(E)-3-[4-hydroxy-3-methoxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,5-dien-1-yl]prop-2-enoic acid

Details

• Internal ID: d69ccf14-4004-4003-a267-1f362f7c95fd
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > C-glycosyl compounds
• IUPAC Name: (E)-3-[4-hydroxy-3-methoxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,5-dien-1-yl]prop-2-enoic acid
• SMILES (Canonical): COC1C=C(C=CC1(C2C(C(C(C(O2)CO)O)O)O)O)C=CC(=O)O
• SMILES (Isomeric): COC1C=C(C=CC1([C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)/C=C/C(=O)O
• InChI: InChI=1S/C16H22O9/c1-24-10-6-8(2-3-11(18)19)4-5-16(10,23)15-14(22)13(21)12(20)9(7-17)25-15/h2-6,9-10,12-15,17,20-23H,7H2,1H3,(H,18,19)/b3-2+/t9-,10?,12-,13+,14-,15-,16?/m1/s1
• InChI Key: HHVMYMLXWNPMAF-UZZNNUGYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₉
• Molecular Weight: 358.34 g/mol
• Exact Mass: 358.12638228 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.29
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6001	60.01%
Caco-2	-	0.8433	84.33%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8376	83.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8604	86.04%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7393	73.93%
P-glycoprotein inhibitior	-	0.8839	88.39%
P-glycoprotein substrate	-	0.8004	80.04%
CYP3A4 substrate	+	0.6001	60.01%
CYP2C9 substrate	-	0.8015	80.15%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.9715	97.15%
CYP2C9 inhibition	-	0.8327	83.27%
CYP2C19 inhibition	-	0.8115	81.15%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	-	0.8880	88.80%
CYP2C8 inhibition	-	0.6585	65.85%
CYP inhibitory promiscuity	-	0.7220	72.20%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6997	69.97%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9664	96.64%
Skin irritation	-	0.8167	81.67%
Skin corrosion	-	0.9537	95.37%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5880	58.80%
Micronuclear	-	0.6241	62.41%
Hepatotoxicity	-	0.8266	82.66%
skin sensitisation	-	0.8655	86.55%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5501	55.01%
Estrogen receptor binding	+	0.6090	60.90%
Androgen receptor binding	+	0.5631	56.31%
Thyroid receptor binding	-	0.5135	51.35%
Glucocorticoid receptor binding	+	0.6668	66.68%
Aromatase binding	+	0.5776	57.76%
PPAR gamma	+	0.5376	53.76%
Honey bee toxicity	-	0.8577	85.77%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	-	0.5601	56.01%

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	97.31%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.28%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.90%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.19%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.05%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	87.46%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	86.28%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%

Plants that contains it

• Aristolochia foveolata

Cross-Links

• PubChem: 163185289
• LOTUS: LTS0159398
• wikiData: Q105028617