Schizandrin

Details

• Internal ID: b7a4fd39-d453-4c20-aa83-9c4d0feac05c
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaen-9-ol
• SMILES (Canonical): CC1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3CC1(C)O)OC)OC)OC)OC)OC)OC
• SMILES (Isomeric): CC1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3CC1(C)O)OC)OC)OC)OC)OC)OC
• InChI: InChI=1S/C24H32O7/c1-13-9-14-10-16(26-3)20(28-5)22(30-7)18(14)19-15(12-24(13,2)25)11-17(27-4)21(29-6)23(19)31-8/h10-11,13,25H,9,12H2,1-8H3
• InChI Key: YEFOAORQXAOVJQ-UHFFFAOYSA-N
• Popularity: 189 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₇
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.21480336 g/mol
• Topological Polar Surface Area (TPSA): 75.60 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Schizandrin
• Schizandrol A
• 7432-28-2
• Wuweizichun A
• Wuweizi alcohol A
• Schisandrol A
• Schizandra
• 3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaen-9-ol
• Gomisins
• Wuweizins
• Omija
• Magnolia Vine
• Wu-wei-zi
• Gomisins (Japanese)
• Wuweizins (Chinese)
• Schisandrins (Russian)
• Schisandra chinensis fruit
• UNII-G01BQC0879
• Schisandrin,(S)
• C24H32O7
• SCHEMBL2702845
• CHEBI:80900
• DTXSID20995843
• YEFOAORQXAOVJQ-UHFFFAOYSA-N
• Dibenzo(a,c)cycloocten-6-ol, 5,6,7,8-tetrahydro-1,2,3,10,11,12-hexamethoxy-6,7-dimethyl-, stereoisomer
• Dibenzo(a,c)cycloocten-6-ol, 5,6,7,8-tetrahydro-6,7-dimethyl-1,2 3,10,11,12-hexamethoxy-, stereoisomer
• AKOS015918158
• 1,2,3,10,11,12-hexamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulen-6-ol
• AS-17718
• LS-60873
• FT-0630370
• C17064
• Q-100805
• 1,2,3,10,11,12-Hexamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c]cycloocten-6-ol #
• Dibenzo(a,c)cycloocten-6-ol, 5,6,7,8-tetrahydro-6,7-dimethyl-1,2 3,10,11,12-hexamethoxy-,stereoisomer

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.9292	92.92%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6487	64.87%
OATP2B1 inhibitior	-	0.8661	86.61%
OATP1B1 inhibitior	+	0.9282	92.82%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7481	74.81%
P-glycoprotein inhibitior	-	0.5203	52.03%
P-glycoprotein substrate	-	0.7387	73.87%
CYP3A4 substrate	+	0.5651	56.51%
CYP2C9 substrate	+	0.6456	64.56%
CYP2D6 substrate	+	0.4455	44.55%
CYP3A4 inhibition	-	0.5586	55.86%
CYP2C9 inhibition	-	0.9283	92.83%
CYP2C19 inhibition	-	0.7946	79.46%
CYP2D6 inhibition	-	0.9030	90.30%
CYP1A2 inhibition	+	0.6707	67.07%
CYP2C8 inhibition	-	0.6367	63.67%
CYP inhibitory promiscuity	-	0.9387	93.87%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5559	55.59%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.7410	74.10%
Skin irritation	-	0.7014	70.14%
Skin corrosion	-	0.9494	94.94%
Ames mutagenesis	-	0.7291	72.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.6927	69.27%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8395	83.95%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8308	83.08%
Acute Oral Toxicity (c)	III	0.5908	59.08%
Estrogen receptor binding	+	0.8509	85.09%
Androgen receptor binding	-	0.7803	78.03%
Thyroid receptor binding	+	0.7930	79.30%
Glucocorticoid receptor binding	+	0.7048	70.48%
Aromatase binding	-	0.4868	48.68%
PPAR gamma	+	0.8094	80.94%
Honey bee toxicity	-	0.8903	89.03%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6751	67.51%
Fish aquatic toxicity	+	0.9842	98.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.16%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.30%	86.33%
CHEMBL261	P00915	Carbonic anhydrase I	91.55%	96.76%
CHEMBL217	P14416	Dopamine D2 receptor	91.46%	95.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.18%	92.94%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.23%	85.14%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	86.41%	92.68%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.97%	94.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.92%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.65%	95.89%
CHEMBL2535	P11166	Glucose transporter	83.16%	98.75%
CHEMBL2056	P21728	Dopamine D1 receptor	81.71%	91.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.40%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.28%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.12%	89.50%

Plants that contains it

• Bletilla striata
• Incarvillea mairei
• Kadsura angustifolia
• Schisandra chinensis
• Schisandra henryi
• Schisandra lancifolia
• Schisandra rubriflora
• Schisandra sphenanthera

Cross-Links

• PubChem: 23915
• NPASS: NPC148699
• LOTUS: LTS0077106
• wikiData: Q99542848