ID: ALA1640
Max Phase: Approved
First Approval: 2004
Molecular Formula: C34H24N6Na4O14S4
Molecular Weight: 872.89
Molecule Type: Small molecule
Associated Items:
Synonyms (12): Benzamine blue | Benzo blue | C.i. 23850 | C.i. direct blue 14 | Congo blue | Diamine blue | Dianil blue | Naphthylamine blue | Niagara blue | Trypan blue | Visionblue | NSC-11247
Synonyms from Alternative Forms(12):
Canonical SMILES: Cc1cc(-c2ccc(/N=N/c3c(S(=O)(=O)[O-])cc4cc(S(=O)(=O)[O-])cc(N)c4c3O)c(C)c2)ccc1/N=N/c1c(S(=O)(=O)[O-])cc2cc(S(=O)(=O)[O-])cc(N)c2c1O.[Na+].[Na+].[Na+].[Na+]
Standard InChI: InChI=1S/C34H28N6O14S4.4Na/c1-15-7-17(3-5-25(15)37-39-31-27(57(49,50)51)11-19-9-21(55(43,44)45)13-23(35)29(19)33(31)41)18-4-6-26(16(2)8-18)38-40-32-28(58(52,53)54)12-20-10-22(56(46,47)48)14-24(36)30(20)34(32)42;;;;/h3-14,41-42H,35-36H2,1-2H3,(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54);;;;/q;4*+1/p-4/b39-37+,40-38+;;;;
Standard InChI Key: GLNADSQYFUSGOU-GPTZEZBUSA-J
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: Yes | First In Class: No | Black Box: No |
| Chirality: Yes | Availability: Yes | Prodrug: No |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
| Molecular Weight: 872.89 | Molecular Weight (Monoisotopic): 872.0546 | AlogP: 6.67 | #Rotatable Bonds: 9 |
| Polar Surface Area: 359.42 | Molecular Species: ACID | HBA: 16 | HBD: 8 |
| #RO5 Violations: 4 | HBA (Lipinski): 20 | HBD (Lipinski): 10 | #RO5 Violations (Lipinski): 4 |
| CX Acidic pKa: -3.90 | CX Basic pKa: 2.38 | CX LogP: 1.13 | CX LogD: -3.61 |
| Aromatic Rings: 6 | Heavy Atoms: 58 | QED Weighted: 0.04 | Np Likeness Score: -0.25 |
| 1. Jacobson KA, Jarvis MF, Williams M.. (2002) Purine and pyrimidine (P2) receptors as drug targets., 45 (19): [PMID:12213051] [10.1021/jm020046y] |
| 2. Shrestha S, Shim YS, Kim KC, Lee KH, Cho H.. (2004) Evans Blue and other dyes as protein tyrosine phosphatase inhibitors., 14 (8): [PMID:15050628] [10.1016/j.bmcl.2004.01.079] |
| 3. Liao YH, Houghton PJ, Hoult JR.. (1999) Novel and known constituents from Buddleja species and their activity against leukocyte eicosanoid generation., 62 (9): [PMID:10514305] [10.1021/np990092+] |
| 4. Etoga JL, Ahmed SK, Patel S, Bridges RJ, Thompson CM.. (2010) Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system x(c)(-) over the vesicular glutamate transporter., 20 (8): [PMID:20303751] [10.1016/j.bmcl.2009.10.020] |
| 5. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A.. (2010) Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species., 23 (1): [PMID:20014752] [10.1021/tx900326k] |
| 6. Unpublished dataset, |
| 7. Carrigan CN, Patel SA, Cox HD, Bolstad ES, Gerdes JM, Smith WE, Bridges RJ, Thompson CM.. (2014) The development of benzo- and naphtho-fused quinoline-2,4-dicarboxylic acids as vesicular glutamate transporter (VGLUT) inhibitors reveals a possible role for neuroactive steroids., 24 (3): [PMID:24424130] [10.1016/j.bmcl.2013.12.086] |
| 8. Favre-Besse FC, Poirel O, Bersot T, Kim-Grellier E, Daumas S, El Mestikawy S, Acher FC, Pietrancosta N.. (2014) Design, synthesis and biological evaluation of small-azo-dyes as potent Vesicular Glutamate Transporters inhibitors., 78 [PMID:24686010] [10.1016/j.ejmech.2014.03.056] |
| 9. WHO Anatomical Therapeutic Chemical Classification, |
Source(3):
