4-Fluoro-17-(2-iodo-vinyl)-11-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA1628166

PubChem CID: 53318446

Max Phase: Preclinical

Molecular Formula: C21H26FIO3

Molecular Weight: 472.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1C[C@@]2(C)[C@@H](CC[C@@]2(O)/C=C/I)[C@@H]2CCc3c(ccc(O)c3F)[C@H]21

Standard InChI:  InChI=1S/C21H26FIO3/c1-20-11-17(26-2)18-12-5-6-16(24)19(22)13(12)3-4-14(18)15(20)7-8-21(20,25)9-10-23/h5-6,9-10,14-15,17-18,24-25H,3-4,7-8,11H2,1-2H3/b10-9+/t14-,15-,17-,18+,20-,21+/m0/s1

Standard InChI Key:  HSQUNGACABVJBQ-RQMIOOJKSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    9.7617   -5.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6330   -6.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0195   -6.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388   -5.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7373   -5.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6086   -7.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3714   -5.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0808   -4.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4673   -4.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9029   -7.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0031   -7.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2895   -7.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9519   -5.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1237   -6.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1730   -4.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2218   -7.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1481   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2463   -6.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9758   -4.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8784   -8.3009    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6903   -4.6976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4917   -3.9916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7821   -4.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3985   -3.7453    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -7.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9768   -5.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -6.7167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -5.4792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7917   -6.7208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  7  1  0
  5  1  1  0
  6  2  2  0
  7  8  1  0
  8  1  1  0
  9  1  1  0
 10  6  1  0
 11  3  1  0
 12 11  1  0
 13  2  1  0
 14  5  1  0
  9 15  1  0
 16 18  1  0
 17  9  1  0
 18 13  2  0
 19 15  2  0
 20 10  1  0
  7 21  1  1
  9 22  1  1
  1 23  1  1
 24 19  1  0
 25 16  1  0
 26 21  1  0
 17 14  1  0
  4  3  1  0
 12  6  1  0
 16 10  2  0
  4 27  1  6
  3 28  1  1
  5 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1628166

   (8S,9S,11S,13S,14S,17R)-4-fluoro-17-[(E)-2-iodoethenyl]-11-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

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: 472.34

Molecular Weight (Monoisotopic): 472.0911

AlogP: 4.69

#Rotatable Bonds: 2

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.42

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: 1.48

References

1. Ali H, Rousseau J, van Lier JE..  (1993)  Synthesis of A-ring fluorinated derivatives of (17 alpha,20E/Z)-[125I]iodovinylestradiols: effect on receptor binding and receptor-mediated target tissue uptake.,  36  (21): [PMID:8230092] [10.1021/jm00073a004]

2. Ali H, Rousseau J, van Lier JE..  (1993)  Synthesis of A-ring fluorinated derivatives of (17 alpha,20E/Z)-[125I]iodovinylestradiols: effect on receptor binding and receptor-mediated target tissue uptake.,  36  (21): [PMID:8230092] [10.1021/jm00073a004]

3. Gantchev TG, Ali H, van Lier JE..  (1994)  Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives.,  37  (24): [PMID:7990116] [10.1021/jm00050a013]

Source

Source(1):

• Scientific Literature