Scirpusin A

Details

• Internal ID: fc4eb151-9494-4342-800b-07c1e8ffd862
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC(=C(C=C4)O)O)C5=CC(=CC(=C5)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=C3C(C(OC3=CC(=C2)O)C4=CC(=C(C=C4)O)O)C5=CC(=CC(=C5)O)O)O
• InChI: InChI=1S/C28H22O7/c29-19-6-2-15(3-7-19)1-4-16-9-22(32)14-25-26(16)27(18-10-20(30)13-21(31)11-18)28(35-25)17-5-8-23(33)24(34)12-17/h1-14,27-34H/b4-1+
• InChI Key: VJVQHVVOEFJLIO-DAFODLJHSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₂O₇
• Molecular Weight: 470.50 g/mol
• Exact Mass: 470.13655304 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 5.36
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 69297-51-4
• NSC374718
• (E)-4-(3-(3,5-dihydroxyphenyl)-6-hydroxy-4-(4-hydroxystyryl)-2,3-dihydrobenzofuran-2-yl)benzene-1,2-diol
• 1,2-Benzenediol, 4-(3-(3,5-dihydroxyphenyl)-2,3-dihydro-6-hydroxy-4-(2-(4-hydroxyphenyl)ethenyl)-2-benzofuranyl)-
• C28H22O7
• C28-H22-O7
• CHEMBL478595
• SCHEMBL15440886
• NSC-374718
• 4-[3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol
• SCIRPUSIN A (12442:66-4B)
• 2-(3,4-Dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-6-hydroxy-4-(4-hydroxystyryl)-2,3-dihydrobenzofuran

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9727	97.27%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4187	41.87%
OATP2B1 inhibitior	+	0.5668	56.68%
OATP1B1 inhibitior	+	0.8869	88.69%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7615	76.15%
P-glycoprotein inhibitior	+	0.5730	57.30%
P-glycoprotein substrate	-	0.9037	90.37%
CYP3A4 substrate	+	0.5209	52.09%
CYP2C9 substrate	+	0.6176	61.76%
CYP2D6 substrate	-	0.6658	66.58%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.6675	66.75%
CYP2C19 inhibition	-	0.6853	68.53%
CYP2D6 inhibition	-	0.8758	87.58%
CYP1A2 inhibition	+	0.8769	87.69%
CYP2C8 inhibition	+	0.7700	77.00%
CYP inhibitory promiscuity	+	0.9240	92.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.3733	37.33%
Eye corrosion	-	0.9879	98.79%
Eye irritation	+	0.6201	62.01%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8336	83.36%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6869	68.69%
skin sensitisation	-	0.6015	60.15%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.4662	46.62%
Acute Oral Toxicity (c)	II	0.3678	36.78%
Estrogen receptor binding	+	0.6218	62.18%
Androgen receptor binding	+	0.8404	84.04%
Thyroid receptor binding	+	0.7258	72.58%
Glucocorticoid receptor binding	+	0.7315	73.15%
Aromatase binding	+	0.5852	58.52%
PPAR gamma	+	0.8207	82.07%
Honey bee toxicity	-	0.8033	80.33%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9823	98.23%

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	99.31%	91.11%
CHEMBL3194	P02766	Transthyretin	97.13%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	96.63%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.17%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.14%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.12%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.23%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	85.84%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.98%	89.67%
CHEMBL242	Q92731	Estrogen receptor beta	84.40%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.38%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.63%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.20%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.07%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.27%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.85%	94.45%

Plants that contains it

• Bolboschoenus fluviatilis
• Bolboschoenus maritimus subsp. maritimus
• Caragana tibetica
• Cyperus rotundus
• Maackia amurensis
• Picea jezoensis subsp. jezoensis
• Schoenoplectus californicus
• Smilax china
• Smilax glabra

Cross-Links

• PubChem: 5458896
• NPASS: NPC173203
• LOTUS: LTS0244024
• wikiData: Q104402529