(+)-8-Methoxyisolariciresinol

Details

• Internal ID: 55ff631f-9638-44d1-9174-e17a79433e3d
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans > 9,9p-dihydroxyaryltetralin lignans
• IUPAC Name: (6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol
• SMILES (Canonical): COC1=C(C(=C2C(C(C(CC2=C1)CO)CO)C3=CC(=C(C=C3)O)OC)OC)O
• SMILES (Isomeric): COC1=C(C(=C2[C@@H]([C@H]([C@@H](CC2=C1)CO)CO)C3=CC(=C(C=C3)O)OC)OC)O
• InChI: InChI=1S/C21H26O7/c1-26-16-7-11(4-5-15(16)24)18-14(10-23)13(9-22)6-12-8-17(27-2)20(25)21(28-3)19(12)18/h4-5,7-8,13-14,18,22-25H,6,9-10H2,1-3H3/t13-,14-,18+/m0/s1
• InChI Key: ZPRAJLPWRSLALC-SUNYJGFJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₇
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.16785316 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• CHEMBL508302
• 136082-41-2
• (6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol
• ZPRAJLPWRSLALC-SUNYJGFJSA-N
• BDBM50242209
• AKOS032962750
• (1S)-1alpha-(4-Hydroxy-3-methoxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2beta,3alpha-dimethanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9735	97.35%
Caco-2	+	0.5931	59.31%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8175	81.75%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4775	47.75%
P-glycoprotein inhibitior	-	0.6269	62.69%
P-glycoprotein substrate	-	0.7744	77.44%
CYP3A4 substrate	+	0.5219	52.19%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.4943	49.43%
CYP3A4 inhibition	-	0.5839	58.39%
CYP2C9 inhibition	-	0.5614	56.14%
CYP2C19 inhibition	+	0.6005	60.05%
CYP2D6 inhibition	-	0.9062	90.62%
CYP1A2 inhibition	+	0.7475	74.75%
CYP2C8 inhibition	+	0.5821	58.21%
CYP inhibitory promiscuity	+	0.6271	62.71%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8320	83.20%
Carcinogenicity (trinary)	Non-required	0.6165	61.65%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8455	84.55%
Skin irritation	-	0.8201	82.01%
Skin corrosion	-	0.9644	96.44%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3760	37.60%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8651	86.51%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9261	92.61%
Acute Oral Toxicity (c)	III	0.6357	63.57%
Estrogen receptor binding	+	0.7321	73.21%
Androgen receptor binding	+	0.7383	73.83%
Thyroid receptor binding	+	0.7723	77.23%
Glucocorticoid receptor binding	+	0.8033	80.33%
Aromatase binding	-	0.5822	58.22%
PPAR gamma	+	0.6144	61.44%
Honey bee toxicity	-	0.8907	89.07%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9623	96.23%

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	99.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.05%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.05%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.38%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.12%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.48%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.93%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.83%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.69%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.06%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	84.47%	88.48%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	84.17%	98.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.62%	99.15%
CHEMBL2581	P07339	Cathepsin D	83.61%	98.95%
CHEMBL4208	P20618	Proteasome component C5	82.66%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.44%	94.45%

Plants that contains it

• Adenopeltis serrata
• Annona squamosa
• Bituminaria bituminosa
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Salacia chinensis
• Salvia coulteri
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Turraeanthus mannii

Cross-Links

• PubChem: 10249800
• NPASS: NPC184613
• LOTUS: LTS0043602
• wikiData: Q105381136