(Z)-(2-(Hydroxymethyl)-4-((1-methyl-5-nitro-1H-indol-3-yl)-methylene)-5-oxotetrahydrofuran-2-yl)methyl Pivalate

ID: ALA4164472

PubChem CID: 145959564

Max Phase: Preclinical

Molecular Formula: C21H24N2O7

Molecular Weight: 416.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(/C=C2/CC(CO)(COC(=O)C(C)(C)C)OC2=O)c2cc([N+](=O)[O-])ccc21

Standard InChI:  InChI=1S/C21H24N2O7/c1-20(2,3)19(26)29-12-21(11-24)9-13(18(25)30-21)7-14-10-22(4)17-6-5-15(23(27)28)8-16(14)17/h5-8,10,24H,9,11-12H2,1-4H3/b13-7-

Standard InChI Key:  LWIQJWIQVPZBME-QPEQYQDCSA-N

Molfile:  

     RDKit          2D

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    3.4710  -22.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1850  -22.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4757  -21.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387  -22.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601  -22.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5144  -22.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8515  -21.6327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961  -21.8675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646  -23.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663  -23.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615  -22.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520  -21.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379  -22.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0567  -20.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317  -21.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3347  -22.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273  -22.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4817  -23.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424  -23.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9666  -22.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7378  -24.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9584  -24.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7823  -25.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3846  -25.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1657  -25.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3382  -24.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2094  -26.4174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062  -22.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8135  -26.9731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4310  -26.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  2  4  1  0
  6  8  2  0
  5  9  2  0
  1 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 13 16  1  0
 13 17  1  0
  9 18  1  0
 18 22  1  0
 21 19  1  0
 19 20  1  0
 20 18  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 19 28  1  0
 27 29  2  0
 27 30  1  0
M  CHG  2  27   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4164472

   ---

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: 416.43

Molecular Weight (Monoisotopic): 416.1584

AlogP: 2.74

#Rotatable Bonds: 5

Polar Surface Area: 120.90

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -0.09

References

1. Ann J, Czikora A, Saini AS, Zhou X, Mitchell GA, Lewin NE, Peach ML, Blumberg PM, Lee J..  (2018)  α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands.,  61  (14): [PMID:29860841] [10.1021/acs.jmedchem.8b00661]

Source

Source(1):

• Scientific Literature