(6aR,11aR)-8-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol

Details

• Internal ID: cfab59fe-b60e-4187-8488-8e38bb60f6ea
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (6aR,11aR)-8-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
• SMILES (Canonical): COC1=C(C=C2C(=C1)C3COC4=C(C3O2)C=CC(=C4)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)[C@@H]3COC4=C([C@@H]3O2)C=CC(=C4)O)O
• InChI: InChI=1S/C16H14O5/c1-19-15-5-10-11-7-20-13-4-8(17)2-3-9(13)16(11)21-14(10)6-12(15)18/h2-6,11,16-18H,7H2,1H3/t11-,16-/m0/s1
• InChI Key: NYGZYUAVZPIKBZ-ZBEGNZNMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.72
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• lespedezol D1
• CHEBI:132852

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9700	97.00%
Caco-2	+	0.6070	60.70%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7867	78.67%
OATP2B1 inhibitior	-	0.8612	86.12%
OATP1B1 inhibitior	+	0.9125	91.25%
OATP1B3 inhibitior	+	0.9782	97.82%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6832	68.32%
P-glycoprotein inhibitior	-	0.8393	83.93%
P-glycoprotein substrate	-	0.7040	70.40%
CYP3A4 substrate	+	0.5506	55.06%
CYP2C9 substrate	-	0.7778	77.78%
CYP2D6 substrate	+	0.4927	49.27%
CYP3A4 inhibition	-	0.5996	59.96%
CYP2C9 inhibition	+	0.7556	75.56%
CYP2C19 inhibition	+	0.8833	88.33%
CYP2D6 inhibition	+	0.6318	63.18%
CYP1A2 inhibition	+	0.9016	90.16%
CYP2C8 inhibition	+	0.7290	72.90%
CYP inhibitory promiscuity	+	0.8529	85.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4232	42.32%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.5105	51.05%
Skin irritation	-	0.7187	71.87%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5810	58.10%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.7904	79.04%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7111	71.11%
Acute Oral Toxicity (c)	III	0.7722	77.22%
Estrogen receptor binding	+	0.5957	59.57%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.7741	77.41%
Glucocorticoid receptor binding	+	0.7096	70.96%
Aromatase binding	-	0.5987	59.87%
PPAR gamma	+	0.7324	73.24%
Honey bee toxicity	-	0.8485	84.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5951	59.51%
Fish aquatic toxicity	+	0.7595	75.95%

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	97.37%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.62%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.41%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.74%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.42%	95.56%
CHEMBL2535	P11166	Glucose transporter	88.87%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.88%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.86%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.86%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.76%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.71%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.08%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.82%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.54%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	82.32%	83.82%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	82.30%	95.55%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.01%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.89%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.10%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.73%	95.89%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.52%	100.00%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Lespedeza homoloba
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 21676223
• NPASS: NPC265496
• LOTUS: LTS0256240
• wikiData: Q105187504