ID: ALA7075

Max Phase: Phase

Molecular Formula: C20H23N3O2S2

Molecular Weight: 401.56

Molecule Type: Small molecule

Representations

Synonyms (6): Sheta-2 | Sheta2 | NSC-721689 | NSC-726189 | SHETA-2 | SHETA2
Synonyms from Alternative Forms(6):

Canonical SMILES:  CC1(C)CC(C)(C)c2cc(NC(=S)Nc3ccc([N+](=O)[O-])cc3)ccc2S1

Standard InChI:  InChI=1S/C20H23N3O2S2/c1-19(2)12-20(3,4)27-17-10-7-14(11-16(17)19)22-18(26)21-13-5-8-15(9-6-13)23(24)25/h5-11H,12H2,1-4H3,(H2,21,22,26)

Standard InChI Key:  FWWKIYPMUZVMQG-UHFFFAOYSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 401.56

Molecular Weight (Monoisotopic): 401.1232

AlogP: 5.96

#Rotatable Bonds: 3

Polar Surface Area: 67.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.63

CX Basic pKa:

CX LogP: 6.03

CX LogD: 6.03

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: -1.19

References

1. Liu S, Brown CW, Berlin KD, Dhar A, Guruswamy S, Brown D, Gardner GJ, Birrer MJ, Benbrook DM..  (2004)  Synthesis of flexible sulfur-containing heteroarotinoids that induce apoptosis and reactive oxygen species with discrimination between malignant and benign cells.,  47  (4): [PMID:14761202] [10.1021/jm030346v]

2. Liu S, Louie MC, Rajagopalan V, Zhou G, Ponce E, Nguyen T, Green L..  (2015)  Synthesis and evaluation of the diarylthiourea analogs as novel anti-cancer agents.,  25  (6): [PMID:25701251] [10.1016/j.bmcl.2015.01.042]

3. Gnanasekaran KK, Benbrook DM, Nammalwar B, Thavathiru E, Bunce RA, Berlin KD..  (2015)  Synthesis and evaluation of second generation Flex-Het scaffolds against the human ovarian cancer A2780 cell line.,  96  [PMID:25880346] [10.1016/j.ejmech.2015.03.070]

4. Watts FM, Pouland T, Bunce RA, Berlin KD, Benbrook DM, Mashayekhi M, Bhandari D, Zhou D..  (2018)  Activity of oxygen-versus sulfur-containing analogs of the Flex-Het anticancer agent SHetA2.,  158  [PMID:30245396] [10.1016/j.ejmech.2018.09.036]

5. Nammalwar B, Bunce RA, Berlin KD, Benbrook DM, Toal C..  (2019)  Synthesis and biological evaluation of SHetA2 (NSC-721689) analogs against the ovarian cancer cell line A2780.,  170  [PMID:30878829] [10.1016/j.ejmech.2019.03.010]

6. Gnanasekaran KK, Pouland T, Bunce RA, Darrell Berlin K, Abuskhuna S, Bhandari D, Mashayekhi M, Zhou DH, Benbrook DM..  (2020)  Tetrahydroquinoline units in flexible heteroarotinoids (Flex-Hets) convey anti-cancer properties in A2780 ovarian cancer cells.,  28  (1): [PMID:31831296] [10.1016/j.bmc.2019.115244]

7. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates