7,7,8,12,13,22-hexahydroxy-21-hydroxymethyl-3,6,16-trioxo-19-(3,4,5-trihydroxyphenylcarbonyloxy)-2,17,20,23-tetraoxapentacyclo[16.3.1.18,11.04,9.010,15]tricosa-4,10,12,14-tetraene

ID: ALA447361

Chembl Id: CHEMBL447361

PubChem CID: 10416810

Max Phase: Preclinical

Molecular Formula: C27H22O19

Molecular Weight: 650.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Furosin | Furosin|CHEMBL447361|BDBM50377924|[(1S,9R,18R,19S,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.18,11.04,9.010,15]tricosa-4,10,12,14-tetraen-19-yl] 3,4,5-trihydroxybenzoate

Canonical SMILES:  O=C1O[C@H]2[C@H](O)[C@@H](OC(=O)c3cc(O)c(O)c4c3[C@@H]3C1=CC(=O)C(O)(O)C3(O)O4)[C@H](OC(=O)c1cc(O)c(O)c(O)c1)O[C@@H]2CO

Standard InChI:  InChI=1S/C27H22O19/c28-5-12-19-18(35)21(25(42-12)45-22(36)6-1-9(29)16(33)10(30)2-6)44-23(37)7-3-11(31)17(34)20-14(7)15-8(24(38)43-19)4-13(32)26(39,40)27(15,41)46-20/h1-4,12,15,18-19,21,25,28-31,33-35,39-41H,5H2/t12-,15+,18+,19-,21-,25+,27?/m1/s1

Standard InChI Key:  CXTMLIMZRPKULL-YXYYPBJFSA-N

Alternative Forms

1. Parent:

   

   ALA447361

   FUROSIN

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: 650.45

Molecular Weight (Monoisotopic): 650.0755

AlogP: -3.04

#Rotatable Bonds: 3

Polar Surface Area: 316.73

Molecular Species: NEUTRAL

HBA: 19

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.80

CX Basic pKa: ┄

CX LogP: -0.24

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.07

Np Likeness Score: 2.22

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. 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. 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. 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]

5. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays