ID: ALA525240

Max Phase: Preclinical

Molecular Formula: C41H30O27

Molecular Weight: 954.66

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)C[C@@H]1C(=O)O[C@H]2[C@@H]3OC(=O)c4cc(O)c(O)c(O)c4-c4c(cc(O)c(O)c4O)C(=O)OC[C@H]2O[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H]3OC(=O)c2cc(O)c(O)c3c2[C@H]1[C@H](O)C(=O)O3

Standard InChI:  InChI=1S/C41H30O27/c42-13-1-8(2-14(43)24(13)49)35(56)68-41-34-33-31(64-39(60)12(6-19(47)48)22-23-11(38(59)67-34)5-17(46)27(52)32(23)65-40(61)30(22)55)18(63-41)7-62-36(57)9-3-15(44)25(50)28(53)20(9)21-10(37(58)66-33)4-16(45)26(51)29(21)54/h1-5,12,18,22,30-31,33-34,41-46,49-55H,6-7H2,(H,47,48)/t12-,18+,22-,30-,31+,33-,34+,41-/m0/s1

Standard InChI Key:  HGJXAVROWQLCTP-YABCKIEDSA-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: 954.66

Molecular Weight (Monoisotopic): 954.0974

AlogP: 0.00

#Rotatable Bonds: 4

Polar Surface Area: 447.09

Molecular Species: ACID

HBA: 26

HBD: 13

#RO5 Violations: 3

HBA (Lipinski): 27

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.15

CX Basic pKa:

CX LogP: 2.30

CX LogD: -1.77

Aromatic Rings: 4

Heavy Atoms: 68

QED Weighted: 0.06

Np Likeness Score: 1.49

References

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2. 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]

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4. Li XC, Joshi AS, ElSohly HN, Khan SI, Jacob MR, Zhang Z, Khan IA, Ferreira D, Walker LA, Broedel SE, Raulli RE, Cihlar RL..  (2002)  Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.,  65  (12): [PMID:12502337] [10.1021/np020289t]

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7. Hecht SM, Berry DE, MacKenzie LJ, Busby RW, Nasuti CA..  (1992)  A strategy for identifying novel, mechanistically unique inhibitors of topoisomerase I.,  55  (4): [PMID:1324981] [10.1021/np50082a001]

8. 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]

9. Zhang YJ, Abe T, Tanaka T, Yang CR, Kouno I..  (2001)  Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica.,  64  (12): [PMID:11754604] [10.1021/np010370g]

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

11. Li Y, Yu S, Liu D, Proksch P, Lin W..  (2012)  Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L.,  22  (2): [PMID:22196120] [10.1016/j.bmcl.2011.11.109]

12. Fogliani B, Raharivelomanana P, Bianchini JP, Bouraïma-Madjèbi S, Hnawia E..  (2005)  Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia.,  66  (2): [PMID:15652581] [10.1016/j.phytochem.2004.11.016]

13. Gilda Padalino, Avril Coghlan, Giampaolo Pagliuca, Josephine F. Thomas, Matthew Berriman, Karl F. Hoffmann.  (2023)  Using ChEMBL to complement schistosome drug discovery,  [10.6019/CHEMBL5096127]

14. S AH, Pujar GV, Sethu AK, Bhagyalalitha M, Singh M..  (2021)  Dengue structural proteins as antiviral drug targets: Current status in the drug discovery & development.,  221  [PMID:34020338] [10.1016/j.ejmech.2021.113527]

Source

Source(2):

• Scientific Literature
• Cardiff Schistosomiasis Dataset 2023