ID: ALA49623

Max Phase: Preclinical

Molecular Formula: C21H27NO2

Molecular Weight: 325.45

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@H]([C@H](O)c1ccc(O)cc1)N1CCC(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3/t16-,21-/m0/s1

Standard InChI Key:  UYNVMODNBIQBMV-KKSFZXQISA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 325.45

Molecular Weight (Monoisotopic): 325.2042

AlogP: 3.77

#Rotatable Bonds: 5

Polar Surface Area: 43.70

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.67

CX Basic pKa: 9.03

CX LogP: 3.57

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.88

Np Likeness Score: 0.06

References

1. Büttelmann B, Alanine A, Bourson A, Gill R, Heitz MP, Mutel V, Pinard E, Trube G, Wyler R..  (2003)  4-(3,4-dihydro-1H-isoquinolin-2yl)-pyridines and 4-(3,4-dihydro-1H-isoquinolin-2-yl)-quinolines as potent NR1/2B subtype selective NMDA receptor antagonists.,  13  (10): [PMID:12729659] [10.1016/s0960-894x(03)00232-4]

2. Zhou ZL, Cai SX, Whittemore ER, Konkoy CS, Espitia SA, Tran M, Rock DM, Coughenour LL, Hawkinson JE, Boxer PA, Bigge CF, Wise LD, Weber E, Woodward RM, Keana JF..  (1999)  4-Hydroxy-1-[2-(4-hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine: a novel, potent, and selective NR1/2B NMDA receptor antagonist.,  42  (15): [PMID:10425109] [10.1021/jm990246i]

3. Chenard BL, Shalaby IA, Koe BK, Ronau RT, Butler TW, Prochniak MA, Schmidt AW, Fox CB..  (1991)  Separation of alpha 1 adrenergic and N-methyl-D-aspartate antagonist activity in a series of ifenprodil compounds.,  34  (10): [PMID:1681106] [10.1021/jm00114a018]

4. Chenard BL, Shalaby IA, Koe BK, Ronau RT, Butler TW, Prochniak MA, Schmidt AW, Fox CB..  (1991)  Separation of alpha 1 adrenergic and N-methyl-D-aspartate antagonist activity in a series of ifenprodil compounds.,  34  (10): [PMID:1681106] [10.1021/jm00114a018]

5. Chenard BL, Bordner J, Butler TW, Chambers LK, Collins MA, De Costa DL, Ducat MF, Dumont ML, Fox CB, Mena EE..  (1995)  (1S,2S)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol: a potent new neuroprotectant which blocks N-methyl-D-aspartate responses.,  38  (16): [PMID:7636876] [10.1021/jm00016a017]

6. Claiborne CF, McCauley JA, Libby BE, Curtis NR, Diggle HJ, Kulagowski JJ, Michelson SR, Anderson KD, Claremon DA, Freidinger RM, Bednar RA, Mosser SD, Gaul SL, Connolly TM, Condra CL, Bednar B, Stump GL, Lynch JJ, Macaulay A, Wafford KA, Koblan KS, Liverton NJ..  (2003)  Orally efficacious NR2B-selective NMDA receptor antagonists.,  13  (4): [PMID:12639561] [10.1016/s0960-894x(02)01061-2]

7. Büttelmann B, Alanine A, Bourson A, Gill R, Heitz MP, Mutel V, Pinard E, Trube G, Wyler R..  (2003)  2-(3,4-Dihydro-1H-isoquinolin-2yl)-pyridines as a novel class of NR1/2B subtype selective NMDA receptor antagonists.,  13  (5): [PMID:12617901] [10.1016/s0960-894x(03)00007-6]

8. Chenard B, Butler T, Shalaby I, Prochniak M, Koe B, Fox C.  (1993)  Oxindole N-Methyl-D-Aspartate (NMDA) antagonists,  3  (1): [10.1016/S0960-894X(00)80098-0]

9. PubChem BioAssay data set, 

10. Thum S, Schepmann D, Ayet E, Pujol M, Nieto FR, Ametamey SM, Wünsch B..  (2019)  Tetrahydro-3-benzazepines with fluorinated side chains as NMDA and σ₁ receptor antagonists: Synthesis, receptor affinity, selectivity and antiallodynic activity.,  177  [PMID:31129453] [10.1016/j.ejmech.2019.05.034]

11. Bechthold E,Schreiber JA,Lehmkuhl K,Frehland B,Schepmann D,Bernal FA,Daniliuc C,Álvarez I,Garcia CV,Schmidt TJ,Seebohm G,Wünsch B.  (2021)  Ifenprodil Stereoisomers: Synthesis, Absolute Configuration, and Correlation with Biological Activity.,  64  (2.0): [PMID:33426889] [10.1021/acs.jmedchem.0c01912]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays