Wedelolactone

Details

• Internal ID: 698ee248-57de-4633-80e8-95ef8b99cbcb
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Coumestans
• IUPAC Name: 1,8,9-trihydroxy-3-methoxy-[1]benzofuro[3,2-c]chromen-6-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=O)C3=C2OC4=CC(=C(C=C43)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=O)C3=C2OC4=CC(=C(C=C43)O)O)O
• InChI: InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3
• InChI Key: XQDCKJKKMFWXGB-UHFFFAOYSA-N
• Popularity: 359 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₀O₇
• Molecular Weight: 314.25 g/mol
• Exact Mass: 314.04265265 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 524-12-9
• 7-Methoxy-5,11,12-trihydroxycoumestan
• 7-Methoxy-5,11,12-trihydroxy-coumestan
• IKK Inhibitor II
• 1,8,9-Trihydroxy-3-methoxycoumestan
• UNII-0K6L725GNS
• CHEMBL97453
• 0K6L725GNS
• CHEBI:10037
• 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one
• 5,11,12-Trihydroxy-7-methoxycoumestan
• 1,8,9-trihydroxy-3-methoxy-[1]benzofuro[3,2-c]chromen-6-one
• 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy-
• 1,8,9-Trihydroxy-3-methoxy-6H-[1]benzofuro[3,2-c]chromen-6-one
• 1,8,9-TRIHYDROXY-3-METHOXY-6H-(1)BENZOFURO(3,2-C)CHROMEN-6-ONE
• MFCD07778564
• 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one
• D0F8QJ
• SCHEMBL601220
• GTPL5551
• DTXSID60200408
• Wedelolactone, analytical standard
• 1,8,9-trihydroxy-3-methoxy-benzofuro[3,2-c]chromen-6-one
• HMS2043P19
• BCP19859
• C16H10O7
• HY-N0551
• BDBM50096619
• HB4124
• LMPK12090046
• s9042
• AKOS015897173
• CCG-208289
• SMP2_000112
• NCGC00163667-01
• NCGC00163667-02
• NCGC00163667-03
• Wedelolactone, >=98% (HPLC), powder
• AC-34562
• CS-0009079
• FT-0698529
• W0015
• A14804
• K00058
• A936784
• SR-05000002318
• Q6586709
• SR-05000002318-2
• BRD-K53635676-001-01-5
• BRD-K53635676-001-02-3
• Wedelolactone; 7-Methoxy-5,11,12-trihydroxy-coumestan
• B0005-464576
• 1,8,9-trihydroxy-3-methoxy-[1]benzoxolo[3,2-c]chromen-6-one
• Wedelolactone, European Pharmacopoeia (EP) Reference Standard
• 1,8,9-Trihydroxy-3-methoxy-benzo[4,5]furo[3,2-c]chromen-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9352	93.52%
Caco-2	-	0.6864	68.64%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7687	76.87%
OATP2B1 inhibitior	-	0.5656	56.56%
OATP1B1 inhibitior	+	0.9373	93.73%
OATP1B3 inhibitior	+	0.9763	97.63%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9131	91.31%
P-glycoprotein inhibitior	-	0.7135	71.35%
P-glycoprotein substrate	-	0.9007	90.07%
CYP3A4 substrate	-	0.5118	51.18%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.6101	61.01%
CYP2C9 inhibition	-	0.7604	76.04%
CYP2C19 inhibition	+	0.7410	74.10%
CYP2D6 inhibition	-	0.6626	66.26%
CYP1A2 inhibition	+	0.8474	84.74%
CYP2C8 inhibition	-	0.7351	73.51%
CYP inhibitory promiscuity	-	0.5328	53.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.3606	36.06%
Eye corrosion	-	0.9779	97.79%
Eye irritation	+	0.7632	76.32%
Skin irritation	-	0.6400	64.00%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8974	89.74%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8470	84.70%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7121	71.21%
Acute Oral Toxicity (c)	III	0.5546	55.46%
Estrogen receptor binding	+	0.8617	86.17%
Androgen receptor binding	+	0.8658	86.58%
Thyroid receptor binding	+	0.6274	62.74%
Glucocorticoid receptor binding	+	0.9105	91.05%
Aromatase binding	+	0.7246	72.46%
PPAR gamma	+	0.8491	84.91%
Honey bee toxicity	-	0.8308	83.08%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9211	92.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	2500 nM	IC50	PMID: 11212092
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	2511.9 nM; 11220.2 nM; 14125.4 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	12589.3 nM; 17782.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5586	P16152	Carbonyl reductase [NADPH] 1	3780 nM; 600 nM	IC50; Ki	PMID: 19097799; via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	4466.8 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	50118.7 nM; 35481.3 nM; 39810.7 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	1000 nM; 707.9 nM; 707.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.82%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.67%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.90%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.39%	99.15%
CHEMBL2581	P07339	Cathepsin D	89.19%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.16%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.87%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.57%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.35%	99.17%
CHEMBL3194	P02766	Transthyretin	84.20%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.36%	86.33%
CHEMBL2535	P11166	Glucose transporter	82.97%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	82.17%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	82.06%	91.49%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.42%	94.42%

Plants that contains it

• Aconitum kongboense
• Eclipta prostrata
• Eclipta prostrata
• Ephedra intermedia
• Garcinia lucida
• Hypericum erectum
• Platycladus orientalis
• Sphagneticola calendulacea

Cross-Links

• PubChem: 5281813
• NPASS: NPC86477
• ChEMBL: CHEMBL97453
• LOTUS: LTS0216902
• wikiData: Q6586709