Petunidin 3-O-[6-O-(4-O-(E)-p-coumaroyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside

Details

• Internal ID: 52fe1f48-6437-4b06-a105-30b64a46f867
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: [(3R,4R,6R)-6-[[(3S,6S)-6-[2-(3,4-dihydroxy-5-methoxyphenyl)-7-hydroxy-5-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C([O+]=C4C=C(C=C(C4=C3)OC5C(C(C(C(O5)CO)O)O)O)O)C6=CC(=C(C(=C6)OC)O)O)O)O)O)O)O)OC(=O)C=CC7=CC=C(C=C7)O
• SMILES (Isomeric): CC1[C@@H]([C@@H](C([C@@H](O1)OCC2[C@H](C(C([C@@H](O2)OC3=C([O+]=C4C=C(C=C(C4=C3)O[C@H]5C([C@H]([C@@H](C(O5)CO)O)O)O)O)C6=CC(=C(C(=C6)OC)O)O)O)O)O)O)O)OC(=O)/C=C/C7=CC=C(C=C7)O
• InChI: InChI=1S/C43H48O23/c1-16-39(66-29(48)8-5-17-3-6-19(45)7-4-17)35(54)38(57)41(60-16)59-15-28-32(51)34(53)37(56)43(65-28)63-26-13-21-23(61-40(26)18-9-22(47)30(49)25(10-18)58-2)11-20(46)12-24(21)62-42-36(55)33(52)31(50)27(14-44)64-42/h3-13,16,27-28,31-39,41-44,50-57H,14-15H2,1-2H3,(H3-,45,46,47,48,49)/p+1/t16?,27?,28?,31-,32-,33+,34?,35-,36?,37?,38?,39+,41-,42-,43-/m1/s1
• InChI Key: BXEZTCOKOLHMKY-ABWSONMJSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₉O₂₃+
• Molecular Weight: 933.80 g/mol
• Exact Mass: 933.26646281 g/mol
• Topological Polar Surface Area (TPSA): 355.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.31
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 13

Synonyms

• Petunidin 3-O-[6-O-(4-O-(E)-p-coumaroyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside
• LMPK12010362

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7097	70.97%
Caco-2	-	0.8750	87.50%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.4435	44.35%
OATP2B1 inhibitior	-	0.7183	71.83%
OATP1B1 inhibitior	+	0.8292	82.92%
OATP1B3 inhibitior	+	0.9733	97.33%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7362	73.62%
P-glycoprotein inhibitior	+	0.7142	71.42%
P-glycoprotein substrate	+	0.6638	66.38%
CYP3A4 substrate	+	0.6948	69.48%
CYP2C9 substrate	-	0.8071	80.71%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9351	93.51%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.8674	86.74%
CYP2D6 inhibition	-	0.9170	91.70%
CYP1A2 inhibition	-	0.9085	90.85%
CYP2C8 inhibition	+	0.8759	87.59%
CYP inhibitory promiscuity	-	0.6676	66.76%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6697	66.97%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.8261	82.61%
Skin corrosion	-	0.9516	95.16%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8145	81.45%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8966	89.66%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9390	93.90%
Acute Oral Toxicity (c)	III	0.6468	64.68%
Estrogen receptor binding	+	0.8026	80.26%
Androgen receptor binding	+	0.5702	57.02%
Thyroid receptor binding	+	0.5616	56.16%
Glucocorticoid receptor binding	+	0.7049	70.49%
Aromatase binding	+	0.6173	61.73%
PPAR gamma	+	0.7628	76.28%
Honey bee toxicity	-	0.7003	70.03%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8607	86.07%

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	99.70%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.01%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.62%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.49%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.33%	96.00%
CHEMBL3194	P02766	Transthyretin	95.21%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.57%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.51%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.44%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.15%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.92%	89.62%
CHEMBL2581	P07339	Cathepsin D	89.21%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.00%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	87.75%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.39%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.72%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.29%	94.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	85.74%	97.31%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.38%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.47%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.68%	92.62%
CHEMBL4208	P20618	Proteasome component C5	82.94%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.66%	86.92%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.10%	91.71%

Plants that contains it

• Solanum tuberosum

Cross-Links

• PubChem: 44256967
• LOTUS: LTS0179906
• wikiData: Q104947899