3-[(3-p-Tolyl-adamantane-1-carbonyl)-amino]-benzoic acid

ID: ALA597965

Cas Number: 413593-49-4

PubChem CID: 2834598

Max Phase: Preclinical

Molecular Formula: C25H27NO3

Molecular Weight: 389.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZINC 01467812 | CHEMBL597965|ZINC 01467812|413593-49-4|3-[3-(4-methylphenyl)adamantane-1-amido]benzoic acid|3-({[3-(4-methylphenyl)-1-adamantyl]carbonyl}amino)benzoic acid|CBMicro_048173|Oprea1_240053|BDBM50481419|AKOS001039712|AKOS016879745|BIM-0048031.P001|EN300-26867107|SR-01000399451|SR-01000399451-1|Z56864069

Canonical SMILES:  Cc1ccc(C23CC4CC(CC(C(=O)Nc5cccc(C(=O)O)c5)(C4)C2)C3)cc1

Standard InChI:  InChI=1S/C25H27NO3/c1-16-5-7-20(8-6-16)24-11-17-9-18(12-24)14-25(13-17,15-24)23(29)26-21-4-2-3-19(10-21)22(27)28/h2-8,10,17-18H,9,11-15H2,1H3,(H,26,29)(H,27,28)

Standard InChI Key:  YMTISLCQXGXNOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    4.6906   -5.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881   -5.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0696   -5.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0833   -6.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5018   -6.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672   -5.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -6.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8809   -6.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7701   -6.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5055   -6.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2195   -5.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2411   -6.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -6.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2195   -4.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -4.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5055   -5.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6906   -4.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0767   -9.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -9.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -9.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -8.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -8.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -8.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -9.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623  -10.6570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -9.4196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -7.3570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5055   -6.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200   -7.3569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
 12  1  1  0
 13  1  1  0
 14 15  1  0
 10 12  1  0
  9 11  1  0
  9 10  1  0
 17 15  1  0
 15 16  1  0
  1  2  1  0
  2  3  2  0
  4  5  1  0
  2  7  1  0
  3  6  1  0
  6  4  2  0
  5  7  2  0
  4  8  1  0
  1 17  1  0
 10 16  1  0
 11 14  1  0
 18 24  1  0
 20 21  2  0
 24 25  2  0
 24 26  1  0
 21 22  1  0
 22 27  1  0
 19 20  1  0
 27 28  1  0
 22 23  2  0
 28 10  1  0
 23 18  1  0
 28 29  2  0
 18 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA597965

   3-({[3-(4-Methylphenyl)-1-adamantyl]carbonyl}amino)benzoic acid

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: 389.50

Molecular Weight (Monoisotopic): 389.1991

AlogP: 5.17

#Rotatable Bonds: 4

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.92

CX Basic pKa: ┄

CX LogP: 5.42

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.76

Np Likeness Score: -0.85

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature