Sibiricose A5

Details

• Internal ID: 2c9a0e9d-c47b-4b05-8fd4-19579abf829c
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(OC2(CO)OC3C(C(C(C(O3)CO)O)O)O)CO)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O)O
• InChI: InChI=1S/C22H30O14/c1-32-12-6-10(2-4-11(12)26)3-5-15(27)34-20-17(29)14(8-24)35-22(20,9-25)36-21-19(31)18(30)16(28)13(7-23)33-21/h2-6,13-14,16-21,23-26,28-31H,7-9H2,1H3/b5-3+/t13-,14-,16-,17-,18+,19-,20+,21-,22+/m1/s1
• InChI Key: ZPEADZHVGOCGKH-YQTDNFGYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₁₄
• Molecular Weight: 518.50 g/mol
• Exact Mass: 518.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -3.42
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• 107912-97-0
• [(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 3-O-Feruloylsucrose
• SibiricoseA5
• CHEBI:189459
• DTXSID301347739
• HY-N2167
• NCGC00384564-01
• MS-29614
• CS-0019467
• 3-O-(3-Methoxy-4-hydroxycinnamoyl)-beta-D-fructofuranosyl alpha-D-glucopyranoside
• (2S,3S,4R,5R)-4-Hydroxy-2,5-bis(hydroxymethyl)-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuran-3-yl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate
• (2S,3S,4R,5R)-4-HYDROXY-2,5-BIS(HYDROXYMETHYL)-2-{[(2R,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}OXOLAN-3-YL (2E)-3-(4-HYDROXY-3-METHOXYPHENYL)PROP-2-ENOATE
• NCGC00384564-01_C22H30O14_3-O-[(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoyl]-beta-D-fructofuranosyl alpha-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7383	73.83%
Caco-2	-	0.9089	90.89%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7601	76.01%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.8850	88.50%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7548	75.48%
P-glycoprotein inhibitior	-	0.7195	71.95%
P-glycoprotein substrate	-	0.7440	74.40%
CYP3A4 substrate	+	0.6204	62.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.8192	81.92%
CYP2C9 inhibition	-	0.8331	83.31%
CYP2C19 inhibition	-	0.7423	74.23%
CYP2D6 inhibition	-	0.8953	89.53%
CYP1A2 inhibition	-	0.8898	88.98%
CYP2C8 inhibition	+	0.7181	71.81%
CYP inhibitory promiscuity	-	0.5905	59.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6227	62.27%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9410	94.10%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6655	66.55%
Micronuclear	-	0.6226	62.26%
Hepatotoxicity	-	0.8824	88.24%
skin sensitisation	-	0.8039	80.39%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8938	89.38%
Acute Oral Toxicity (c)	III	0.7020	70.20%
Estrogen receptor binding	+	0.8321	83.21%
Androgen receptor binding	+	0.5547	55.47%
Thyroid receptor binding	+	0.5215	52.15%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6458	64.58%
PPAR gamma	+	0.6891	68.91%
Honey bee toxicity	-	0.7557	75.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7963	79.63%

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	99.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.42%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.38%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.34%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.90%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.04%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.12%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.69%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.55%	94.73%
CHEMBL3194	P02766	Transthyretin	89.32%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.73%	94.45%
CHEMBL4208	P20618	Proteasome component C5	84.18%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.05%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.61%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.42%	89.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.64%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.57%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.53%	92.62%

Plants that contains it

• Arnebia guttata
• Cryptocarya liebertiana
• Cryptocarya moschata
• Cryptocarya myrtifolia
• Cyclamen purpurascens
• Glaucium flavum
• Lilium speciosum
• Polygala arillata
• Polygala sibirica
• Sesbania bispinosa

Cross-Links

• PubChem: 6326020
• NPASS: NPC21836
• LOTUS: LTS0122373
• wikiData: Q105134416