theograndin I

Details

• Internal ID: c4fa2650-9b05-42e2-8ed3-3b5a9f4cab42
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-8-O-glucuronides
• IUPAC Name: (2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy-3,5-dihydroxy-4-sulfooxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)OC4C(C(C(C(O4)C(=O)O)O)OS(=O)(=O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)OS(=O)(=O)O)O)O
• InChI: InChI=1S/C21H18O15S/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)16(17(13)33-12)34-21-15(27)18(36-37(30,31)32)14(26)19(35-21)20(28)29/h1-6,14-15,18-19,21-23,25-27H,(H,28,29)(H,30,31,32)/t14-,15+,18-,19-,21+/m0/s1
• InChI Key: RUJCBFMBNQPWBK-DLSLMLROSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₁₅S
• Molecular Weight: 542.40 g/mol
• Exact Mass: 542.03664104 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.33
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• H7Z3V79EXC
• (2S,3R,4S,5R,6S)-6-((5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl)oxy)-3,5-dihydroxy-4-(sulfooxy)oxane-2-carboxylic acid
• 637004-62-7
• Isoscutellarein 8-o-beta-D-glucuronide 3''-O-sulfate
• Isoscutellarein 8-O-beta-D-glucuronopyranoside 3''-O-sulfate
• beta-D-Glucopyranosiduronic acid, 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-8-yl, 3-(hydrogen sulfate)
• UNII-H7Z3V79EXC
• CHEMBL460972
• DTXSID801045348
• Q15427882
• ISOSCUTELLAREIN 8-O-.BETA.-D-GLUCURONIDE 3''-O-SULFATE
• ISOSCUTELLAREIN 8-O-.BETA.-D-GLUCURONOPYRANOSIDE 3''-O-SULFATE
• (2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy-3,5-dihydroxy-4-sulfooxyoxane-2-carboxylic acid
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-8-YL, 3-(HYDROGEN SULFATE)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6822	68.22%
Caco-2	-	0.9033	90.33%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4638	46.38%
OATP2B1 inhibitior	+	0.5960	59.60%
OATP1B1 inhibitior	+	0.8901	89.01%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5407	54.07%
P-glycoprotein inhibitior	-	0.5612	56.12%
P-glycoprotein substrate	-	0.7403	74.03%
CYP3A4 substrate	+	0.6226	62.26%
CYP2C9 substrate	-	0.8066	80.66%
CYP2D6 substrate	-	0.8758	87.58%
CYP3A4 inhibition	-	0.9198	91.98%
CYP2C9 inhibition	-	0.8031	80.31%
CYP2C19 inhibition	-	0.8546	85.46%
CYP2D6 inhibition	-	0.9025	90.25%
CYP1A2 inhibition	-	0.7109	71.09%
CYP2C8 inhibition	+	0.7517	75.17%
CYP inhibitory promiscuity	-	0.8608	86.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5304	53.04%
Carcinogenicity (trinary)	Non-required	0.6553	65.53%
Eye corrosion	-	0.9436	94.36%
Eye irritation	-	0.8300	83.00%
Skin irritation	-	0.7573	75.73%
Skin corrosion	-	0.8430	84.30%
Ames mutagenesis	-	0.5754	57.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5291	52.91%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6238	62.38%
skin sensitisation	-	0.8421	84.21%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9388	93.88%
Acute Oral Toxicity (c)	III	0.6142	61.42%
Estrogen receptor binding	+	0.6011	60.11%
Androgen receptor binding	+	0.8418	84.18%
Thyroid receptor binding	-	0.5596	55.96%
Glucocorticoid receptor binding	-	0.5449	54.49%
Aromatase binding	-	0.6168	61.68%
PPAR gamma	+	0.6027	60.27%
Honey bee toxicity	-	0.6903	69.03%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9869	98.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.95%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.21%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.66%	98.95%
CHEMBL3194	P02766	Transthyretin	94.90%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.63%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.33%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.82%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.19%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.22%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.43%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	84.56%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.18%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.02%	91.19%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.58%	97.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.56%	99.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.83%	85.31%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.45%	89.23%
CHEMBL242	Q92731	Estrogen receptor beta	80.10%	98.35%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.09%	83.57%

Plants that contains it

• Cosmos sulphureus
• Ophiopogon japonicus
• Roemeria hispida
• Tanacetum argenteum
• Thamnosma rhodesica
• Theobroma grandiflorum

Cross-Links

• PubChem: 11156985
• NPASS: NPC222674
• LOTUS: LTS0077352
• wikiData: Q15427882