(3S,4S,6S)-2-(hydroxymethyl)-6-[7-hydroxy-3-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxyoxane-3,4,5-triol

Details

• Internal ID: 6288fa26-19cd-4e09-922d-da68b0ec9ef2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: (3S,4S,6S)-2-(hydroxymethyl)-6-[7-hydroxy-3-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C2=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
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C2=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
• InChI: InChI=1S/C27H30O17/c28-6-16-19(34)21(36)23(38)26(43-16)41-14-4-9(30)3-13-10(14)5-15(25(40-13)8-1-11(31)18(33)12(32)2-8)42-27-24(39)22(37)20(35)17(7-29)44-27/h1-5,16-17,19-24,26-29,34-39H,6-7H2,(H3-,30,31,32,33)/p+1/t16?,17?,19-,20-,21+,22?,23?,24?,26-,27-/m1/s1
• InChI Key: XCTGXGVGJYACEI-XDBCTHHXSA-O
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₁O₁₇+
• Molecular Weight: 627.50 g/mol
• Exact Mass: 627.15612452 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -2.44
• H-Bond Acceptor: 16
• H-Bond Donor: 12
• Rotatable Bonds: 7

Synonyms

• LMPK12010283

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8494	84.94%
Caco-2	-	0.9145	91.45%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Nucleus	0.4431	44.31%
OATP2B1 inhibitior	-	0.5551	55.51%
OATP1B1 inhibitior	+	0.8903	89.03%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5222	52.22%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8342	83.42%
CYP3A4 substrate	+	0.5583	55.83%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8268	82.68%
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	+	0.7682	76.82%
CYP inhibitory promiscuity	-	0.7658	76.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6229	62.29%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8768	87.68%
Skin irritation	-	0.8185	81.85%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.6691	66.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7978	79.78%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.7750	77.50%
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	-	0.8237	82.37%
Acute Oral Toxicity (c)	IV	0.4162	41.62%
Estrogen receptor binding	+	0.7033	70.33%
Androgen receptor binding	+	0.6012	60.12%
Thyroid receptor binding	+	0.5474	54.74%
Glucocorticoid receptor binding	-	0.5078	50.78%
Aromatase binding	+	0.6438	64.38%
PPAR gamma	+	0.6653	66.53%
Honey bee toxicity	-	0.7905	79.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5949	59.49%
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	99.52%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.60%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.66%	83.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.55%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.00%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.68%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	90.19%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.07%	92.94%
CHEMBL3194	P02766	Transthyretin	88.85%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.68%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.39%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	85.16%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.16%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.76%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.40%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.75%	92.62%
CHEMBL1937	Q92769	Histone deacetylase 2	81.14%	94.75%
CHEMBL2424	Q04760	Glyoxalase I	80.97%	91.67%
CHEMBL2581	P07339	Cathepsin D	80.33%	98.95%

Plants that contains it

• Aconitum carmichaelii
• Clitoria ternatea
• Commelina communis
• Crocus antalyensis
• Crocus sieberi
• Delphinium ajacis
• Delphinium flexuosum
• Hydrophyllum virginianum
• Medicago sativa
• Penstemon centranthifolius
• Phaseolus vulgaris
• Punica granatum
• Puya chilensis
• Rhododendron simsii
• Vitis vinifera

Cross-Links

• PubChem: 44256888
• NPASS: NPC181574
• LOTUS: LTS0256765
• wikiData: Q104387627