CID 250397

Details

• Internal ID: 973d92f9-758e-4955-bd0e-7067598c31fa
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 2-[13,14,15,18,19,20,31,35,36-nonahydroxy-2,10,23,28,32-pentaoxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,9,24,27,33-hexaoxaheptacyclo[28.7.1.04,25.07,26.011,16.017,22.034,38]octatriaconta-1(37),11,13,15,17,19,21,34(38),35-nonaen-29-yl]acetic acid
• SMILES (Canonical): C1C2C3C(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(=C7C8=C(C(=C(C=C8C(=O)O1)O)O)O)O)O)O
• SMILES (Isomeric): C1C2C3C(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(=C7C8=C(C(=C(C=C8C(=O)O1)O)O)O)O)O)O
• InChI: InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)
• InChI Key: HGJXAVROWQLCTP-UHFFFAOYSA-N
• Popularity: 74 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₃₀O₂₇
• Molecular Weight: 954.70 g/mol
• Exact Mass: 954.09744568 g/mol
• Topological Polar Surface Area (TPSA): 447.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.00
• H-Bond Acceptor: 26
• H-Bond Donor: 13
• Rotatable Bonds: 4

Synonyms

• 23094-71-5
• NSC342674
• 2-[13,14,15,18,19,20,31,35,36-Nonahydroxy-2,10,23,28,32-pentaoxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,9,24,27,33-hexaoxaheptacyclo[28.7.1.04,25.07,26.011,16.017,22.034,38]octatriaconta-1(37),11,13,15,17,19,21,34(38),35-nonaen-29-yl]acetic acid
• Chebu-lagic acid
• .beta.-D-Glucopyranose,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl)butanedioic acid, cyclic 3,3-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 1-(3,4,5-trihydroxybenzoate)
• SCHEMBL1877153
• CHEMBL1970427
• BDBM512895
• DTXSID401026980
• HY-N1996
• NSC69863
• NSC-69863
• CS-5820
• NCI60_003043
• FT-0698058
• .beta.-D-Glucopyranose,4-dihydro-3,7,8-trihydroxy-2-oxo-2H-1-benzopyran-4-yl)butanedioic acid, cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'dicarboxylate) 1-(3,4,5-trihydroxybenzoate)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6426	64.26%
Caco-2	-	0.8910	89.10%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5087	50.87%
OATP2B1 inhibitior	-	0.7123	71.23%
OATP1B1 inhibitior	+	0.7223	72.23%
OATP1B3 inhibitior	+	0.9108	91.08%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8609	86.09%
P-glycoprotein inhibitior	+	0.7208	72.08%
P-glycoprotein substrate	+	0.5887	58.87%
CYP3A4 substrate	+	0.6691	66.91%
CYP2C9 substrate	-	0.8026	80.26%
CYP2D6 substrate	-	0.8611	86.11%
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	+	0.7192	71.92%
CYP inhibitory promiscuity	-	0.9175	91.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6899	68.99%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8902	89.02%
Skin irritation	-	0.8112	81.12%
Skin corrosion	-	0.9601	96.01%
Ames mutagenesis	-	0.5208	52.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.7139	71.39%
Micronuclear	+	0.6992	69.92%
Hepatotoxicity	-	0.5750	57.50%
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	-	0.8644	86.44%
Acute Oral Toxicity (c)	III	0.5580	55.80%
Estrogen receptor binding	+	0.8044	80.44%
Androgen receptor binding	+	0.7622	76.22%
Thyroid receptor binding	-	0.4921	49.21%
Glucocorticoid receptor binding	-	0.5165	51.65%
Aromatase binding	-	0.4943	49.43%
PPAR gamma	+	0.7047	70.47%
Honey bee toxicity	-	0.7639	76.39%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8545	85.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1781	P11387	DNA topoisomerase I	50 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.08%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.94%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.60%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.44%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.29%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.74%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.67%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.92%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.23%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.06%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.51%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.68%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.21%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.96%	91.71%
CHEMBL340	P08684	Cytochrome P450 3A4	84.42%	91.19%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.21%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.98%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.26%	97.21%
CHEMBL3194	P02766	Transthyretin	82.22%	90.71%

Plants that contains it

• Acalypha indica
• Caryocar villosum
• Cunonia macrophylla
• Erodium stephanianum
• Euphorbia humifusa
• Euphorbia makinoi
• Euphorbia nutans
• Euphorbia watanabei
• Excoecaria agallocha
• Excoecaria kawakamii
• Lumnitzera racemosa
• Macaranga sinensis
• Phyllanthus emblica
• Phyllanthus flexuosus
• Terminalia bellirica
• Terminalia catappa
• Terminalia chebula
• Terminalia citrina
• Vernicia fordii

Cross-Links

• PubChem: 250397
• NPASS: NPC173872
• LOTUS: LTS0074486
• wikiData: Q103785778