(-)-Epigallocatechin Gallate

ID: ALA4088244

PubChem CID: 89280670

Max Phase: Preclinical

Molecular Formula: C23H20O11

Molecular Weight: 472.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(c1)O[C@H](c1cc(O)c(O)c(O)c1)[C@H](OC(=O)c1cc(O)c(O)c(O)c1)C2

Standard InChI:  InChI=1S/C23H20O11/c1-32-11-6-13(24)12-8-19(34-23(31)10-4-16(27)21(30)17(28)5-10)22(33-18(12)7-11)9-2-14(25)20(29)15(26)3-9/h2-7,19,22,24-30H,8H2,1H3/t19-,22-/m1/s1

Standard InChI Key:  YNUCVHDPBKKFBD-DENIHFKCSA-N

Molfile:  

     RDKit          2D

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    3.7202   -5.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4282   -6.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265   -4.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1351   -4.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2596   -4.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2571   -3.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635   -3.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481   -3.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2653   -6.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2634   -6.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9714   -7.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6790   -6.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6741   -6.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9655   -5.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -5.7088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3883   -7.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9732   -8.1710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4240   -3.6853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -6.1389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3048   -5.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
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  7  8  1  0
  8  9  1  0
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  9 11  1  1
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 15 16  1  0
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 17 18  1  0
 18 19  2  0
 19 13  1  0
 18 20  1  0
 17 21  1  0
 16 22  1  0
  8 23  1  1
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 27 29  1  0
 26 30  1  0
 25 31  1  0
  4 32  1  0
  2 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088244

   [(2R,3R)-5-hydroxy-7-methoxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.40

Molecular Weight (Monoisotopic): 472.1006

AlogP: 2.54

#Rotatable Bonds: 4

Polar Surface Area: 186.37

Molecular Species: NEUTRAL

HBA: 11

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.00

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.12

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.22

Np Likeness Score: 1.46

References

1. Nasti R, Rossi D, Amadio M, Pascale A, Unver MY, Hirsch AKH, Collina S..  (2017)  Compounds Interfering with Embryonic Lethal Abnormal Vision (ELAV) Protein-RNA Complexes: An Avenue for Discovering New Drugs.,  60  (20): [PMID:28587461] [10.1021/acs.jmedchem.6b01871]

Source

Source(1):

• Scientific Literature