3,4,5-trihydroxy-2-(3,4,5-trihydroxyphenylcarbonyloxy)-6-(3,4,5-trihydroxyphenylcarbonyloxymethyl)tetrahydro-2H-pyran

ID: ALA522251

Chembl Id: CHEMBL522251

Cas Number: 23363-08-8

PubChem CID: 440221

Max Phase: Preclinical

Molecular Formula: C20H20O14

Molecular Weight: 484.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H](O)[C@@H](O)[C@@H]1O)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C20H20O14/c21-8-1-6(2-9(22)13(8)25)18(30)32-5-12-15(27)16(28)17(29)20(33-12)34-19(31)7-3-10(23)14(26)11(24)4-7/h1-4,12,15-17,20-29H,5H2/t12-,15-,16+,17-,20+/m1/s1

Standard InChI Key:  LYGRISUQIZNHGM-IVABAYMNSA-N

Alternative Forms

1. Parent:

   

   ALA522251

   1,6-bis-O-galloyl-beta-D-glucose

Molecule Features

Natural Product: Yes

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: 484.37

Molecular Weight (Monoisotopic): 484.0853

AlogP: -1.26

#Rotatable Bonds: 5

Polar Surface Area: 243.90

Molecular Species: NEUTRAL

HBA: 14

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.79

CX Basic pKa:

CX LogP: 0.24

CX LogD: 0.08

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.18

Np Likeness Score: 1.34

References

1. Kilkuskie RE, Kashiwada Y, Nonaka G, Nishioka I, Bodner AJ, Cheng Y, Lee K.  (1992)  HIV and reverse transcriptase inhibition by tannins,  2  (12): [10.1016/S0960-894X(00)80422-9]

2. Kashiwada Y, Nonaka G, Nishioka I, Ballas LM, Jiang JB, Janzen WP, Lee K.  (1992)  Tannins as selective inhibitors of protein kinase C,  2  (3): [10.1016/S0960-894X(01)81072-6]

3. Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH..  (1992)  Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.,  55  (8): [PMID:1431932] [10.1021/np50086a002]

4.  (2017)  Synaptojanin-2 inhibitors for use in the treatment of cancer, 

5.  (2015)  Synaptojanin-2 inhibitors and uses thereof, 

6.  (2017)  Methods of preventing tumor metastasis, treating and prognosing cancer and identifying agents which are putative metastasis inhibitors, 

7. Al Zahrani NA, El-Shishtawy RM, Asiri AM..  (2020)  Recent developments of gallic acid derivatives and their hybrids in medicinal chemistry: A review.,  204  [PMID:32731188] [10.1016/j.ejmech.2020.112609]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data