Silyamandin

Details

• Internal ID: 3d7c814c-2d54-454c-903e-3c7d255647bd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: (3aR,4R,5R,7aR)-4-(4-hydroxy-3-methoxyphenyl)-1-oxo-7-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-3a,4,5,7a-tetrahydro-3H-2-benzofuran-5-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC(=O)C3C(=CC2C(=O)O)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@@H]2[C@H]3COC(=O)[C@H]3C(=C[C@H]2C(=O)O)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)O
• InChI: InChI=1S/C25H22O11/c1-34-16-4-9(2-3-14(16)27)18-12(24(31)32)7-11(19-13(18)8-35-25(19)33)23-22(30)21(29)20-15(28)5-10(26)6-17(20)36-23/h2-7,12-13,18-19,22-23,26-28,30H,8H2,1H3,(H,31,32)/t12-,13-,18+,19+,22+,23-/m1/s1
• InChI Key: BVNNAIYNHUXFCR-QRVGLHCZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂O₁₁
• Molecular Weight: 498.40 g/mol
• Exact Mass: 498.11621151 g/mol
• Topological Polar Surface Area (TPSA): 180.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 1009565-36-9
• (3aR,4R,5R,7aR)-4-(4-hydroxy-3-methoxyphenyl)-1-oxo-7-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-3a,4,5,7a-tetrahydro-3H-2-benzofuran-5-carboxylic acid
• DTXSID50858699
• EX-A3714
• HY-N8180
• AKOS040762349
• CS-0140265
• E88952

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9660	96.60%
Caco-2	-	0.8745	87.45%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7513	75.13%
OATP2B1 inhibitior	-	0.5664	56.64%
OATP1B1 inhibitior	+	0.8925	89.25%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8910	89.10%
P-glycoprotein inhibitior	+	0.6325	63.25%
P-glycoprotein substrate	-	0.6177	61.77%
CYP3A4 substrate	+	0.6583	65.83%
CYP2C9 substrate	-	0.5913	59.13%
CYP2D6 substrate	-	0.8574	85.74%
CYP3A4 inhibition	+	0.5552	55.52%
CYP2C9 inhibition	+	0.8964	89.64%
CYP2C19 inhibition	+	0.8011	80.11%
CYP2D6 inhibition	-	0.8335	83.35%
CYP1A2 inhibition	-	0.5449	54.49%
CYP2C8 inhibition	+	0.6799	67.99%
CYP inhibitory promiscuity	+	0.8803	88.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4486	44.86%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.8332	83.32%
Skin irritation	-	0.7574	75.74%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6785	67.85%
Micronuclear	+	0.8474	84.74%
Hepatotoxicity	+	0.7045	70.45%
skin sensitisation	-	0.7862	78.62%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6864	68.64%
Acute Oral Toxicity (c)	III	0.4874	48.74%
Estrogen receptor binding	+	0.8224	82.24%
Androgen receptor binding	+	0.7535	75.35%
Thyroid receptor binding	-	0.5719	57.19%
Glucocorticoid receptor binding	+	0.7118	71.18%
Aromatase binding	-	0.7027	70.27%
PPAR gamma	-	0.4843	48.43%
Honey bee toxicity	-	0.7445	74.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9797	97.97%

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	98.76%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.57%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.84%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.70%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.88%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.26%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.20%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.11%	85.14%
CHEMBL2535	P11166	Glucose transporter	89.54%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.59%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.48%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.78%	99.17%
CHEMBL2581	P07339	Cathepsin D	86.77%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.38%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	84.39%	91.19%
CHEMBL4208	P20618	Proteasome component C5	83.83%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.18%	94.00%
CHEMBL3194	P02766	Transthyretin	81.71%	90.71%

Plants that contains it

• Silybum marianum

Cross-Links

• PubChem: 23634490
• NPASS: NPC95463