3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxyoxan-2-yl]methoxy]propanoic acid

Details

• Internal ID: 86f4d73f-309a-4471-ae71-572bbed10bd4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxyoxan-2-yl]methoxy]propanoic acid
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)OC4C(C(C(C(O4)COC(=O)CC(=O)O)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]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC(=O)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C30H32O18/c31-9-18-22(37)24(39)26(41)30(47-18)46-17-7-14-15(44-28(17)11-1-3-12(32)4-2-11)5-13(33)6-16(14)45-29-27(42)25(40)23(38)19(48-29)10-43-21(36)8-20(34)35/h1-7,18-19,22-27,29-31,37-42H,8-10H2,(H2-,32,33,34,35)/p+1/t18-,19-,22-,23-,24+,25+,26-,27-,29-,30-/m1/s1
• InChI Key: XAUWJGQEHRUDEM-IEKHAQANSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₃O₁₈+
• Molecular Weight: 681.60 g/mol
• Exact Mass: 681.16668920 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.82
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7926	79.26%
Caco-2	-	0.9095	90.95%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.5257	52.57%
OATP2B1 inhibitior	-	0.8415	84.15%
OATP1B1 inhibitior	+	0.8841	88.41%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7893	78.93%
P-glycoprotein inhibitior	+	0.6018	60.18%
P-glycoprotein substrate	-	0.7518	75.18%
CYP3A4 substrate	+	0.6223	62.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8548	85.48%
CYP3A4 inhibition	-	0.9204	92.04%
CYP2C9 inhibition	-	0.9430	94.30%
CYP2C19 inhibition	-	0.8961	89.61%
CYP2D6 inhibition	-	0.9294	92.94%
CYP1A2 inhibition	-	0.8936	89.36%
CYP2C8 inhibition	+	0.8429	84.29%
CYP inhibitory promiscuity	-	0.9440	94.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6698	66.98%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9039	90.39%
Skin irritation	-	0.8329	83.29%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7680	76.80%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9073	90.73%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7993	79.93%
Acute Oral Toxicity (c)	III	0.4367	43.67%
Estrogen receptor binding	+	0.7791	77.91%
Androgen receptor binding	+	0.6180	61.80%
Thyroid receptor binding	-	0.5123	51.23%
Glucocorticoid receptor binding	-	0.5182	51.82%
Aromatase binding	+	0.5622	56.22%
PPAR gamma	+	0.6532	65.32%
Honey bee toxicity	-	0.8004	80.04%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.8964	89.64%

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	98.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.41%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.01%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.85%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.72%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.59%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.17%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.32%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.17%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.11%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	84.85%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.22%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	82.07%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.57%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.97%	95.56%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.89%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	80.84%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.26%	95.83%

Plants that contains it

• Aconitum fischeri
• Apocynum androsaemifolium
• Espeletia grandiflora
• Huperzia yunnanensis
• Hyacinthus orientalis
• Lagascea mollis
• Pulmonaria mollis
• Rosa rugosa
• Tetracera alnifolia

Cross-Links

• PubChem: 101930173
• NPASS: NPC126106