4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenol

ID: ALA397836

Chembl Id: CHEMBL397836

Cas Number: 69829-90-9

PubChem CID: 739395

Max Phase: Preclinical

Molecular Formula: C8H6N2O2S

Molecular Weight: 194.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(-c2n[nH]c(=S)o2)cc1

Standard InChI:  InChI=1S/C8H6N2O2S/c11-6-3-1-5(2-4-6)7-9-10-8(13)12-7/h1-4,11H,(H,10,13)

Standard InChI Key:  NGBOFOYNPCHKQQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA397836

   4-(5-Mercapto-1,3,4-oxadiazol-2-yl)phenol

Molecule Features

Natural Product: No

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: 194.22

Molecular Weight (Monoisotopic): 194.0150

AlogP: 2.10

#Rotatable Bonds: 1

Polar Surface Area: 62.05

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.46

CX Basic pKa: ┄

CX LogP: 2.25

CX LogD: 1.56

Aromatic Rings: 2

Heavy Atoms: 13

QED Weighted: 0.68

Np Likeness Score: -0.50

References

1. Gupta S, Chhibber M, Sinha S, Surolia A..  (2007)  Design of mechanism-based inhibitors of transthyretin amyloidosis: studies with biphenyl ethers and new structural templates.,  50  (23): [PMID:17948976] [10.1021/jm0700159]

2. Khan KM, Fatima N, Rasheed M, Jalil S, Ambreen N, Perveen S, Choudhary MI..  (2009)  1,3,4-Oxadiazole-2(3H)-thione and its analogues: a new class of non-competitive nucleotide pyrophosphatases/phosphodiesterases 1 inhibitors.,  17  (22): [PMID:19822431] [10.1016/j.bmc.2009.09.011]

3. Ghani U, Ullah N..  (2010)  New potent inhibitors of tyrosinase: novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site.,  18  (11): [PMID:20452224] [10.1016/j.bmc.2010.04.021]

4. Bera H, Chigurupati S..  (2016)  Recent discovery of non-nucleobase thymidine phosphorylase inhibitors targeting cancer.,  124  [PMID:27783978] [10.1016/j.ejmech.2016.10.032]

5. Taha M, Rashid U, Imran S, Ali M..  (2018)  Rational design of bis-indolylmethane-oxadiazole hybrids as inhibitors of thymidine phosphorylase.,  26  (12): [PMID:29853339] [10.1016/j.bmc.2018.05.046]

6. Verma SK,Verma R,Verma S,Vaishnav Y,Tiwari SP,Rakesh KP.  (2021)  Anti-tuberculosis activity and its structure-activity relationship (SAR) studies of oxadiazole derivatives: A key review.,  209  [PMID:33032083] [10.1016/j.ejmech.2020.112886]

7. Sharma A, De Rosa M, Singla N, Singh G, Barnwal RP, Pandey A..  (2021)  Tuberculosis: An Overview of the Immunogenic Response, Disease Progression, and Medicinal Chemistry Efforts in the Last Decade toward the Development of Potential Drugs for Extensively Drug-Resistant Tuberculosis Strains.,  64  (8.0): [PMID:33826327] [10.1021/acs.jmedchem.0c01833]

8. Zhang HZ, Zhao ZL, Zhou CH..  (2018)  Recent advance in oxazole-based medicinal chemistry.,  144  [PMID:29288945] [10.1016/j.ejmech.2017.12.044]

Source

Source(1):

• Scientific Literature