(3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(R)-hydroxy-(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one

Details

• Internal ID: 8b9014d7-6b66-48f1-8c52-d4c3e8215027
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: (3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(R)-hydroxy-(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C(C2C(COC2=O)CC3=CC4=C(C=C3)OCO4)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@@H]([C@@H]2[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4)O
• InChI: InChI=1S/C22H24O8/c1-25-17-8-13(9-18(26-2)21(17)27-3)20(23)19-14(10-28-22(19)24)6-12-4-5-15-16(7-12)30-11-29-15/h4-5,7-9,14,19-20,23H,6,10-11H2,1-3H3/t14-,19-,20-/m0/s1
• InChI Key: UNWCWBJEKCTIML-GKCIPKSASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₈
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.14711772 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• (3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(R)-hydroxy-(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• (3alpha(R*),4beta)-(+-)-4-(1,3-Benzodioxol-5-ylmethyl)-dihydro-3-(hydroxy(3,4,5-trimethoxyphenyl)methyl)-2(3H)-furanone
• Epipodorhizol
• 17187-82-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9476	94.76%
Caco-2	+	0.5876	58.76%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7339	73.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.5600	56.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9418	94.18%
P-glycoprotein inhibitior	+	0.7489	74.89%
P-glycoprotein substrate	-	0.7435	74.35%
CYP3A4 substrate	+	0.5547	55.47%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	-	0.7519	75.19%
CYP3A4 inhibition	+	0.7423	74.23%
CYP2C9 inhibition	+	0.9065	90.65%
CYP2C19 inhibition	+	0.9068	90.68%
CYP2D6 inhibition	-	0.6347	63.47%
CYP1A2 inhibition	-	0.7702	77.02%
CYP2C8 inhibition	-	0.6973	69.73%
CYP inhibitory promiscuity	+	0.8714	87.14%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4129	41.29%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8894	88.94%
Skin irritation	-	0.8056	80.56%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6480	64.80%
Micronuclear	+	0.7174	71.74%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7326	73.26%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8472	84.72%
Acute Oral Toxicity (c)	III	0.4478	44.78%
Estrogen receptor binding	+	0.8950	89.50%
Androgen receptor binding	+	0.6729	67.29%
Thyroid receptor binding	+	0.6063	60.63%
Glucocorticoid receptor binding	+	0.7593	75.93%
Aromatase binding	-	0.6790	67.90%
PPAR gamma	+	0.7416	74.16%
Honey bee toxicity	-	0.7629	76.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9435	94.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.49%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.49%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.35%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL261	P00915	Carbonic anhydrase I	97.42%	96.76%
CHEMBL2581	P07339	Cathepsin D	96.81%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.67%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.13%	92.62%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	92.35%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.13%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.94%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.52%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.68%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.13%	96.00%
CHEMBL4208	P20618	Proteasome component C5	86.22%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.93%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.69%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.25%	95.50%
CHEMBL2535	P11166	Glucose transporter	85.01%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	84.81%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.05%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.00%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.14%	89.50%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Condea verticillata
• Copaifera paupera
• Crotalaria spectabilis
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hernandia sonora
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus sabina
• 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

Cross-Links

• PubChem: 173676
• NPASS: NPC310512
• LOTUS: LTS0124816
• wikiData: Q104402838