protoapigenone

ID: ALA414890

Chembl Id: CHEMBL414890

Cas Number: 862884-32-0

PubChem CID: 11644907

Max Phase: Preclinical

Molecular Formula: C15H10O6

Molecular Weight: 286.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Protoapigenone | Protoapigenone|MLS000574831|SMR000156275|862884-32-0|5,7-Dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)-4H-chromen-4-one|5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)chromen-4-one|CHEMBL414890|SCHEMBL13066080|BDBM43766|cid_11644907|REGID_for_CID_11644907|HY-134008|CS-0136497|5,7-dihydroxy-2-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)chromone|5,7-bis(oxidanyl)-2-(1-oxidanyl-4-oxidanylidene-cyclohexa-2,5-dien-1-yl)chromen-4-one|5,7-dihydroxy-2-(1-hydroxy-4-oxo-1-cyShow More⌵

Canonical SMILES:  O=C1C=CC(O)(c2cc(=O)c3c(O)cc(O)cc3o2)C=C1

Standard InChI:  InChI=1S/C15H10O6/c16-8-1-3-15(20,4-2-8)13-7-11(19)14-10(18)5-9(17)6-12(14)21-13/h1-7,17-18,20H

Standard InChI Key:  DLMOVPAUHQQYHA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA414890

   PROTOAPIGENONE

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: 286.24

Molecular Weight (Monoisotopic): 286.0477

AlogP: 1.09

#Rotatable Bonds: 1

Polar Surface Area: 107.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.58

CX Basic pKa: ┄

CX LogP: 1.72

CX LogD: 0.80

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: 2.16

References

1. Lin AS, Nakagawa-Goto K, Chang FR, Yu D, Morris-Natschke SL, Wu CC, Chen SL, Wu YC, Lee KH..  (2007)  First total synthesis of protoapigenone and its analogues as potent cytotoxic agents.,  50  (16): [PMID:17622129] [10.1021/jm070363a]

2. Chang FR, Hayashi K, Chua NH, Kamio S, Huang ZY, Nozaki H, Wu YC..  (2005)  The transgenic Arabidopsis plant system, pER8-GFP, as a powerful tool in searching for natural product estrogen-agonists/antagonists.,  68  (7): [PMID:16038533] [10.1021/np050121i]

3. PubChem BioAssay data set, 

4. Yuan Q, Liu Z, Xiong C, Wu L, Wang J, Ruan J..  (2011)  A novel, broad-spectrum antitumor compound containing the 1-hydroxycyclohexa-2,5-dien-4-one group: the disclosure of a new antitumor pharmacophore in protoapigenone 1.,  21  (11): [PMID:21515048] [10.1016/j.bmcl.2011.03.108]

5. Xie Y, Dahlin JL, Oakley AJ, Casarotto MG, Board PG, Baell JB..  (2018)  Reviewing Hit Discovery Literature for Difficult Targets: Glutathione Transferase Omega-1 as an Example.,  61  (17): [PMID:29652143] [10.1021/acs.jmedchem.8b00318]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays