3,4,5-Trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: 24b9d142-67d6-46b6-a780-0c6c43e7b97b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-7-O-glucuronides
• IUPAC Name: 3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
• InChI: InChI=1S/C21H18O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)
• InChI Key: JBFOLLJCGUCDQP-UHFFFAOYSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₁₁
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.08491139 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.14
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid
• apigenin-7-o-glucuronide
• NSC622811
• Apigenin 7-O-|A-glucuronide
• CHEMBL1980748
• SCHEMBL12955450
• CHEBI:182306
• BCP10282
• NSC-622811
• NCI60_006773
• Apigenin 7-glucuronide pound>>Apigenin 7-O-b-glucuronide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6796	67.96%
Caco-2	-	0.9113	91.13%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6448	64.48%
OATP2B1 inhibitior	+	0.5043	50.43%
OATP1B1 inhibitior	+	0.9577	95.77%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4672	46.72%
P-glycoprotein inhibitior	-	0.7489	74.89%
P-glycoprotein substrate	-	0.9188	91.88%
CYP3A4 substrate	+	0.5603	56.03%
CYP2C9 substrate	-	0.8160	81.60%
CYP2D6 substrate	-	0.8805	88.05%
CYP3A4 inhibition	-	0.6463	64.63%
CYP2C9 inhibition	-	0.7998	79.98%
CYP2C19 inhibition	-	0.8841	88.41%
CYP2D6 inhibition	-	0.9593	95.93%
CYP1A2 inhibition	-	0.8637	86.37%
CYP2C8 inhibition	+	0.8507	85.07%
CYP inhibitory promiscuity	-	0.8219	82.19%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6094	60.94%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.8413	84.13%
Skin irritation	-	0.6406	64.06%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6067	60.67%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.7282	72.82%
skin sensitisation	-	0.9042	90.42%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8438	84.38%
Acute Oral Toxicity (c)	III	0.4015	40.15%
Estrogen receptor binding	+	0.7390	73.90%
Androgen receptor binding	+	0.7644	76.44%
Thyroid receptor binding	-	0.5144	51.44%
Glucocorticoid receptor binding	+	0.6630	66.30%
Aromatase binding	+	0.5303	53.03%
PPAR gamma	+	0.7230	72.30%
Honey bee toxicity	-	0.7439	74.39%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9464	94.64%

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	98.81%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.96%	91.49%
CHEMBL3194	P02766	Transthyretin	96.44%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.10%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.69%	99.15%
CHEMBL2581	P07339	Cathepsin D	93.36%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.67%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.73%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.85%	91.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.46%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.56%	95.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.05%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.02%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.42%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.18%	83.57%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	85.03%	89.23%
CHEMBL3401	O75469	Pregnane X receptor	84.79%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.81%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.09%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.51%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.35%	95.89%

Plants that contains it

• Acanthus ebracteatus
• Agrimonia eupatoria
• Antirrhinum majus
• Aster koraiensis
• Bellis perennis
• Collinsonia japonica
• Crotalaria juncea
• Erigeron annuus
• Fernandoa adenophylla
• Glechoma hederacea
• Hyssopus officinalis
• Inulanthera nuda
• Leucanthemum vulgare
• Medicago sativa
• Medicago truncatula
• Meehania fargesii
• Meehania urticifolia
• Millingtonia hortensis
• Monarda punctata
• Ocimum tenuiflorum
• Onopordum illyricum
• Pedicularis longiflora
• Salvia fruticosa
• Scutellaria alpina
• Scutellaria galericulata
• Scutellaria indica
• Scutellaria phyllostachya
• Sonchus erzincanicus
• Tanacetum parthenium
• Veronica spicata

Cross-Links

• PubChem: 5387370
• LOTUS: LTS0010135
• wikiData: Q104667549