[(3S,4S,6S)-6-[5-[5-[(2S,4S,5S)-6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-3-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-2-yl]-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 075f9889-8f5b-4c62-9c3d-7fae10260ad2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanidin 5-O-p-coumaroyl glycosides > Anthocyanidin 5-O-6-p-coumaroyl glycosides
• IUPAC Name: [(3S,4S,6S)-6-[5-[5-[(2S,4S,5S)-6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-3-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-2-yl]-2,3-dihydroxyphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=CC(=CC(=C3O)O)C4=C(C=C5C(=CC(=CC5=[O+]4)O)OC6C(C(C(C(O6)COC(=O)C=CC7=CC(=C(C=C7)O)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C=CC(=O)OCC2[C@H]([C@@H](C([C@@H](O2)OC3=CC(=CC(=C3O)O)C4=C(C=C5C(=CC(=CC5=[O+]4)O)O[C@H]6C([C@H]([C@@H](C(O6)COC(=O)C=CC7=CC(=C(C=C7)O)O)O)O)O)O[C@H]8C(C([C@@H](C(O8)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C51H52O28/c52-16-33-39(62)42(65)45(68)51(77-33)76-32-15-23-29(13-22(53)14-30(23)74-49-46(69)43(66)40(63)34(78-49)17-71-36(59)7-3-19-1-5-24(54)26(56)9-19)73-48(32)21-11-28(58)38(61)31(12-21)75-50-47(70)44(67)41(64)35(79-50)18-72-37(60)8-4-20-2-6-25(55)27(57)10-20/h1-15,33-35,39-47,49-52,62-70H,16-18H2,(H6-,53,54,55,56,57,58,59,60,61)/p+1/t33?,34?,35?,39-,40-,41-,42?,43+,44+,45?,46?,47?,49-,50-,51-/m1/s1
• InChI Key: CMHKKALEZOJWDP-SYEACPEDSA-O
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₅₃O₂₈+
• Molecular Weight: 1113.90 g/mol
• Exact Mass: 1113.27233603 g/mol
• Topological Polar Surface Area (TPSA): 453.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.62
• H-Bond Acceptor: 27
• H-Bond Donor: 17
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7695	76.95%
Caco-2	-	0.8626	86.26%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Nucleus	0.4984	49.84%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8672	86.72%
OATP1B3 inhibitior	+	0.9736	97.36%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8613	86.13%
P-glycoprotein inhibitior	+	0.7398	73.98%
P-glycoprotein substrate	-	0.6467	64.67%
CYP3A4 substrate	+	0.6568	65.68%
CYP2C9 substrate	-	0.8045	80.45%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	-	0.9408	94.08%
CYP2C9 inhibition	-	0.8977	89.77%
CYP2C19 inhibition	-	0.8553	85.53%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	-	0.9141	91.41%
CYP2C8 inhibition	+	0.8673	86.73%
CYP inhibitory promiscuity	-	0.8246	82.46%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6709	67.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8977	89.77%
Skin irritation	-	0.8257	82.57%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.5437	54.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8132	81.32%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8765	87.65%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8751	87.51%
Acute Oral Toxicity (c)	IV	0.3956	39.56%
Estrogen receptor binding	+	0.6944	69.44%
Androgen receptor binding	+	0.7068	70.68%
Thyroid receptor binding	+	0.6008	60.08%
Glucocorticoid receptor binding	+	0.6165	61.65%
Aromatase binding	+	0.5566	55.66%
PPAR gamma	+	0.7409	74.09%
Honey bee toxicity	-	0.7222	72.22%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9324	93.24%

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	99.74%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.31%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.26%	89.00%
CHEMBL3194	P02766	Transthyretin	96.45%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.27%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.71%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.47%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.57%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.67%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.77%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.11%	94.73%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.88%	83.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.51%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.31%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.11%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.57%	86.92%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.89%	80.78%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 57126444
• NPASS: NPC93670