2-Methoxy-4-[(1R,2S)-1,3-dihydroxy-2-[2-methoxy-4-(3-hydroxypropyl)phenoxy]propyl]phenol

Details

• Internal ID: 767569cf-c256-4c8b-b3c5-32e49238c9c4
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (1R,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propane-1,3-diol
• SMILES (Canonical): COC1=C(C=CC(=C1)CCCO)OC(CO)C(C2=CC(=C(C=C2)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CCCO)O[C@@H](CO)[C@@H](C2=CC(=C(C=C2)O)OC)O
• InChI: InChI=1S/C20H26O7/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/h5-8,10-11,19-24H,3-4,9,12H2,1-2H3/t19-,20+/m0/s1
• InChI Key: DBIKJXXBCAHHMC-VQTJNVASSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.16785316 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• 2-Methoxy-4-[(1R,2S)-1,3-dihydroxy-2-[2-methoxy-4-(3-hydroxypropyl)phenoxy]propyl]phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9350	93.50%
Caco-2	-	0.5162	51.62%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7752	77.52%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8498	84.98%
OATP1B3 inhibitior	+	0.9364	93.64%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4892	48.92%
P-glycoprotein inhibitior	+	0.7151	71.51%
P-glycoprotein substrate	+	0.6010	60.10%
CYP3A4 substrate	+	0.5421	54.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4412	44.12%
CYP3A4 inhibition	-	0.8137	81.37%
CYP2C9 inhibition	-	0.7183	71.83%
CYP2C19 inhibition	-	0.7667	76.67%
CYP2D6 inhibition	-	0.9073	90.73%
CYP1A2 inhibition	+	0.6358	63.58%
CYP2C8 inhibition	+	0.6710	67.10%
CYP inhibitory promiscuity	-	0.7214	72.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.7440	74.40%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8999	89.99%
Skin irritation	-	0.8026	80.26%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3941	39.41%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.6696	66.96%
skin sensitisation	-	0.7408	74.08%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8938	89.38%
Acute Oral Toxicity (c)	III	0.8471	84.71%
Estrogen receptor binding	+	0.8665	86.65%
Androgen receptor binding	+	0.6567	65.67%
Thyroid receptor binding	+	0.7679	76.79%
Glucocorticoid receptor binding	+	0.6177	61.77%
Aromatase binding	-	0.5851	58.51%
PPAR gamma	+	0.5465	54.65%
Honey bee toxicity	-	0.9058	90.58%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.5135	51.35%

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	99.11%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.08%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.99%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.17%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	93.06%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.81%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.05%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.34%	86.92%
CHEMBL2535	P11166	Glucose transporter	89.18%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.05%	91.11%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.01%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.53%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.10%	99.15%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	83.42%	87.16%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.70%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.11%	90.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.00%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.99%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.75%	95.56%

Plants that contains it

• Acer carpinifolium
• Achillea arabica
• Acrisione denticulata
• Alcea rosea
• Alpinia roxburghii
• Archidendron ellipticum
• Baccharis dracunculifolia
• Balanops australiana
• Berberis orthobotrys
• Blumea eriantha
• Bulbinella floribunda
• Caryocar villosum
• Cephalotaxus harringtonii
• Ceriops decandra
• Cipadessa baccifera
• Cleistopholis staudtii
• Cucurbita moschata
• Dalbergia ecastaphyllum
• Davallia perdurans
• Diplazium esculentum
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium sagittatum
• Epimedium wushanense
• Euonymus laxiflorus
• Euonymus tingens
• Euphorbia cornigera
• Euphorbia jolkinii
• Euterpe oleracea
• Galium rubioides
• Glochidion philippicum
• Gonzalezia decurrens
• Helianthus annuus
• Helichrysum lepidissimum
• Helleborus multifidus
• Himalaiella deltoidea
• Hopea utilis
• Hylocomium splendens
• Hypericum revolutum
• Ilex brevicuspis
• Kokoona reflexa
• Leuzea centauroides
• Litsea salicifolia
• Maesa ramentacea
• Magnolia officinalis
• Mesembryanthemum expansum
• Millettia laurentii
• Monodora tenuifolia
• Myoporum platycarpum
• Ocimum gratissimum
• Ocimum tenuiflorum
• Ongokea gore
• Osmorhiza aristata
• Palaquium canaliculatum
• Phlojodicarpus sibiricus
• Physalis sordida
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Psychotria serpens
• Pycnandra acuminata
• Salacia lehmbachii
• Salvia yosgadensis
• Sanicula epipactis
• Senecio heliopsis
• Sideritis brevibracteata
• Sideroxylon cubense
• Solidago petiolaris
• Stipa robusta
• Succisa pratensis
• Tabernaemontana divaricata
• Zaluzania grayana
• Zanthoxylum rhoifolium
• Zygia racemosa

Cross-Links

• PubChem: 13893597
• NPASS: NPC218943
• LOTUS: LTS0176913
• wikiData: Q104974417