2-[(4R,5S,7R,8R,9S,12S,13S,14S)-8,14,18,19-tetrahydroxy-7-(hydroxymethyl)-2,11,15-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,10,16-tetraoxatetracyclo[11.7.1.04,9.017,21]henicosa-1(20),17(21),18-trien-12-yl]acetic acid

Details

• Internal ID: bfab8528-1f52-466a-b951-0875621c35d6
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 2-[(4R,5S,7R,8R,9S,12S,13S,14S)-8,14,18,19-tetrahydroxy-7-(hydroxymethyl)-2,11,15-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,10,16-tetraoxatetracyclo[11.7.1.04,9.017,21]henicosa-1(20),17(21),18-trien-12-yl]acetic acid
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C(=O)OC2C3C(C(C(O2)CO)O)OC(=O)C(C4C(C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)CC(=O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C(=O)O[C@H]2[C@H]3[C@H]([C@@H]([C@H](O2)CO)O)OC(=O)[C@H]([C@@H]4[C@@H](C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)CC(=O)O
• InChI: InChI=1S/C27H24O19/c28-5-12-18(36)21-22(27(42-12)46-23(38)6-1-9(29)16(34)10(30)2-6)45-24(39)7-3-11(31)17(35)20-15(7)14(19(37)26(41)43-20)8(4-13(32)33)25(40)44-21/h1-3,8,12,14,18-19,21-22,27-31,34-37H,4-5H2,(H,32,33)/t8-,12+,14-,18+,19-,21-,22+,27-/m0/s1
• InChI Key: DHIUETZAWAZMBO-WXAXTOTNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₉
• Molecular Weight: 652.50 g/mol
• Exact Mass: 652.09117853 g/mol
• Topological Polar Surface Area (TPSA): 314.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.95
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6430	64.30%
Caco-2	-	0.9031	90.31%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Nucleus	0.4695	46.95%
OATP2B1 inhibitior	-	0.8456	84.56%
OATP1B1 inhibitior	-	0.3548	35.48%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6387	63.87%
P-glycoprotein inhibitior	+	0.6204	62.04%
P-glycoprotein substrate	-	0.5931	59.31%
CYP3A4 substrate	+	0.6384	63.84%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.9062	90.62%
CYP2C9 inhibition	-	0.9617	96.17%
CYP2C19 inhibition	-	0.9470	94.70%
CYP2D6 inhibition	-	0.9416	94.16%
CYP1A2 inhibition	-	0.9442	94.42%
CYP2C8 inhibition	+	0.6025	60.25%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7212	72.12%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8787	87.87%
Skin irritation	-	0.8230	82.30%
Skin corrosion	-	0.9644	96.44%
Ames mutagenesis	-	0.5162	51.62%
Human Ether-a-go-go-Related Gene inhibition	+	0.6628	66.28%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8891	88.91%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8489	84.89%
Acute Oral Toxicity (c)	III	0.4701	47.01%
Estrogen receptor binding	+	0.7907	79.07%
Androgen receptor binding	+	0.7201	72.01%
Thyroid receptor binding	-	0.5646	56.46%
Glucocorticoid receptor binding	-	0.6238	62.38%
Aromatase binding	-	0.5679	56.79%
PPAR gamma	+	0.6150	61.50%
Honey bee toxicity	-	0.7784	77.84%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7770	77.70%

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	99.39%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.60%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	89.50%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.52%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.54%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.51%	96.09%
CHEMBL3194	P02766	Transthyretin	86.52%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.48%	89.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.86%	83.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.71%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.29%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	82.96%	94.73%
CHEMBL1781	P11387	DNA topoisomerase I	82.22%	97.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.74%	92.50%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.20%	96.37%

Plants that contains it

• Acalypha indica

Cross-Links

• PubChem: 163188905
• LOTUS: LTS0206625
• wikiData: Q104980205