ID: ALA504485

Max Phase: Preclinical

Molecular Formula: C41H26O26

Molecular Weight: 934.63

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  O=C1OC[C@H]2OC(=O)c3cc(O)c(O)c(O)c3-c3c(O)c(O)c(O)c4c3C(=O)O[C@H]([C@H]3OC(=O)c5c-4c(O)c(O)c(O)c5[C@H]3O)[C@@H]2OC(=O)c2cc(O)c(O)c(O)c2-c2c1cc(O)c(O)c2O

Standard InChI:  InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11-,31-,34-,35+,36+/m1/s1

Standard InChI Key:  UDYKDZHZAKSYCO-JLQXGYSZSA-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: 934.63

Molecular Weight (Monoisotopic): 934.0712

AlogP: 1.32

#Rotatable Bonds: 0

Polar Surface Area: 455.18

Molecular Species: NEUTRAL

HBA: 26

HBD: 16

#RO5 Violations: 3

HBA (Lipinski): 26

HBD (Lipinski): 16

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.87

CX Basic pKa:

CX LogP: 2.03

CX LogD: 1.03

Aromatic Rings: 5

Heavy Atoms: 67

QED Weighted: 0.06

Np Likeness Score: 0.99

References

1. 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]

2. Adamczeski M, Ni JX, Jaber H, Huang J, Kang R, Nakatsu T.  (1992)  A Novel Hydrolyzable Tannin and Related Compounds Isolated from the Leaf Surface of Chrysolepis sempervirens,  55  (4): [10.1021/np50082a024]

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. Haslam E..  (1996)  Natural polyphenols (vegetable tannins) as drugs: possible modes of action.,  59  (2): [PMID:8991956] [10.1021/np960040+]

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. Granica S,Vahjen W,Zentek J,Melzig MF,Pawłowska KA,Piwowarski JP.  (2020)  Lythrum salicaria Ellagitannins Stimulate IPEC-J2 Cells Monolayer Formation and Inhibit Enteropathogenic Escherichia coli Growth and Adhesion.,  83  (12): [PMID:33270444] [10.1021/acs.jnatprod.0c00776]

Source

Source(1):

• Scientific Literature