Schisandrin B

Details

• Internal ID: e3653db3-358a-466d-8ba2-369471ab8243
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaene
• SMILES (Canonical): CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4CC1C)OC)OC)OC)OC)OCO3
• SMILES (Isomeric): CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4CC1C)OC)OC)OC)OC)OCO3
• InChI: InChI=1S/C23H28O6/c1-12-7-14-9-16(24-3)20(25-4)22(26-5)18(14)19-15(8-13(12)2)10-17-21(23(19)27-6)29-11-28-17/h9-10,12-13H,7-8,11H2,1-6H3
• InChI Key: RTZKSTLPRTWFEV-UHFFFAOYSA-N
• Popularity: 347 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.18858861 g/mol
• Topological Polar Surface Area (TPSA): 55.40 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.49
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 61281-37-6
• Schizandrin B
• gamma-Schisandrin
• Gamma-schizandrin
• CHEMBL479488
• Schizandrin-B;Wuweizisu-B;gamma-Schisandrin
• 3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaene
• UNII-02XA4X3KZW
• S(-) Schisandrin B
• Schizandrin-B
• 1,2,3,13-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxole
• |A-Schisandrin
• S(-) Wuweizisu B
• Gamma-Schisandrin ,(S)
• SCHEMBL3380716
• DTXSID60976772
• GLXC-19128
• HMS3652I13
• BCP30085
• Benzo(3,4)cycloocta(1,2-f)(1,3)benzodioxole, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, stereoisomer
• HY-N0089
• BDBM50341711
• AKOS015897166
• CCG-208607
• CS-3659
• NCGC00163663-01
• LS-33970
• FT-0775855
• Schisandrin B; Wuweizisu-B; gamma-Schisandrin
• SR-05000002175
• Q-100707
• SR-05000002175-2
• (5S,6S,7S,13aS)-5,6,7,8-Tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethylbenzo[3,4]cycloocta[1,2-f][1,3] benzodioxole-5,6-diol 5-Benzoate
• 1,2,3,13-Tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydro-11H-benzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxole
• Benzo[3,4]cycloocta[1,2-f][1,3]benzodioxole,5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, stereoisomer

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.9407	94.07%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5357	53.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9315	93.15%
OATP1B3 inhibitior	+	0.9570	95.70%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9296	92.96%
P-glycoprotein inhibitior	+	0.6640	66.40%
P-glycoprotein substrate	-	0.8579	85.79%
CYP3A4 substrate	+	0.5330	53.30%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	+	0.4065	40.65%
CYP3A4 inhibition	+	0.8480	84.80%
CYP2C9 inhibition	+	0.7007	70.07%
CYP2C19 inhibition	+	0.7741	77.41%
CYP2D6 inhibition	+	0.6565	65.65%
CYP1A2 inhibition	+	0.6737	67.37%
CYP2C8 inhibition	-	0.6257	62.57%
CYP inhibitory promiscuity	+	0.8039	80.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9408	94.08%
Carcinogenicity (trinary)	Non-required	0.4246	42.46%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.7929	79.29%
Skin irritation	-	0.7890	78.90%
Skin corrosion	-	0.9693	96.93%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8349	83.49%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.7021	70.21%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7821	78.21%
Acute Oral Toxicity (c)	III	0.6141	61.41%
Estrogen receptor binding	+	0.7969	79.69%
Androgen receptor binding	-	0.7286	72.86%
Thyroid receptor binding	+	0.7302	73.02%
Glucocorticoid receptor binding	+	0.7928	79.28%
Aromatase binding	-	0.5250	52.50%
PPAR gamma	+	0.7085	70.85%
Honey bee toxicity	-	0.7801	78.01%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5024	Q13535	Serine-protein kinase ATR	7200 nM; 7300 nM	IC50; IC50	PMID: 21413798; PMID: 22835870

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL261	P00915	Carbonic anhydrase I	96.25%	96.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.32%	96.77%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	91.19%	96.86%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.97%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.39%	82.67%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.68%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.36%	92.62%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	88.18%	94.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.36%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.57%	89.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.23%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.11%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.74%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.67%	100.00%
CHEMBL2535	P11166	Glucose transporter	82.08%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.00%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.28%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	80.92%	95.12%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.58%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.36%	97.14%

Plants that contains it

• Panax ginseng
• Schisandra chinensis
• Schisandra lancifolia
• Schisandra rubriflora
• Schisandra sphenanthera
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 108130
• NPASS: NPC185680
• ChEMBL: CHEMBL479488
• LOTUS: LTS0171074
• wikiData: Q72507130