(1R,6S,7R,11bR,1'R,6'S,7'R,11'bR)-1,7,1',7'-Tetrakis-(4-hydroxy-phenyl)-1,6,7,11b,1',6',7',11'b-octahydro-[6,6']bi[2-oxa-dibenzo[cd,h]azulenyl]-4,8,10,4',8',10'-hexaol

ID: ALA384120

Chembl Id: CHEMBL384120

PubChem CID: 44334030

Max Phase: Preclinical

Molecular Formula: C56H42O12

Molecular Weight: 906.94

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-Hopeaphenol | (-)-Hopeaphenol|Hopeaphenol|CHEMBL384120|NSC-661748|SCHEMBL14255847|DTXSID801029736|BDBM50362641|(1R,1'R,6S,6'S,7R,7'R,11bR,11'bR)-1,1',6,6',7,7',11b,11'b-Octahydro-1,1',7,7'-tetrakis(4-hydroxyphenyl)[6,6'-bibenzo[6,7]cyclohepta[1,2,3-cd]benzofuran]-4,4',8,8',10,10'-hexol|[6,6'-Bibenzo[6,7]cyclohepta[1,2,3-cd]benzofuran]-4,4',8,8',10,10'-hexol, 1,1',6,6',7,7',11b,11'b-octahydro-1,1',7,7'-tetrakis(4-hydroxyphenyl)-, [1alpha,6beta(1'R*,6'S*,7'R*,11'R*),7alpha,11balpha]-(-)-|[6,6'Show More⌵

Canonical SMILES:  Oc1ccc([C@@H]2c3c(O)cc(O)cc3[C@@H]3c4c(cc(O)cc4[C@H]2[C@@H]2c4cc(O)cc5c4[C@@H](c4cc(O)cc(O)c4[C@H]2c2ccc(O)cc2)[C@H](c2ccc(O)cc2)O5)O[C@H]3c2ccc(O)cc2)cc1

Standard InChI:  InChI=1S/C56H42O12/c57-29-9-1-25(2-10-29)45-47-37(17-33(61)21-41(47)65)53-49-39(19-35(63)23-43(49)67-55(53)27-5-13-31(59)14-6-27)51(45)52-40-20-36(64)24-44-50(40)54(56(68-44)28-7-15-32(60)16-8-28)38-18-34(62)22-42(66)48(38)46(52)26-3-11-30(58)12-4-26/h1-24,45-46,51-66H/t45-,46-,51-,52-,53-,54-,55+,56+/m1/s1

Standard InChI Key:  YQQUILZPDYJDQJ-KGDQSQJYSA-N

Alternative Forms

1. Parent:

   

   ALA384120

   Hopeaphenol

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: 906.94

Molecular Weight (Monoisotopic): 906.2676

AlogP: 10.43

#Rotatable Bonds: 5

Polar Surface Area: 220.76

Molecular Species: NEUTRAL

HBA: 12

HBD: 10

#RO5 Violations: 4

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 8.69

CX Basic pKa:

CX LogP: 10.43

CX LogD: 10.41

Aromatic Rings: 8

Heavy Atoms: 68

QED Weighted: 0.08

Np Likeness Score: 0.80

References

1. Ohyama M, Tanaka T, Ito T, Iinuma M, Bastow KF, Lee KH..  (1999)  Antitumor agents 200. Cytotoxicity of naturally occurring resveratrol oligomers and their acetate derivatives.,  9  (20): [PMID:10571175] [10.1016/s0960-894x(99)00520-x]

2. Abe N, Ito T, Ohguchi K, Nasu M, Masuda Y, Oyama M, Nozawa Y, Ito M, Iinuma M..  (2010)  Resveratrol oligomers from Vatica albiramis.,  73  (9): [PMID:20735051] [10.1021/np1002675]

3. Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Kon'i H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O..  (2012)  Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii.,  20  (2): [PMID:22209731] [10.1016/j.bmc.2011.11.067]

4. Davis RA, Beattie KD, Xu M, Yang X, Yin S, Holla H, Healy PC, Sykes M, Shelper T, Avery VM, Elofsson M, Sundin C, Quinn RJ..  (2014)  Solving the supply of resveratrol tetramers from Papua New Guinean rainforest anisoptera species that inhibit bacterial type III secretion systems.,  77  (12): [PMID:25405587] [10.1021/np500433z]

5. Lyons BJE, Strynadka NCJ..  (2019)  On the road to structure-based development of anti-virulence therapeutics targeting the type III secretion system injectisome.,  10  (8): [PMID:31534650] [10.1039/C9MD00146H]

6. Mattio LM, Catinella G, Pinto A, Dallavalle S..  (2020)  Natural and nature-inspired stilbenoids as antiviral agents.,  202  [PMID:32652408] [10.1016/j.ejmech.2020.112541]

7. Williams DE, Cassel J, Zhu JL, Yang JX, de Voogd NJ, Matainaho T, Salvino JM, Wang YA, Montaner LJ, Tietjen I, Andersen RJ..  (2023)  Thorectidiol A Isolated from the Marine Sponge Dactylospongia elegans Disrupts Interactions of the SARS-CoV-2 Spike Receptor Binding Domain with the Host ACE2 Receptor.,  86  (3): [PMID:36657039] [10.1021/acs.jnatprod.2c01030]

Source

Source(1):

• Scientific Literature