Mulberroside A

Details

• Internal ID: e72a6374-0b75-47a6-b39a-582e406f4b3e
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-hydroxy-4-[(E)-2-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)O)C=CC3=CC(=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)/C=C/C3=CC(=CC(=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H32O14/c27-9-17-19(31)21(33)23(35)25(39-17)37-14-4-3-12(16(30)8-14)2-1-11-5-13(29)7-15(6-11)38-26-24(36)22(34)20(32)18(10-28)40-26/h1-8,17-36H,9-10H2/b2-1+/t17-,18-,19-,20-,21+,22+,23-,24-,25-,26-/m1/s1
• InChI Key: HPSWAEGGWLOOKT-VUNDNAJOSA-N
• Popularity: 31 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₄
• Molecular Weight: 568.50 g/mol
• Exact Mass: 568.17920569 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• 102841-42-9
• cis-Mulberroside A
• OJU5SVA08B
• (2S,3R,4S,5S,6R)-2-[3-hydroxy-4-[(E)-2-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• N1520
• MulberrosideA
• Mulberroside-A
• UNII-OJU5SVA08B
• CHEMBL455619
• SCHEMBL22498775
• CHEBI:177974
• DTXSID901030445
• HY-N0619
• BDBM50529592
• MFCD16294844
• s9075
• AKOS030526209
• CCG-270083
• CS-4679
• AC-34709
• AS-56590
• A904166
• Q-100952
• Q6933784
• [2,5'-dihydroxy-4,3'-bis(beta-d-glucopyranosyloxy)-trans-stilbene]
• .BETA.-D-GLUCOPYRANOSIDE, 3-((1E)-2-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2-HYDROXYPHENYL)ETHENYL)-5-HYDROXYPHENYL
• 2-[2-[3-Hydroxy-5-(beta-D-glucopyranosyloxy)phenyl]ethenyl]-5-(beta-D-glucopyranosyloxy)phenol
• 3-((1E)-2-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2-HYDROXYPHENYL)ETHENYL)-5-HYDROXYPHENYL .BETA.-D-GLUCOPYRANOSIDE
• 3-{(E)-2-[4-(beta-D-glucopyranosyloxy)-2-hydroxyphenyl]ethenyl}-5-hydroxyphenyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8398	83.98%
Caco-2	-	0.9050	90.50%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5500	55.00%
OATP2B1 inhibitior	+	0.5730	57.30%
OATP1B1 inhibitior	+	0.9337	93.37%
OATP1B3 inhibitior	+	0.9663	96.63%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6086	60.86%
P-glycoprotein inhibitior	-	0.5469	54.69%
P-glycoprotein substrate	-	0.9425	94.25%
CYP3A4 substrate	+	0.5240	52.40%
CYP2C9 substrate	+	0.5811	58.11%
CYP2D6 substrate	-	0.8191	81.91%
CYP3A4 inhibition	-	0.9180	91.80%
CYP2C9 inhibition	-	0.8946	89.46%
CYP2C19 inhibition	-	0.8435	84.35%
CYP2D6 inhibition	-	0.8871	88.71%
CYP1A2 inhibition	-	0.9318	93.18%
CYP2C8 inhibition	+	0.5608	56.08%
CYP inhibitory promiscuity	-	0.6530	65.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6312	63.12%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8889	88.89%
Skin irritation	-	0.8468	84.68%
Skin corrosion	-	0.9637	96.37%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7805	78.05%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.8644	86.44%
skin sensitisation	-	0.8030	80.30%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.6393	63.93%
Acute Oral Toxicity (c)	III	0.5907	59.07%
Estrogen receptor binding	+	0.6901	69.01%
Androgen receptor binding	-	0.5671	56.71%
Thyroid receptor binding	+	0.5443	54.43%
Glucocorticoid receptor binding	-	0.6482	64.82%
Aromatase binding	+	0.6177	61.77%
PPAR gamma	+	0.8020	80.20%
Honey bee toxicity	-	0.7306	73.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8165	81.65%

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	99.66%	91.11%
CHEMBL3194	P02766	Transthyretin	94.28%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.91%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.89%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.30%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.70%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.18%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.92%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.36%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.72%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	88.38%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	87.98%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.74%	99.17%
CHEMBL2581	P07339	Cathepsin D	87.23%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.51%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.86%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.29%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.08%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.44%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.02%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.95%	95.83%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.88%	88.00%

Plants that contains it

• Morus alba
• Morus nigra
• Schoenocaulon officinale
• Veratrum dahuricum

Cross-Links

• PubChem: 6443484
• NPASS: NPC8497
• LOTUS: LTS0039129
• wikiData: Q6933784