TANNIN analogue

ID: ALA500292

Chembl Id: CHEMBL500292

PubChem CID: 13888120

Max Phase: Preclinical

Molecular Formula: C34H28O22

Molecular Weight: 788.58

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C34H28O22/c35-14-1-10(2-15(36)23(14)43)30(47)52-9-22-27(54-31(48)11-3-16(37)24(44)17(38)4-11)28(55-32(49)12-5-18(39)25(45)19(40)6-12)29(34(51)53-22)56-33(50)13-7-20(41)26(46)21(42)8-13/h1-8,22,27-29,34-46,51H,9H2/t22-,27-,28+,29-,34-/m1/s1

Standard InChI Key:  RJINLRBSXMOGAQ-UEKZKNBCSA-N

Alternative Forms

1. Parent:

   

   ALA500292

   galloyl(-2)[galloyl(-3)][galloyl(-4)][galloyl(-6)]b-Glc

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: 788.58

Molecular Weight (Monoisotopic): 788.1072

AlogP: 0.70

#Rotatable Bonds: 9

Polar Surface Area: 377.42

Molecular Species: NEUTRAL

HBA: 22

HBD: 13

#RO5 Violations: 3

HBA (Lipinski): 22

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.55

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 3.11

Aromatic Rings: 4

Heavy Atoms: 56

QED Weighted: 0.06

Np Likeness Score: 0.75

References

1. 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]

2. 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]

3. Lin T, Hsu F, Cheng J.  (1993)  Antihypertensive Activity of Corilagin and Chebulinic Acid, Tannins from Lumnitzera, racemosa,  56  (4): [10.1021/np50094a030]

4. Abdel-Mageed WM, Bayoumi SA, Chen C, Vavricka CJ, Li L, Malik A, Dai H, Song F, Wang L, Zhang J, Gao GF, Lv Y, Liu L, Liu X, Sayed HM, Zhang L..  (2014)  Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.,  22  (7): [PMID:24613627] [10.1016/j.bmc.2014.02.014]

Source

Source(1):

• Scientific Literature