Androsta-3,5,16-triene-17-benzimidazol-1-yl

ID: ALA4520316

PubChem CID: 66850189

Max Phase: Preclinical

Molecular Formula: C26H30N2

Molecular Weight: 370.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CCC=CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(n3cnc4ccccc43)=CC[C@@H]12

Standard InChI:  InChI=1S/C26H30N2/c1-25-15-6-5-7-18(25)10-11-19-20-12-13-24(26(20,2)16-14-21(19)25)28-17-27-22-8-3-4-9-23(22)28/h3-5,7-10,13,17,19-21H,6,11-12,14-16H2,1-2H3/t19-,20-,21-,25-,26-/m0/s1

Standard InChI Key:  SPEDTVSELPTCNP-HKGZJRCASA-N

Molfile:  

 
     RDKit          2D

 31 36  0  0  0  0  0  0  0  0999 V2000
    7.4113  -10.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8414  -10.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4060  -11.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6275  -10.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6904  -11.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6943  -12.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6978  -11.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0984  -11.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989  -13.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8197  -12.2629    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6057  -11.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859  -11.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779  -12.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8280  -11.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779  -11.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1072  -11.0212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859  -13.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1152  -11.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1117  -12.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8944   -9.6035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1322  -10.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3988  -12.2462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8363   -9.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6741   -9.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6873   -8.5399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4189   -8.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9122   -8.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5928   -7.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7844   -7.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2965   -8.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6145   -8.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 19  1  0
  6  9  2  0
 21  1  1  0
  2 14  1  0
  3 22  1  6
  4  2  1  0
  7  5  1  1
 14 10  1  6
  7 12  1  0
 11  8  1  0
 18 16  1  1
  2 21  1  0
  3  1  1  0
  2 23  1  1
  3 18  1  0
 14 11  1  0
 15 13  1  0
 17  6  1  0
  7  6  1  0
 15 12  1  0
 19 18  1  0
 13 17  2  0
 18 14  1  0
  4 20  1  0
  7  3  1  0
  8  4  2  0
 20 24  1  0
 24 25  2  0
 25 27  1  0
 26 20  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520316

   1-[(8R,9S,10R,13S,14S)-10,13-dimethyl-2,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthren-17-yl]benzimidazole

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 370.54

Molecular Weight (Monoisotopic): 370.2409

AlogP: 6.62

#Rotatable Bonds: 1

Polar Surface Area: 17.82

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.97

CX LogP: 5.49

CX LogD: 5.49

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: 1.32

References

1. Purushottamachar P, Kwegyir-Afful AK, Martin MS, Ramamurthy VP, Ramalingam S, Njar VC..  (2016)  Identification of Novel Steroidal Androgen Receptor Degrading Agents Inspired by Galeterone 3β-Imidazole Carbamate.,  7  (7): [PMID:27437082] [10.1021/acsmedchemlett.6b00137]

Source

Source(1):

• Scientific Literature