(2S,4S,5S)-2-[7-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 9cb1b643-7964-4861-a22a-754e6d722ef1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: (2S,4S,5S)-2-[7-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O[C@H]4C([C@H]([C@@H](C(O4)CO)O)O)O)O[C@H]5C(C([C@@H](C(O5)CO)O)O)O)O
• InChI: InChI=1S/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1/t17?,18?,19-,20-,21+,22?,23?,24?,26-,27-/m1/s1
• InChI Key: SLCKJKWFULXZBD-DHXMCCLBSA-O
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₁O₁₅+
• Molecular Weight: 595.50 g/mol
• Exact Mass: 595.16629528 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.85
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

• LMPK12010015

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8494	84.94%
Caco-2	-	0.9181	91.81%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Nucleus	0.4431	44.31%
OATP2B1 inhibitior	-	0.5563	55.63%
OATP1B1 inhibitior	+	0.9041	90.41%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6105	61.05%
P-glycoprotein inhibitior	-	0.5452	54.52%
P-glycoprotein substrate	-	0.8734	87.34%
CYP3A4 substrate	+	0.5597	55.97%
CYP2C9 substrate	-	0.8053	80.53%
CYP2D6 substrate	-	0.8220	82.20%
CYP3A4 inhibition	-	0.9662	96.62%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.8149	81.49%
CYP2D6 inhibition	-	0.9110	91.10%
CYP1A2 inhibition	-	0.8934	89.34%
CYP2C8 inhibition	+	0.8480	84.80%
CYP inhibitory promiscuity	-	0.7658	76.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6229	62.29%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8858	88.58%
Skin irritation	-	0.8185	81.85%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6984	69.84%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.8071	80.71%
skin sensitisation	-	0.9093	90.93%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7493	74.93%
Acute Oral Toxicity (c)	IV	0.4162	41.62%
Estrogen receptor binding	+	0.7398	73.98%
Androgen receptor binding	+	0.6513	65.13%
Thyroid receptor binding	+	0.5646	56.46%
Glucocorticoid receptor binding	-	0.4798	47.98%
Aromatase binding	+	0.6765	67.65%
PPAR gamma	+	0.6704	67.04%
Honey bee toxicity	-	0.7765	77.65%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.7348	73.48%

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	98.47%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	92.11%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.44%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	91.23%	95.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.74%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.59%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.75%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.57%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.09%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	86.80%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.39%	92.94%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.77%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.28%	99.15%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	82.68%	96.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.37%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.29%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.23%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.79%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.75%	86.92%

Plants that contains it

• Alcea rosea
• Amelanchier spicata
• Berberis vulgaris
• Fragaria × ananassa
• Fragaria vesca
• Hibiscus syriacus
• Paeonia suffruticosa
• Penstemon centranthifolius
• Vaccinium uliginosum

Cross-Links

• PubChem: 44256620
• LOTUS: LTS0129471
• wikiData: Q104387043