2-[(4R,5S,7R,8R,11S,12S,13S,21S)-13,17,18,21-tetrahydroxy-7-(hydroxymethyl)-2,10,14-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,9,15-tetraoxatetracyclo[10.7.1.14,8.016,20]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

Details

• Internal ID: ade74fbb-db5e-4aa4-8c19-92b29e879c2c
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 2-[(4R,5S,7R,8R,11S,12S,13S,21S)-13,17,18,21-tetrahydroxy-7-(hydroxymethyl)-2,10,14-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,9,15-tetraoxatetracyclo[10.7.1.14,8.016,20]henicosa-1(19),16(20),17-trien-11-yl]acetic acid
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C(=O)OC2C3C(C(C(O2)CO)OC(=O)C(C4C(C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)CC(=O)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)OC(=O)[C@H]([C@@H]4[C@@H](C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)CC(=O)O)O
• InChI: InChI=1S/C27H24O19/c28-5-12-20-19(37)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)21-15(7)14(18(36)26(41)44-21)8(4-13(32)33)25(40)43-20/h1-3,8,12,14,18-20,22,27-31,34-37H,4-5H2,(H,32,33)/t8-,12+,14-,18-,19-,20-,22+,27-/m0/s1
• InChI Key: HPQIRFXIDGVWBA-JYJNVYNPSA-N
• Popularity: 5 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: -1.70
• 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	-	0.6483	64.83%
Caco-2	-	0.9081	90.81%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4297	42.97%
OATP2B1 inhibitior	-	0.8472	84.72%
OATP1B1 inhibitior	-	0.3360	33.60%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6061	60.61%
P-glycoprotein inhibitior	+	0.6388	63.88%
P-glycoprotein substrate	-	0.5882	58.82%
CYP3A4 substrate	+	0.6404	64.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8605	86.05%
CYP3A4 inhibition	-	0.8400	84.00%
CYP2C9 inhibition	-	0.9264	92.64%
CYP2C19 inhibition	-	0.9404	94.04%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.9381	93.81%
CYP2C8 inhibition	+	0.6316	63.16%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7188	71.88%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8769	87.69%
Skin irritation	-	0.8194	81.94%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.5108	51.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.3838	38.38%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8747	87.47%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8487	84.87%
Acute Oral Toxicity (c)	III	0.4960	49.60%
Estrogen receptor binding	+	0.7843	78.43%
Androgen receptor binding	+	0.7277	72.77%
Thyroid receptor binding	-	0.5669	56.69%
Glucocorticoid receptor binding	-	0.5832	58.32%
Aromatase binding	-	0.5158	51.58%
PPAR gamma	+	0.6436	64.36%
Honey bee toxicity	-	0.7595	75.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7599	75.99%

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	99.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.57%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.12%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.99%	95.56%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.87%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.55%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.54%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.25%	96.09%
CHEMBL3194	P02766	Transthyretin	86.63%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.32%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.29%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.79%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.85%	97.36%
CHEMBL5255	O00206	Toll-like receptor 4	82.88%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	81.85%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.47%	86.92%
CHEMBL1781	P11387	DNA topoisomerase I	80.55%	97.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.27%	96.37%

Plants that contains it

• Phyllanthus emblica
• Terminalia chebula

Cross-Links

• PubChem: 101260929
• NPASS: NPC191556