Adociaquinone B

ID: ALA476648

Chembl Id: CHEMBL476648

Max Phase: Preclinical

Molecular Formula: C22H17NO6S

Molecular Weight: 423.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12CCCc3coc(c31)C(=O)c1cc3c(cc12)C(=O)C1=C(NCCS1(=O)=O)C3=O

Standard InChI:  InChI=1S/C22H17NO6S/c1-22-4-2-3-10-9-29-20(15(10)22)18(25)13-7-11-12(8-14(13)22)19(26)21-16(17(11)24)23-5-6-30(21,27)28/h7-9,23H,2-6H2,1H3/t22-/m0/s1

Standard InChI Key:  KJMXEMKLXNMFIG-QFIPXVFZSA-N

Alternative Forms

1. Parent:

   

   ALA476648

   ADOCIAQUINONE B

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: 423.45

Molecular Weight (Monoisotopic): 423.0777

AlogP: 2.07

#Rotatable Bonds: ┄

Polar Surface Area: 110.52

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.10

CX LogD: 1.10

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: 1.76

References

1. Concepción GP, Foderaro TA, Eldredge GS, Lobkovsky E, Clardy J, Barrows LR, Ireland CM..  (1995)  Topoisomerase II-mediated DNA cleavage by adocia- and xestoquinones from the Philippine sponge Xestospongia sp.,  38  (22): [PMID:7473578] [10.1021/jm00022a016]

2. Braud E, Goddard ML, Kolb S, Brun MP, Mondésert O, Quaranta M, Gresh N, Ducommun B, Garbay C..  (2008)  Novel naphthoquinone and quinolinedione inhibitors of CDC25 phosphatase activity with antiproliferative properties.,  16  (19): [PMID:18789703] [10.1016/j.bmc.2008.08.009]

3. Cao S, Murphy BT, Foster C, Lazo JS, Kingston DG..  (2009)  Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases.,  17  (6): [PMID:19028102] [10.1016/j.bmc.2008.10.090]

4. Lavecchia A, Di Giovanni C, Pesapane A, Montuori N, Ragno P, Martucci NM, Masullo M, De Vendittis E, Novellino E..  (2012)  Discovery of new inhibitors of Cdc25B dual specificity phosphatases by structure-based virtual screening.,  55  (9): [PMID:22524450] [10.1021/jm201624h]

5. Du L, Mahdi F, Datta S, Jekabsons MB, Zhou YD, Nagle DG..  (2012)  Structures and mechanisms of antitumor agents: xestoquinones uncouple cellular respiration and disrupt HIF signaling in human breast tumor cells.,  75  (9): [PMID:22938093] [10.1021/np3002892]

Source

Source(1):

• Scientific Literature