5,6,8,5',6',8'-Hexahydroxy-2,3,2',3'-tetramethyl-2,3,2',3'-tetrahydro-[9,9']bi[benzo[g]chromenyl]-4,4'-dione

ID: ALA162783

Chembl Id: CHEMBL162783

Cas Number: 75514-37-3

PubChem CID: 53277

Max Phase: Preclinical

Molecular Formula: C30H26O10

Molecular Weight: 546.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1Oc2cc3c(-c4c(O)cc(O)c5c(O)c6c(cc45)OC(C)C(C)C6=O)c(O)cc(O)c3c(O)c2C(=O)C1C

Standard InChI:  InChI=1S/C30H26O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-12,31-34,37-38H,1-4H3

Standard InChI Key:  RHNVLFNWDGWACV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA162783

   Chaetochromin

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: 546.53

Molecular Weight (Monoisotopic): 546.1526

AlogP: 5.09

#Rotatable Bonds: 1

Polar Surface Area: 173.98

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.48

CX Basic pKa: ┄

CX LogP: 5.67

CX LogD: 5.37

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.19

Np Likeness Score: 1.21

References

1. Singh SB, Zink DL, Bills GF, Teran A, Silverman KC, Lingham RB, Felock P, Hazuda DJ..  (2003)  Four novel bis-(naphtho-gamma-pyrones) isolated from Fusarium species as inhibitors of HIV-1 integrase.,  13  (4): [PMID:12639565] [10.1016/s0960-894x(02)01057-0]

2. Singh SB, Zink DL, Bills GF, Teran A, Silverman KC, Lingham RB, Felock P, Hazuda DJ..  (2003)  Four novel bis-(naphtho-gamma-pyrones) isolated from Fusarium species as inhibitors of HIV-1 integrase.,  13  (4): [PMID:12639565] [10.1016/s0960-894x(02)01057-0]

3. Rogers JP, Beuscher AE, Flajolet M, McAvoy T, Nairn AC, Olson AJ, Greengard P..  (2006)  Discovery of protein phosphatase 2C inhibitors by virtual screening.,  49  (5): [PMID:16509582] [10.1021/jm051033y]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. Tomek P, Palmer BD, Flanagan JU, Sun C, Raven EL, Ching LM..  (2017)  Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.,  126  [PMID:28011425] [10.1016/j.ejmech.2016.12.029]

8. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Natural Product Set III,  [10.6019/CHEMBL4296183]

9.  (2018)  Yap1 inhibitors that target the interaction of yap1 with oct4, 

10. Capochiani de Iudicibus R, Tomek P, Palmer BD, Tijono SM, Flanagan JU, Ching LM..  (2021)  Parallel discovery of selective and dual inhibitors of tryptophan dioxygenases IDO1 and TDO2 with a newly-modified enzymatic assay.,  39  [PMID:33901770] [10.1016/j.bmc.2021.116160]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data