(+)-(8S,8'R)-4-hydroxy-3,3',4',5'-tetramethoxylignan

Details

• Internal ID: 4e5725e9-d461-4dd3-b93f-6d87581b1358
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[(2S,3R)-2,3-dimethyl-4-(3,4,5-trimethoxyphenyl)butyl]-2-methoxyphenol
• InChI: InChI=1S/C22H30O5/c1-14(9-16-7-8-18(23)19(11-16)24-3)15(2)10-17-12-20(25-4)22(27-6)21(13-17)26-5/h7-8,11-15,23H,9-10H2,1-6H3/t14-,15+/m0/s1
• InChI Key: HDQFIVFINXJTNV-LSDHHAIUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.50 g/mol
• Exact Mass: 374.20932405 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• (+)-(8S,8'R)-4-hydroxy-3,3',4',5'-tetramethoxylignan
• 4-[(2S,3R)-2,3-Dimethyl-4-(3,4,5-trimethoxyphenyl)butyl]-2-methoxyphenol
• 4-((2S,3R)-2,3-dimethyl-4-(3,4,5-trimethoxyphenyl)butyl)-2-methoxyphenol
• RefChem:67181
• CHEMBL1812789
• Q27136653

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.8834	88.34%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8177	81.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9278	92.78%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5927	59.27%
P-glycoprotein inhibitior	+	0.7812	78.12%
P-glycoprotein substrate	-	0.8890	88.90%
CYP3A4 substrate	-	0.6180	61.80%
CYP2C9 substrate	+	0.5965	59.65%
CYP2D6 substrate	+	0.4548	45.48%
CYP3A4 inhibition	-	0.6760	67.60%
CYP2C9 inhibition	-	0.8808	88.08%
CYP2C19 inhibition	+	0.5613	56.13%
CYP2D6 inhibition	-	0.6339	63.39%
CYP1A2 inhibition	+	0.6563	65.63%
CYP2C8 inhibition	+	0.7028	70.28%
CYP inhibitory promiscuity	-	0.5560	55.60%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7550	75.50%
Carcinogenicity (trinary)	Non-required	0.6439	64.39%
Eye corrosion	-	0.9740	97.40%
Eye irritation	-	0.7843	78.43%
Skin irritation	-	0.8155	81.55%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8880	88.80%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7948	79.48%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	-	0.8395	83.95%
Acute Oral Toxicity (c)	III	0.7151	71.51%
Estrogen receptor binding	+	0.7838	78.38%
Androgen receptor binding	-	0.5087	50.87%
Thyroid receptor binding	+	0.6637	66.37%
Glucocorticoid receptor binding	+	0.6811	68.11%
Aromatase binding	+	0.6476	64.76%
PPAR gamma	+	0.7134	71.34%
Honey bee toxicity	-	0.9126	91.26%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.9942	99.42%

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	97.08%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.39%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.06%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.84%	99.15%
CHEMBL2581	P07339	Cathepsin D	91.71%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	91.28%	90.20%
CHEMBL2535	P11166	Glucose transporter	90.46%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.42%	94.45%
CHEMBL3492	P49721	Proteasome Macropain subunit	89.97%	90.24%
CHEMBL4208	P20618	Proteasome component C5	87.20%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.93%	89.62%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	83.89%	92.68%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.87%	92.62%

Plants that contains it

• Machilus robusta

Cross-Links

• PubChem: 53359577
• NPASS: NPC137440