4-[(4,4-Dimethyl-chroman-6-carbonyl)-methoxy-amino]-benzoic acid methyl ester

ID: ALA138844

PubChem CID: 11793457

Max Phase: Preclinical

Molecular Formula: C21H23NO5

Molecular Weight: 369.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(N(OC)C(=O)c2ccc3c(c2)C(C)(C)CCO3)cc1

Standard InChI:  InChI=1S/C21H23NO5/c1-21(2)11-12-27-18-10-7-15(13-17(18)21)19(23)22(26-4)16-8-5-14(6-9-16)20(24)25-3/h5-10,13H,11-12H2,1-4H3

Standard InChI Key:  ANHGSIRAKDNVNC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.9125   -3.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8375   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875   -2.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -4.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5042   -2.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9125   -3.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -1.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  1  0
  5  3  2  0
  6 10  1  0
  7  4  1  0
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  9  2  1  0
 10 18  1  0
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 19 16  1  0
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 27 21  1  0
  8  4  2  0
 10 19  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA138844

   Methyl 4-[(4,4-dimethyl-2,3-dihydrochromene-6-carbonyl)-methoxyamino]benzoate

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: 369.42

Molecular Weight (Monoisotopic): 369.1576

AlogP: 3.74

#Rotatable Bonds: 4

Polar Surface Area: 65.07

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.17

References

1. Zacheis D, Dhar A, Lu S, Madler MM, Klucik J, Brown CW, Liu S, Clement F, Subramanian S, Weerasekare GM, Berlin KD, Gold MA, Houck JR, Fountain KR, Benbrook DM..  (1999)  Heteroarotinoids inhibit head and neck cancer cell lines in vitro and in vivo through both RAR and RXR retinoic acid receptors.,  42  (21): [PMID:10543887] [10.1021/jm990292i]

Source

Source(1):

• Scientific Literature