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

ID: ALA447974

Chembl Id: CHEMBL447974

Cas Number: 79886-49-0

PubChem CID: 440308

Max Phase: Preclinical

Molecular Formula: C27H24O18

Molecular Weight: 636.47

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

Standard InChI:  InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)22(38)23(44-25(40)9-3-13(30)19(35)14(31)4-9)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2/t17-,21-,22+,23-,27+/m1/s1

Standard InChI Key:  LLENXGNWVNSBQG-VFTFQOQOSA-N

Alternative Forms

1. Parent:

   

   ALA447974

   1,2,6-Trigalloylglucose

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: 636.47

Molecular Weight (Monoisotopic): 636.0963

AlogP: -0.28

#Rotatable Bonds: 7

Polar Surface Area: 310.66

Molecular Species: NEUTRAL

HBA: 18

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.67

CX Basic pKa: ┄

CX LogP: 1.82

CX LogD: 1.59

Aromatic Rings: 3

Heavy Atoms: 45

QED Weighted: 0.09

Np Likeness Score: 1.08

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. Duan D, Li Z, Luo H, Zhang W, Chen L, Xu X..  (2004)  Antiviral compounds from traditional Chinese medicines Galla Chinese as inhibitors of HCV NS3 protease.,  14  (24): [PMID:15546725] [10.1016/j.bmcl.2004.09.067]

4. Kim HJ, Woo ER, Shin CG, Park H..  (1998)  A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.,  61  (1): [PMID:9461665] [10.1021/np970171q]

5. Abe I, Kashiwagi Y, Noguchi H, Tanaka T, Ikeshiro Y, Kashiwada Y..  (2001)  Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase.,  64  (8): [PMID:11520216] [10.1021/np010100y]

6. 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]

7. Bokesch HR, Wamiru A, Le Grice SF, Beutler JA, McKee TC, McMahon JB..  (2008)  HIV-1 ribonuclease H inhibitory phenolic glycosides from Eugenia hyemalis.,  71  (9): [PMID:18763827] [10.1021/np8002518]

8. Nyamboki DK, Bedane KG, Hassan K, Brieger L, Strohmann C, Spiteller M, Matasyoh JC..  (2021)  Cytotoxic Compounds from the Stem Bark of Two subsp. of Bersama abyssinica.,  84  (5.0): [PMID:33974421] [10.1021/acs.jnatprod.0c01141]

Source

Source(1):

• Scientific Literature