meso-Secoisolariciresinol

Details

• Internal ID: e4869a95-17dc-42af-9fc3-0ad507a1425a
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans > Dibenzylbutanediol lignans
• IUPAC Name: (2S,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC(CO)C(CC2=CC(=C(C=C2)O)OC)CO)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@H](CO)[C@@H](CC2=CC(=C(C=C2)O)OC)CO)O
• InChI: InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16+
• InChI Key: PUETUDUXMCLALY-IYBDPMFKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9378	93.78%
Caco-2	+	0.5058	50.58%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8966	89.66%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9157	91.57%
OATP1B3 inhibitior	+	0.9348	93.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4568	45.68%
P-glycoprotein inhibitior	-	0.4395	43.95%
P-glycoprotein substrate	-	0.8682	86.82%
CYP3A4 substrate	-	0.6289	62.89%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.4255	42.55%
CYP3A4 inhibition	-	0.5137	51.37%
CYP2C9 inhibition	-	0.5549	55.49%
CYP2C19 inhibition	+	0.6283	62.83%
CYP2D6 inhibition	-	0.8490	84.90%
CYP1A2 inhibition	+	0.6381	63.81%
CYP2C8 inhibition	+	0.5859	58.59%
CYP inhibitory promiscuity	+	0.6134	61.34%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7460	74.60%
Carcinogenicity (trinary)	Non-required	0.6732	67.32%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.7695	76.95%
Skin irritation	-	0.8239	82.39%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	-	0.7644	76.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.8163	81.63%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.6922	69.22%
skin sensitisation	-	0.7735	77.35%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8240	82.40%
Acute Oral Toxicity (c)	III	0.7568	75.68%
Estrogen receptor binding	+	0.8019	80.19%
Androgen receptor binding	+	0.7500	75.00%
Thyroid receptor binding	+	0.6727	67.27%
Glucocorticoid receptor binding	+	0.6204	62.04%
Aromatase binding	+	0.5691	56.91%
PPAR gamma	+	0.5331	53.31%
Honey bee toxicity	-	0.9095	90.95%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.9503	95.03%

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	96.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.16%	91.11%
CHEMBL1255126	O15151	Protein Mdm4	93.22%	90.20%
CHEMBL2581	P07339	Cathepsin D	93.12%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.12%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.47%	94.45%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.93%	90.24%
CHEMBL2535	P11166	Glucose transporter	87.62%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.57%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.04%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.32%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.89%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.69%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.40%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.97%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.28%	89.62%

Plants that contains it

• Achlys triphylla
• Albizia procera
• Artemisia giraldii
• Bulbophyllum protractum
• Calystegia pubescens
• Cedrus deodara
• Cypripedium calceolus
• Diospyros japonica
• Hortonia floribunda
• Hymenocallis littoralis
• Juniperus chinensis
• Lactuca sativa
• Lampranthus sociorum
• Larix sibirica
• Perymenium mendezii
• Picea glauca
• Pongamia pinnata
• Protium tonkinense
• Rubia yunnanensis
• Seriphidium porrectum
• Tarchonanthus camphoratus
• Uncaria rhynchophylla

Cross-Links

• PubChem: 11552274
• NPASS: NPC272537
• LOTUS: LTS0201516
• wikiData: Q105215043