.55%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8633	86.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.79%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.22%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.71%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.70%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.56%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.72%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.02%	99.17%
CHEMBL4208	P20618	Proteasome component C5	88.50%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.34%	99.15%
CHEMBL1255126	O15151	Protein Mdm4	86.93%	90.20%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.76%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.14%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.93%	89.00%
CHEMBL3194	P02766	Transthyretin	84.50%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.96%	96.12%
CHEMBL2535	P11166	Glucose transporter	80.76%	98.75%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.10%	90.24%

Plants that contains it

• Achillea arabica
• Acrisione denticulata
• Anastatica hierochuntica
• Archidendron ellipticum
• Baccharis dracunculifolia
• Berberis orthobotrys
• Blumea eriantha
• Broussonetia papyrifera
• Bulbinella floribunda
• Caryocar villosum
• Cephalotaxus harringtonii
• Ceriops decandra
• Cipadessa baccifera
• Cucurbita moschata
• Dalbergia ecastaphyllum
• Diplazium esculentum
• Echinacea purpurea
• Ehretia matthewii
• Equisetum ramosissimum subsp. debile
• Euonymus alatus
• Euonymus laxiflorus
• Euphorbia jolkinii
• Glochidion philippicum
• Himalaiella deltoidea
• Ilex brevicuspis
• Myoporum platycarpum
• Ocimum gratissimum
• Ongokea gore
• Palaquium canaliculatum
• Phlojodicarpus sibiricus
• Physalis sordida
• Sanicula epipactis
• Senecio heliopsis
• Solidago petiolaris
• Tabernaemontana divaricata
• Zaluzania grayana
• Zanthoxylum rhoifolium
• Zygia racemosa

Cross-Links

• PubChem: 14274760
• NPASS: NPC147821
• LOTUS: LTS0217589
• wikiData: Q105004446