(6aS,12aS)-6abeta,12abeta-Dihydro-3-methoxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran

Details

• Internal ID: 930c59ca-be3f-451f-949a-1624b825839c
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (1S,12S)-16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaene
• SMILES (Canonical): COC1=CC2=C(C=C1)C3C(CO2)C4=CC5=C(C=C4O3)OCO5
• SMILES (Isomeric): COC1=CC2=C(C=C1)[C@@H]3[C@H](CO2)C4=CC5=C(C=C4O3)OCO5
• InChI: InChI=1S/C17H14O5/c1-18-9-2-3-10-13(4-9)19-7-12-11-5-15-16(21-8-20-15)6-14(11)22-17(10)12/h2-6,12,17H,7-8H2,1H3/t12-,17-/m1/s1
• InChI Key: YLZYAUCOYZKLMA-SJKOYZFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29 g/mol
• Exact Mass: 298.08412354 g/mol
• Topological Polar Surface Area (TPSA): 46.20 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.03
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• CHEMBL1983713
• NSC-649972
• NCI60_017420
• (6aS,12aS)-6abeta,12abeta-Dihydro-3-methoxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	+	0.7578	75.78%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6093	60.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9311	93.11%
OATP1B3 inhibitior	+	0.9838	98.38%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7534	75.34%
P-glycoprotein inhibitior	-	0.4935	49.35%
P-glycoprotein substrate	-	0.8505	85.05%
CYP3A4 substrate	+	0.5151	51.51%
CYP2C9 substrate	-	0.8202	82.02%
CYP2D6 substrate	+	0.3802	38.02%
CYP3A4 inhibition	+	0.8103	81.03%
CYP2C9 inhibition	+	0.8053	80.53%
CYP2C19 inhibition	+	0.9555	95.55%
CYP2D6 inhibition	+	0.9395	93.95%
CYP1A2 inhibition	+	0.8851	88.51%
CYP2C8 inhibition	-	0.6275	62.75%
CYP inhibitory promiscuity	+	0.9298	92.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Warning	0.4712	47.12%
Eye corrosion	-	0.9637	96.37%
Eye irritation	-	0.6220	62.20%
Skin irritation	-	0.7183	71.83%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4425	44.25%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.6319	63.19%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6226	62.26%
Acute Oral Toxicity (c)	III	0.8047	80.47%
Estrogen receptor binding	+	0.7708	77.08%
Androgen receptor binding	+	0.5804	58.04%
Thyroid receptor binding	+	0.7701	77.01%
Glucocorticoid receptor binding	+	0.6564	65.64%
Aromatase binding	-	0.6562	65.62%
PPAR gamma	+	0.7045	70.45%
Honey bee toxicity	-	0.8639	86.39%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.7842	78.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2039	P27338	Monoamine oxidase B	98.60%	92.51%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.80%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.34%	94.80%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.57%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.87%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.90%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.40%	92.62%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	90.99%	95.55%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.89%	95.56%
CHEMBL240	Q12809	HERG	90.35%	89.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.20%	86.33%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.06%	80.96%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.60%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.22%	94.45%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	85.11%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.97%	97.14%
CHEMBL2581	P07339	Cathepsin D	83.42%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	83.31%	93.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.23%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	82.49%	95.93%
CHEMBL4208	P20618	Proteasome component C5	80.63%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.31%	94.00%

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
• Lathyrus odoratus
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Ononis viscosa subsp. breviflora
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Pterocarpus macrocarpus
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 373519
• NPASS: NPC58137
• LOTUS: LTS0239693
• wikiData: Q105350421