Yatein

Details

• Internal ID: e8575c09-3e4d-484b-a395-36077c408280
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: (3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)CC2C(COC2=O)CC3=CC4=C(C=C3)OCO4
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C[C@@H]2[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4
• InChI: InChI=1S/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1
• InChI Key: GMLDZDDTZKXJLU-JKSUJKDBSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₇
• Molecular Weight: 400.40 g/mol
• Exact Mass: 400.15220310 g/mol
• Topological Polar Surface Area (TPSA): 72.40 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 40456-50-6
• (-)-yatein
• Dihydroanhydropodorhizol
• (-)-deoxypodorhizone
• Deoxypodorhizone
• CHEBI:4553
• CHEMBL471067
• 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-((3,4,5-trimethoxyphenyl)methyl)-, trans-(-)-
• (3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• (3~{R},4~{R})-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• (3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]tetrahydrofuran-2-one
• 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-[(3,4,5-trimethoxyphenyl)methyl]-, (3R,4R)-
• AC1L9DHE
• Deoxypodorhizon
• YTN
• D01FBL
• SCHEMBL1037807
• DTXSID50193471
• GMLDZDDTZKXJLU-JKSUJKDBSA-N
• HY-N1060
• BDBM50241524
• AKOS032948829
• MS-26796
• RD4-6277
• CS-0016340
• Q27106408
• (-)-trans-3-(3,4-Methylenedioxybenzyl)-2-(3,4,5-trimethoxybenzyl)butyrolactone
• (3R,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one
• (3r,4r)-4-(1,3-benzodioxol-5-ylmethyl) dihydro-3-[(3,4,5-trimethoxyphenyl)methyl]-2(3h)-furanone
• (3R,4R)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• (3R,4R)-4-(Benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one
• (3R,4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-[(3,4,5-trimethoxyphenyl)methyl]-, (3R-trans)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	+	0.7276	72.76%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7652	76.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9345	93.45%
OATP1B3 inhibitior	+	0.9640	96.40%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9379	93.79%
P-glycoprotein inhibitior	+	0.8022	80.22%
P-glycoprotein substrate	-	0.8381	83.81%
CYP3A4 substrate	+	0.5569	55.69%
CYP2C9 substrate	+	0.5905	59.05%
CYP2D6 substrate	-	0.7552	75.52%
CYP3A4 inhibition	+	0.9242	92.42%
CYP2C9 inhibition	+	0.8450	84.50%
CYP2C19 inhibition	+	0.9606	96.06%
CYP2D6 inhibition	-	0.5450	54.50%
CYP1A2 inhibition	+	0.5438	54.38%
CYP2C8 inhibition	-	0.6329	63.29%
CYP inhibitory promiscuity	+	0.9161	91.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4853	48.53%
Eye corrosion	-	0.9816	98.16%
Eye irritation	-	0.8558	85.58%
Skin irritation	-	0.8509	85.09%
Skin corrosion	-	0.9751	97.51%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8023	80.23%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.5856	58.56%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4762	47.62%
Acute Oral Toxicity (c)	III	0.5818	58.18%
Estrogen receptor binding	+	0.9003	90.03%
Androgen receptor binding	+	0.6610	66.10%
Thyroid receptor binding	+	0.6214	62.14%
Glucocorticoid receptor binding	+	0.7267	72.67%
Aromatase binding	-	0.6540	65.40%
PPAR gamma	+	0.6951	69.51%
Honey bee toxicity	-	0.7164	71.64%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9899	98.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	1000 nM	IC50	PMID: 15679319

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.20%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.34%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.98%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.94%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.73%	92.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.63%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.53%	94.80%
CHEMBL2581	P07339	Cathepsin D	95.47%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.65%	85.14%
CHEMBL261	P00915	Carbonic anhydrase I	90.39%	96.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.63%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.39%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.71%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.65%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.01%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.04%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.88%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.05%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.08%	97.25%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.26%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.85%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.24%	94.73%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Anthriscus sylvestris
• Aquilaria malaccensis
• Arcangelisia gusanlung
• Arctium lappa
• Artemisia schmidtiana
• Austrocedrus chilensis
• Avena fatua
• Brickellia pendula
• Bupleurum scorzonerifolium
• Bursera simaruba
• Calocedrus formosana
• Chaerophyllum aureum
• Chamaecyparis obtusa
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Condea verticillata
• Copaifera paupera
• Crotalaria spectabilis
• Endosamara racemosa
• Entandrophragma cylindricum
• Eriope blanchetii
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Helichrysum fulvum
• Hernandia cordigera
• Hernandia nymphaeifolia
• Hernandia sonora
• Hesperocyparis nevadensis
• Illigera luzonensis
• Jacobaea erratica
• Juniperus brevifolia
• Juniperus communis
• Juniperus sabina
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Lychnophora ericoides
• Macrococculus pomiferus
• Magnolia acuminata
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Piper cubeba
• Piper guineense
• Piper sylvaticum
• Plectranthus amboinicus
• Plumbago europaea
• Podolepis rugata
• Reissantia indica
• Rhodanthe stricta
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Thuja occidentalis
• Thuja plicata
• Timonius kaniensis

Cross-Links

• PubChem: 442835
• NPASS: NPC210354
• ChEMBL: CHEMBL471067
• LOTUS: LTS0144117
• wikiData: Q27106408