Symplocosin

Details

• Internal ID: 6d704663-f417-45b8-bac9-137add51635d
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 2-[4-[3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)O
• InChI: InChI=1S/C26H32O11/c1-32-18-7-12(3-5-16(18)28)24-14-10-35-25(15(14)11-34-24)13-4-6-17(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20-31H,9-11H2,1-2H3
• InChI Key: QLJNETOQFQXTLI-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₁
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.19446183 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• 11042-30-1
• 24404-49-7
• epipinoresinol-4'-O-glucopyranoside
• 2-[4-[3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• EPIPINORESINOL-4-O-GLUCOPYRANOSIDE
• (+)-Piresil-4-O-beta-D-glucopyraside
• 69251-96-3
• (+)-pinoresinol 4-O-beta-D-glucopyranoside
• 74983-66-7
• NSC35608
• Compound NP-000892
• MLS000876969
• MEGxp0_000349
• CHEMBL1302893
• ACon1_001148
• DTXSID90417709
• CHEBI:139469
• HMS2269N21
• BCP10898
• Epipinoresinol-4'-O-beta-D-glucoside
• AKOS040740113
• NCGC00169630-01
• NCGC00169630-02
• SMR000440667
• (+)-Piresil-4-O-(c)micro-D-glucopyraside
• FT-0775801
• BRD-A30201120-001-01-8
• (+)-Piresil-4-O-beta-D-glucopyraside; Pinoresinol 4-O-beta-D-glucopyranoside; Pinoresinol 4-O-glucoside; (+)-pinoresinol-(c)micro-D-glucoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5501	55.01%
Caco-2	-	0.8307	83.07%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7266	72.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8901	89.01%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6373	63.73%
P-glycoprotein inhibitior	-	0.4567	45.67%
P-glycoprotein substrate	-	0.8245	82.45%
CYP3A4 substrate	+	0.5675	56.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7876	78.76%
CYP3A4 inhibition	-	0.8406	84.06%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.7124	71.24%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.8560	85.60%
CYP2C8 inhibition	+	0.5818	58.18%
CYP inhibitory promiscuity	-	0.5107	51.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9299	92.99%
Skin irritation	-	0.8431	84.31%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8069	80.69%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8863	88.63%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9156	91.56%
Acute Oral Toxicity (c)	III	0.6689	66.89%
Estrogen receptor binding	+	0.7114	71.14%
Androgen receptor binding	+	0.6271	62.71%
Thyroid receptor binding	+	0.6191	61.91%
Glucocorticoid receptor binding	+	0.6088	60.88%
Aromatase binding	-	0.5565	55.65%
PPAR gamma	+	0.6097	60.97%
Honey bee toxicity	-	0.8482	84.82%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9086	90.86%

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	98.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.56%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.18%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.30%	92.94%
CHEMBL2581	P07339	Cathepsin D	89.66%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.32%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.62%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.45%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.28%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.09%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.56%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.73%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.51%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.30%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.02%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.70%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.40%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.65%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.32%	97.14%

Plants that contains it

• Abies nephrolepis
• Acer truncatum
• Arnica mollis
• Arum italicum
• Baccharis dracunculifolia
• Balanophora abbreviata
• Balanophora japonica
• Balanophora laxiflora
• Berberis koreana
• Brucea javanica
• Carex distachya
• Clematis hexapetala
• Daphne acutiloba
• Daphne feddei
• Daphne giraldii
• Daphne oleoides
• Epimedium sagittatum
• Forsythia japonica
• Forsythia koreana
• Ipomoea nil
• Macaranga tanarius
• Narthecium asiaticum
• Pedicularis densispica
• Pinus massoniana
• Prunus domestica
• Rubus amabilis
• Saussurea medusa
• Sesamum indicum
• Strychnos axillaris
• Symplocos glomerata
• Syringa reticulata
• Tinospora sinensis
• Vitex glabrata

Cross-Links

• PubChem: 5351523
• LOTUS: LTS0002400
• wikiData: Q82227825