2-[(4S,5S,8R,11S,12S,13S,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-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: 7e35eee7-f34a-4185-a3b0-0045fe3744c1
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 2-[(4S,5S,8R,11S,12S,13S,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-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)OCC2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C(C(C(=O)O3)CC(=O)O)C(C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C(=O)OCC2[C@@H]3[C@@H]([C@@H]([C@@H](O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5[C@H]([C@@H](C(=O)O3)CC(=O)O)[C@@H](C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
• InChI: InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22?,24-,30-,31+,33-,34-,41-/m0/s1
• InChI Key: YGVHOSGNOYKRIH-AAYPSMFASA-N
• Popularity: 46 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₃₂O₂₇
• Molecular Weight: 956.70 g/mol
• Exact Mass: 956.11309574 g/mol
• Topological Polar Surface Area (TPSA): 447.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.02
• H-Bond Acceptor: 26
• H-Bond Donor: 13
• Rotatable Bonds: 9

Synonyms

• MLS000697665
• SMR000445569
• D0Z9YK
• CHEMBL1391063
• BDBM47828
• cid_16745534

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6426	64.26%
Caco-2	-	0.8897	88.97%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5087	50.87%
OATP2B1 inhibitior	-	0.7131	71.31%
OATP1B1 inhibitior	-	0.3814	38.14%
OATP1B3 inhibitior	+	0.9108	91.08%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8233	82.33%
P-glycoprotein inhibitior	+	0.7251	72.51%
P-glycoprotein substrate	-	0.5512	55.12%
CYP3A4 substrate	+	0.6572	65.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8599	85.99%
CYP3A4 inhibition	-	0.8325	83.25%
CYP2C9 inhibition	-	0.9030	90.30%
CYP2C19 inhibition	-	0.9331	93.31%
CYP2D6 inhibition	-	0.8961	89.61%
CYP1A2 inhibition	-	0.9314	93.14%
CYP2C8 inhibition	+	0.6486	64.86%
CYP inhibitory promiscuity	-	0.9175	91.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6899	68.99%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8909	89.09%
Skin irritation	-	0.8112	81.12%
Skin corrosion	-	0.9601	96.01%
Ames mutagenesis	-	0.5408	54.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.6605	66.05%
Micronuclear	+	0.6992	69.92%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8727	87.27%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9238	92.38%
Acute Oral Toxicity (c)	III	0.5580	55.80%
Estrogen receptor binding	+	0.7870	78.70%
Androgen receptor binding	+	0.7662	76.62%
Thyroid receptor binding	-	0.4881	48.81%
Glucocorticoid receptor binding	-	0.5053	50.53%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7088	70.88%
Honey bee toxicity	-	0.7903	79.03%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8545	85.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	112.2 nM; 112.2 nM; 446.7 nM	Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	100 nM; 100 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	177.8 nM; 177.8 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	2.2 nM; 2.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	28183.8 nM	Potency	via CMAUP
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	1522.67 nM	IC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	707.9 nM; 707.9 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	1572.8 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	112.2 nM; 112.2 nM; 112.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	44668.4 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	31.6 nM; 31.6 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	891.3 nM; 891.3 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.95%	91.49%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	95.55%	83.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.74%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.11%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.46%	99.17%
CHEMBL2581	P07339	Cathepsin D	88.83%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.04%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.77%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.52%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.50%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	86.41%	92.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.09%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.36%	89.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.74%	94.42%
CHEMBL3194	P02766	Transthyretin	84.40%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	84.38%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	83.34%	91.19%
CHEMBL3891	P07384	Calpain 1	82.41%	93.04%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.85%	80.78%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.78%	89.34%

Plants that contains it

• Phyllanthus emblica
• Terminalia bellirica
• Terminalia chebula

Cross-Links

• PubChem: 16745534
• NPASS: NPC7839
• ChEMBL: CHEMBL1391063