Anhydrosecoisolariciresinol

Details

• Internal ID: b149160a-d3c7-452c-a5d1-18eba1380569
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans
• IUPAC Name: 4-[[(3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COCC2CC3=CC(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@H]2COC[C@@H]2CC3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
• InChI Key: ROGUIJKVZZROIQ-HOTGVXAUSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.16
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 29388-33-8
• CHEMBL367448
• 4-[[(3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol
• 4,4'-[(3R,4R)-oxolane-3,4-diylbis(methylene)]bis(2-methoxyphenol)
• 4,4'-(((3R,4R)-Tetrahydrofuran-3,4-diyl)bis(methylene))bis(2-methoxyphenol)
• (?)-3,4-Divanilyltetrahydrofuran
• (-)-3,4-divanillyltetrahydrofuran
• HY-N6990
• BDBM50240916
• AKOS040760271
• MS-25285
• CS-0101437
• (3R,4R)-3,4-Bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran
• 4-[4-(4-hydroxy-3-methoxybenzyl)-(3R,4R)-tetrahydro-3-furanylmethyl]-2-methoxyphenol
• 4-[[(3R,4R)-4-[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-3-yl]methyl]-2-methoxy-phenol
• P5G

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9635	96.35%
Caco-2	+	0.7304	73.04%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8905	89.05%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6744	67.44%
P-glycoprotein inhibitior	+	0.6968	69.68%
P-glycoprotein substrate	-	0.8666	86.66%
CYP3A4 substrate	-	0.5722	57.22%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	+	0.4702	47.02%
CYP3A4 inhibition	+	0.6534	65.34%
CYP2C9 inhibition	+	0.6786	67.86%
CYP2C19 inhibition	+	0.8403	84.03%
CYP2D6 inhibition	-	0.7807	78.07%
CYP1A2 inhibition	+	0.6637	66.37%
CYP2C8 inhibition	+	0.5953	59.53%
CYP inhibitory promiscuity	+	0.8913	89.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8325	83.25%
Carcinogenicity (trinary)	Non-required	0.5362	53.62%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.6487	64.87%
Skin irritation	-	0.8547	85.47%
Skin corrosion	-	0.9672	96.72%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8410	84.10%
Micronuclear	-	0.5226	52.26%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.7248	72.48%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8190	81.90%
Acute Oral Toxicity (c)	III	0.6295	62.95%
Estrogen receptor binding	+	0.8770	87.70%
Androgen receptor binding	+	0.7104	71.04%
Thyroid receptor binding	+	0.7236	72.36%
Glucocorticoid receptor binding	+	0.6639	66.39%
Aromatase binding	+	0.6376	63.76%
PPAR gamma	+	0.5510	55.10%
Honey bee toxicity	-	0.9048	90.48%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5851	58.51%
Fish aquatic toxicity	+	0.9598	95.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3305	P04278	Testis-specific androgen-binding protein	2600 nM; 309.03 nM	IC50; Kd	PMID: 9461660; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3305	P04278	Testis-specific androgen-binding protein	100.00%	0.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.92%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.31%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.35%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.93%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.50%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.75%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.83%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.19%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.89%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.32%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	80.36%	83.82%

Plants that contains it

• Achillea micrantha
• Bidens cernua
• Calocedrus formosana
• Crucianella maritima
• Dracaena draco
• Euphorbia cheiradenia
• Iris pallida
• Kadsura heteroclita
• Maytenus apurimacensis
• Pentzia calva
• Plazia daphnoides
• Sphagneticola calendulacea
• Symphonia globulifera
• Tetracera sarmentosa
• Urtica dioica

Cross-Links

• PubChem: 9974771
• NPASS: NPC31344
• ChEMBL: CHEMBL367448
• LOTUS: LTS0014635
• wikiData: Q105242207