[(2R,3S,4S)-2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)oxolan-3-yl]methanol

Details

• Internal ID: f79548f6-6124-4a58-be70-2b496173ccbc
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 7,9-epoxylignans
• IUPAC Name: [(2R,3S,4S)-2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)oxolan-3-yl]methanol
• SMILES (Canonical): C1C(C(C(O1)C2=CC3=C(C=C2)OCO3)CO)CC4=CC5=C(C=C4)OCO5
• SMILES (Isomeric): C1[C@H]([C@H]([C@@H](O1)C2=CC3=C(C=C2)OCO3)CO)CC4=CC5=C(C=C4)OCO5
• InChI: InChI=1S/C20H20O6/c21-8-15-14(5-12-1-3-16-18(6-12)25-10-23-16)9-22-20(15)13-2-4-17-19(7-13)26-11-24-17/h1-4,6-7,14-15,20-21H,5,8-11H2/t14-,15-,20+/m1/s1
• InChI Key: JOCPSXXUQJXDBI-SXGZJXTBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.12598835 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 83708-70-7
• (?)-Dihydrosesamin
• AKOS040761628

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9490	94.90%
Caco-2	+	0.5784	57.84%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7361	73.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9106	91.06%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9326	93.26%
P-glycoprotein inhibitior	+	0.6281	62.81%
P-glycoprotein substrate	-	0.9212	92.12%
CYP3A4 substrate	-	0.5426	54.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6570	65.70%
CYP3A4 inhibition	+	0.6053	60.53%
CYP2C9 inhibition	+	0.6677	66.77%
CYP2C19 inhibition	+	0.6609	66.09%
CYP2D6 inhibition	+	0.5125	51.25%
CYP1A2 inhibition	+	0.6750	67.50%
CYP2C8 inhibition	-	0.7749	77.49%
CYP inhibitory promiscuity	+	0.8163	81.63%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4639	46.39%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7684	76.84%
Skin irritation	-	0.6858	68.58%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	+	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8027	80.27%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.5675	56.75%
skin sensitisation	-	0.8198	81.98%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7660	76.60%
Acute Oral Toxicity (c)	III	0.5291	52.91%
Estrogen receptor binding	+	0.8416	84.16%
Androgen receptor binding	+	0.7649	76.49%
Thyroid receptor binding	+	0.5606	56.06%
Glucocorticoid receptor binding	-	0.5719	57.19%
Aromatase binding	+	0.5323	53.23%
PPAR gamma	+	0.7606	76.06%
Honey bee toxicity	-	0.8598	85.98%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9818	98.18%

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	98.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.21%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.91%	97.09%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	90.31%	85.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.92%	92.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.46%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.77%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.34%	94.80%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.80%	96.77%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.58%	89.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.13%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.79%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.61%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.23%	99.17%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Daphne tangutica
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Plectranthus amboinicus
• Plumbago europaea
• Reissantia indica
• Rhodanthe stricta
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis
• Wikstroemia canescens

Cross-Links

• PubChem: 11653313
• NPASS: NPC255961
• LOTUS: LTS0184484
• wikiData: Q105132261