4-[[(4,4-dimethyl-3,4-dihydro-2H-benzo[b]pyran-6-yl)-carbonyl]oxy]benzaldehyde thiosemicarbazone

ID: ALA119880

PubChem CID: 44345706

Max Phase: Preclinical

Molecular Formula: C20H21N3O3S

Molecular Weight: 383.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCOc2ccc(C(=O)Oc3ccc(/C=N\N=C(/N)S)cc3)cc21

Standard InChI:  InChI=1S/C20H21N3O3S/c1-20(2)9-10-25-17-8-5-14(11-16(17)20)18(24)26-15-6-3-13(4-7-15)12-22-23-19(21)27/h3-8,11-12H,9-10H2,1-2H3,(H3,21,23,27)/b22-12-

Standard InChI Key:  SMLQDCCTDXVYIJ-UUYOSTAYSA-N

Molfile:  

     RDKit          2D

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    4.4292   -8.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -8.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -8.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292   -8.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667   -8.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -8.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2875   -9.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7125   -7.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4375   -9.2292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7167   -7.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -9.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -7.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -9.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -9.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1417   -7.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -6.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -8.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -9.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -8.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -8.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -6.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -8.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -7.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -7.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  3  2  0
  5 11  2  0
  6  1  1  0
  7  2  1  0
  8  1  2  0
  9 17  2  0
 10  5  1  0
 11  9  1  0
 12  8  1  0
 13  2  2  0
 14 15  2  0
 15  8  1  0
 16  5  1  0
 17 19  1  0
 18  7  1  0
 19 23  1  0
 20 12  1  0
 21 18  2  0
 22 18  1  0
 23 22  2  0
 24 21  1  0
 25  6  1  0
 26  6  1  0
 27  6  1  0
 25 20  1  0
  4 14  1  0
 24 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA119880

   [4-[(Z)-(carbamothioylhydrazinylidene)methyl]phenyl] 4,4-dimethyl-2,3-dihydrochromene-6-carboxylate

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: 383.47

Molecular Weight (Monoisotopic): 383.1304

AlogP: 3.54

#Rotatable Bonds: 4

Polar Surface Area: 86.27

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.66

CX Basic pKa: 3.67

CX LogP: 4.34

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.21

Np Likeness Score: -0.42

References

1. Benbrook DM, Madler MM, Spruce LW, Birckbichler PJ, Nelson EC, Subramanian S, Weerasekare GM, Gale JB, Patterson MK, Wang B, Wang W, Lu S, Rowland TC, DiSivestro P, Lindamood C, Hill DL, Berlin KD..  (1997)  Biologically active heteroarotinoids exhibiting anticancer activity and decreased toxicity.,  40  (22): [PMID:9357524] [10.1021/jm970196m]

Source

Source(1):

• Scientific Literature