Epicatechin pentaacetate

Details

• Internal ID: 90726e3b-6e3d-4a47-924f-2c21ded1b6d3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: [(2R,3R)-5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-3,4-dihydro-2H-chromen-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2=C(C=C(C=C2OC(=O)C)OC(=O)C)OC1C3=CC(=C(C=C3)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1CC2=C(C=C(C=C2OC(=O)C)OC(=O)C)O[C@@H]1C3=CC(=C(C=C3)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C25H24O11/c1-12(26)31-18-9-21(33-14(3)28)19-11-24(35-16(5)30)25(36-22(19)10-18)17-6-7-20(32-13(2)27)23(8-17)34-15(4)29/h6-10,24-25H,11H2,1-5H3/t24-,25-/m1/s1
• InChI Key: BKYWAYNSDFXIPL-JWQCQUIFSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₁₁
• Molecular Weight: 500.40 g/mol
• Exact Mass: 500.13186158 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 20194-41-6
• CHEMBL2408677
• [(2R,3R)-5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-3,4-dihydro-2H-chromen-3-yl] acetate
• SR-05000002728
• SPBio_000570
• Epicatechinpentaacetate
• Epicatechol pentaacetate
• Spectrum_001964
• Spectrum2_000465
• Spectrum3_001219
• Spectrum4_001633
• Spectrum5_000445
• BSPBio_002638
• KBioGR_002065
• KBioSS_002522
• SPECTRUM1504256
• SCHEMBL14691288
• KBio2_002514
• KBio2_005082
• KBio2_007650
• KBio3_002138
• 2H-1-Benzopyran-3,5,7-triol, 2-[3,4-bis(acetyloxy)phenyl]-3,4-dihydro-, triacetate, (2R,3R)-
• BDBM50437696
• CCG-38704
• AKOS016034197
• SDCCGMLS-0066813.P001
• NCGC00178559-01
• SR-05000002728-1
• SR-05000002728-2
• BRD-K93674274-001-02-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9743	97.43%
Caco-2	-	0.6927	69.27%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6861	68.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9530	95.30%
P-glycoprotein inhibitior	+	0.9217	92.17%
P-glycoprotein substrate	-	0.8176	81.76%
CYP3A4 substrate	+	0.5875	58.75%
CYP2C9 substrate	-	0.7850	78.50%
CYP2D6 substrate	-	0.7374	73.74%
CYP3A4 inhibition	-	0.8240	82.40%
CYP2C9 inhibition	-	0.7611	76.11%
CYP2C19 inhibition	-	0.8486	84.86%
CYP2D6 inhibition	-	0.9828	98.28%
CYP1A2 inhibition	+	0.7591	75.91%
CYP2C8 inhibition	-	0.6352	63.52%
CYP inhibitory promiscuity	-	0.5432	54.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5781	57.81%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.8877	88.77%
Skin irritation	-	0.8267	82.67%
Skin corrosion	-	0.9708	97.08%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7993	79.93%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.6299	62.99%
Acute Oral Toxicity (c)	III	0.5170	51.70%
Estrogen receptor binding	+	0.8764	87.64%
Androgen receptor binding	+	0.6699	66.99%
Thyroid receptor binding	+	0.5169	51.69%
Glucocorticoid receptor binding	+	0.8637	86.37%
Aromatase binding	-	0.6829	68.29%
PPAR gamma	+	0.6704	67.04%
Honey bee toxicity	-	0.7310	73.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9705	97.05%

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	97.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.76%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.22%	86.33%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	89.75%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.06%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.41%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.31%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.62%	95.56%
CHEMBL2535	P11166	Glucose transporter	83.79%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.22%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.74%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.99%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.42%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.87%	92.62%
CHEMBL4208	P20618	Proteasome component C5	80.79%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.07%	95.89%

Plants that contains it

• Breonia chinensis
• Camellia sinensis
• Campylotropis hirtella
• Ceropegia dichotoma
• Crinum moorei
• Crotalaria candicans
• Cryptomeria japonica
• Dendrobium loddigesii
• Distephanus angulifolius
• Eucalyptus apodophylla
• Ginkgo biloba
• Glycosmis macrophylla
• Gypsophila perfoliata
• Hypericum polyanthemum
• Juniperus drupacea
• Lophostemon confertus
• Mentha × gentilis
• Ononis spinosa
• Orbivestus karaguensis
• Pentaclethra macrophylla
• Periploca sepium
• Pinalia japonica
• Plectranthus hereroensis
• Prunus padus
• Prunus persica
• Pterocaulon virgatum
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rhizophora stylosa
• Rhodiola semenovii
• Salvia sessei
• Sonneratia caseolaris
• Stephania zippeliana
• Trichilia catigua
• Veronica polita

Cross-Links

• PubChem: 5317058
• NPASS: NPC224941
• ChEMBL: CHEMBL2408677
• LOTUS: LTS0132688
• wikiData: Q104937847