ID: ALA506814

Max Phase: Preclinical

Molecular Formula: C48H28O30

Molecular Weight: 1084.72

Molecule Type: Small molecule

Representations

Synonyms (1): Punicalagin
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1O[C@@H]2[C@@H](OC(=O)c3cc(O)c(O)c(O)c3-c3c1cc(O)c(O)c3O)[C@H](O)O[C@@H]1COC(=O)c3cc(O)c(O)c(O)c3-c3c(O)c(O)c4oc(=O)c5c(c(O)c(O)c6oc(=O)c3c4c65)-c3c(cc(O)c(O)c3O)C(=O)O[C@@H]21

Standard InChI:  InChI=1S/C48H28O30/c49-10-1-6-17(31(59)27(10)55)19-23-21-22-24(47(70)76-38(21)35(63)33(19)61)20(34(62)36(64)39(22)75-46(23)69)18-9(4-13(52)28(56)32(18)60)43(66)74-37-14(5-72-42(6)65)73-48(71)41-40(37)77-44(67)7-2-11(50)25(53)29(57)15(7)16-8(45(68)78-41)3-12(51)26(54)30(16)58/h1-4,14,37,40-41,48-64,71H,5H2/t14-,37-,40+,41-,48-/m1/s1

Standard InChI Key:  ZJVUMAFASBFUBG-RILGRMFESA-N

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

Properties

Molecular Weight: 1084.72

Molecular Weight (Monoisotopic): 1084.0665

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Nonaka G, Nishioka I, Nishizawa M, Yamagishi T, Kashiwada Y, Dutschman GE, Bodner AJ, Kilkuskie RE, Cheng YC, Lee KH..  (1990)  Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells.,  53  (3): [PMID:1698933] [10.1021/np50069a008]

2. 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]

3. Kakiuchi N, Hattori M, Namba T, Nishizawa M, Yamagishi T, Okuda T..  (1985)  Inhibitory effect of tannins on reverse transcriptase from RNA tumor virus.,  48  (4): [PMID:2413172] [10.1021/np50040a016]

4. 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]

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

6. Conrad J, Vogler B, Reeb S, Klaiber I, Papajewski S, Roos G, Vasquez E, Setzer MC, Kraus W..  (2001)  Isoterchebulin and 4,6-O-isoterchebuloyl-D-glucose, novel hydrolyzable tannins from Terminalia macroptera.,  64  (3): [PMID:11277742] [10.1021/np000506v]

7. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

8. Park SH, Yang EJ, Kim SI, Song KS..  (2014)  β-Secretase (BACE1)-inhibiting C-methylrotenoids from Abronia nana suspension cultures.,  24  (13): [PMID:24835197] [10.1016/j.bmcl.2014.04.060]

9. Gau J, Prévost M, Van Antwerpen P, Sarosi MB, Rodewald S, Arnhold J, Flemmig J..  (2017)  Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.,  80  (5): [PMID:28368593] [10.1021/acs.jnatprod.6b00915]

Source

Source(1):

• Scientific Literature