Schisantherin A

Details

• Internal ID: b65321d5-2a90-4d7a-8391-cd7df433b5c5
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(8S,9S,10S)-9-hydroxy-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)-hexaen-8-yl] benzoate
• SMILES (Canonical): CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4C(C1(C)O)OC(=O)C5=CC=CC=C5)OC)OC)OC)OC)OCO3
• SMILES (Isomeric): C[C@H]1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4[C@@H]([C@@]1(C)O)OC(=O)C5=CC=CC=C5)OC)OC)OC)OC)OCO3
• InChI: InChI=1S/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3/t16-,28-,30-/m0/s1
• InChI Key: UFCGDBKFOKKVAC-DSASHONVSA-N
• Popularity: 121 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₂O₉
• Molecular Weight: 536.60 g/mol
• Exact Mass: 536.20463259 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.96
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 58546-56-8
• Gomisin C
• Gomisin
• Gomisin-C
• Schizantherin A
• CHEMBL404875
• UNII-873480KS4A
• 873480KS4A
• CHEBI:9048
• (5S,6S,7S)-6-hydroxy-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]dioxol-5-yl benzoate
• (5S-(5alpha,6beta,7beta))-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
• Benzo(3,4)cycloocta(1,2-f)(1,3)benzodioxole-5,6-diol, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, 5-benzoate, (5S-(5alpha,6beta,7beta))-
• Arisanschinin K
• BENZO(3,4)CYCLOOCTA(1,2-F)(1,3)BENZODIOXOLE-5,6-DIOL, 5,6,7,8-TETRAHYDRO-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYL-, 5-BENZOATE, (5S,6S,7S,13AS)-
• AC1L46IR
• Schizantherin-A
• Wuweizi ester A
• Wuweizi ester-A
• C30H32O9
• Gomisin-C;Schizantherin-A;Wuweizi ester-A
• DTXSID70207261
• MolPort-005-932-873
• BCP15178
• HY-N0694
• BDBM50418091
• MFCD09026937
• AKOS015897145
• C30-H32-O9
• CS-3660
• AC-11195
• AC-34833
• G0538
• Q27108251
• SCHISANTHERIN A (GOMISIN C) (CONSTITUENT OF NORTHERN SCHISANDRA)
• SCHISANTHERIN A (GOMISIN C) (CONSTITUENT OF NORTHERN SCHISANDRA) [DSC]
• [(8S,9S,10S)-9-hydroxy-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)-hexaen-8-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.6045	60.45%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6652	66.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8808	88.08%
OATP1B3 inhibitior	+	0.9272	92.72%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9801	98.01%
P-glycoprotein inhibitior	+	0.9277	92.77%
P-glycoprotein substrate	-	0.6372	63.72%
CYP3A4 substrate	+	0.6743	67.43%
CYP2C9 substrate	-	0.5953	59.53%
CYP2D6 substrate	-	0.8133	81.33%
CYP3A4 inhibition	+	0.8027	80.27%
CYP2C9 inhibition	+	0.5905	59.05%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.7982	79.82%
CYP1A2 inhibition	-	0.7355	73.55%
CYP2C8 inhibition	+	0.7880	78.80%
CYP inhibitory promiscuity	-	0.6340	63.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4536	45.36%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.7717	77.17%
Skin corrosion	-	0.9561	95.61%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6636	66.36%
Micronuclear	+	0.5674	56.74%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.7869	78.69%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.5449	54.49%
Estrogen receptor binding	+	0.8529	85.29%
Androgen receptor binding	+	0.6044	60.44%
Thyroid receptor binding	+	0.6694	66.94%
Glucocorticoid receptor binding	+	0.8756	87.56%
Aromatase binding	+	0.5496	54.96%
PPAR gamma	+	0.7959	79.59%
Honey bee toxicity	-	0.7368	73.68%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5796	57.96%
Fish aquatic toxicity	+	0.9871	98.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	399 nM	Ki	PMID: 16248836

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.00%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.76%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.86%	96.09%
CHEMBL261	P00915	Carbonic anhydrase I	96.26%	96.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.08%	95.56%
CHEMBL2535	P11166	Glucose transporter	92.94%	98.75%
CHEMBL2581	P07339	Cathepsin D	92.23%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.14%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.95%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.13%	99.23%
CHEMBL4208	P20618	Proteasome component C5	85.49%	90.00%
CHEMBL5028	O14672	ADAM10	83.96%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.64%	97.14%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.40%	89.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.02%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.81%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.38%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.04%	96.77%
CHEMBL2056	P21728	Dopamine D1 receptor	80.26%	91.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.25%	94.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.21%	95.50%

Plants that contains it

• Kadsura heteroclita
• Schisandra arisanensis
• Schisandra chinensis
• Schisandra henryi
• Schisandra propinqua
• Schisandra rubriflora
• Schisandra sphenanthera

Cross-Links

• PubChem: 151529
• NPASS: NPC118162
• ChEMBL: CHEMBL404875
• LOTUS: LTS0237905
• wikiData: Q27108251