2-((2S,3S)-4-((E)-3-((R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy)-3-oxoprop-1-enyl)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrobenzo[b]furan-3-carbonyloxy)-3-(3,4-dihydroxyphenyl)propanoic acid

Details

• Internal ID: 21fc7be3-d745-4be9-a2ad-20166e8aeca1
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R)-2-[(E)-3-[(2S,3S)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=C3C(C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)OC(CC5=CC(=C(C=C5)O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C3[C@@H]([C@H](OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)OC(CC5=CC(=C(C=C5)O)O)C(=O)O)O)O
• InChI: InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28?,31+,32-/m1/s1
• InChI Key: SNKFFCBZYFGCQN-ARBMFGAVSA-N
• Popularity: 631 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₀O₁₆
• Molecular Weight: 718.60 g/mol
• Exact Mass: 718.15338487 g/mol
• Topological Polar Surface Area (TPSA): 278.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

• Salvianolic acid B
• Danfensuan B
• 115939-25-8
• 121521-90-2
• 2-((2S,3S)-4-((E)-3-((R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy)-3-oxoprop-1-enyl)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrobenzo[b]furan-3-carbonyloxy)-3-(3,4-dihydroxyphenyl)propanoic acid
• C36H30O16
• C36-H30-O16
• CHEMBL5190775
• SCHEMBL14916585
• (2R-(2alpha,3beta(R*),4(E(R*))))-3-(1-Carboxy-2-(3,4-dihydroxyphenyl)ethyl) 4-(3-(1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy)-3-oxo-1-propenyl)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylate
• CS-0451942
• Salvianolic acid B; Lithospermic acid B; Danfensuan B
• (2R)-2-[(E)-3-[(2S,3S)-3-[1-Carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
• 2-(((2S,3S)-4-((E)-3-((R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy)-3-oxoprop-1-en-1-yl)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrobenzofuran-3-carbonyl)oxy)-3-(3,4-dihydroxyphenyl)propanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9386	93.86%
Caco-2	-	0.8970	89.70%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7277	72.77%
OATP2B1 inhibitior	-	0.8462	84.62%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6714	67.14%
P-glycoprotein inhibitior	+	0.7351	73.51%
P-glycoprotein substrate	-	0.7177	71.77%
CYP3A4 substrate	+	0.6234	62.34%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.8421	84.21%
CYP3A4 inhibition	-	0.8491	84.91%
CYP2C9 inhibition	+	0.6147	61.47%
CYP2C19 inhibition	-	0.6025	60.25%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	-	0.7427	74.27%
CYP2C8 inhibition	+	0.7176	71.76%
CYP inhibitory promiscuity	-	0.6058	60.58%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.4149	41.49%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8852	88.52%
Skin irritation	-	0.7352	73.52%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7024	70.24%
Micronuclear	+	0.8218	82.18%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8114	81.14%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8718	87.18%
Acute Oral Toxicity (c)	III	0.3187	31.87%
Estrogen receptor binding	+	0.7823	78.23%
Androgen receptor binding	+	0.8153	81.53%
Thyroid receptor binding	-	0.4887	48.87%
Glucocorticoid receptor binding	-	0.4713	47.13%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6760	67.60%
Honey bee toxicity	-	0.6194	61.94%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	99.44%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.23%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.99%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.86%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL3194	P02766	Transthyretin	90.83%	90.71%
CHEMBL233	P35372	Mu opioid receptor	90.47%	97.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.70%	96.00%
CHEMBL4040	P28482	MAP kinase ERK2	89.22%	83.82%
CHEMBL2581	P07339	Cathepsin D	88.79%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.54%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.16%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.87%	99.15%
CHEMBL236	P41143	Delta opioid receptor	85.15%	99.35%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.05%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.76%	91.19%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.62%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	82.26%	94.73%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.26%	94.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.04%	91.71%

Plants that contains it

• Arnebia euchroma
• Arnebia guttata
• Euphorbia pekinensis
• Lithospermum erythrorhizon
• Mentha arvensis
• Mentha canadensis
• Salvia miltiorrhiza

Cross-Links

• PubChem: 6449855
• NPASS: NPC189197