2-adamantanamine

ID: ALA1170792

Cas Number: 13074-39-0

PubChem CID: 25332

Product Number: A586946, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H17N

Molecular Weight: 151.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Adamantanamine | 2-aminoadamantane|adamantan-2-amine|13074-39-0|2-Adamantanamine|2-Adamantylamine|Tricyclo[3.3.1.13,7]decan-2-amine|JP 60|adamantan-2-ylamine|CHEMBL1170792|MFCD00078225|Tricyclo(3.3.1.1(3,7))decan-2-amine|Tricyclo(3.3.1.13,7)decan-2-amine|2-amino-adamantane|NSC 127842|Oprea1_605085|SCHEMBL75970|AC17|SCHEMBL2400612|SCHEMBL4657616|SCHEMBL4688717|SCHEMBL7436572|SCHEMBL12876277|SCHEMBL13243472|SCHEMBL15088151|SCHEMBL17203865|DTXSID90156707|HMS1787I03|BDBM50482329|NSC127842|AKOS0001Show More⌵

Synonyms from Alternative Forms(1): Adamantan-2-Ylamine HCl

Canonical SMILES:  NC1C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C10H17N/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-10H,1-5,11H2

Standard InChI Key:  QZWNXXINFABALM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 13  0  0  0  0  0  0  0  0999 V2000
   -4.1041   -9.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -8.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938   -9.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7415   -9.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5355   -9.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882   -9.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2965   -8.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358   -7.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4627   -8.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -8.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2906   -7.7828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 10 11  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1170792

   2-Adamantylamine hydrochloride

2. Parent:

   

   ALA1170792

   Adamantan-2-amine

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: 151.25

Molecular Weight (Monoisotopic): 151.1361

AlogP: 1.77

#Rotatable Bonds: ┄

Polar Surface Area: 26.02

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.54

CX LogP: 1.55

CX LogD: -1.23

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.56

Np Likeness Score: 0.23

References

1. Eleftheratos S, Spearpoint P, Ortore G, Kolocouris A, Martinelli A, Martin S, Hay A..  (2010)  Interaction of aminoadamantane derivatives with the influenza A virus M2 channel-docking using a pore blocking model.,  20  (14): [PMID:20570509] [10.1016/j.bmcl.2010.05.049]

2. Kolocouris A, Tzitzoglaki C, Johnson FB, Zell R, Wright AK, Cross TA, Tietjen I, Fedida D, Busath DD..  (2014)  Aminoadamantanes with persistent in vitro efficacy against H1N1 (2009) influenza A.,  57  (11): [PMID:24793875] [10.1021/jm500598u]

3. Tzitzoglaki C, Wright A, Freudenberger K, Hoffmann A, Tietjen I, Stylianakis I, Kolarov F, Fedida D, Schmidtke M, Gauglitz G, Cross TA, Kolocouris A..  (2017)  Binding and Proton Blockage by Amantadine Variants of the Influenza M2WT and M2S31N Explained.,  60  (5): [PMID:28107633] [10.1021/acs.jmedchem.6b01115]

4. Wu S, Wang Y, Liu N, Dong G, Sheng C..  (2017)  Tackling Fungal Resistance by Biofilm Inhibitors.,  60  (6): [PMID:28051303] [10.1021/acs.jmedchem.6b01203]

Source

Source(1):

• Scientific Literature