Erythro-5,6-bis(4-hydroxyphenyl)-N-(2-chloroethyl)-1-octylamine Hydrochloride

ID: ALA2368609

PubChem CID: 73355985

Max Phase: Preclinical

Molecular Formula: C23H33Cl2NO2

Molecular Weight: 389.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@](C)(c1ccc(O)cc1)[C@H](CCCCNCCCl)c1ccc(O)cc1.Cl

Standard InChI:  InChI=1S/C23H32ClNO2.ClH/c1-3-23(2,19-9-13-21(27)14-10-19)22(6-4-5-16-25-17-15-24)18-7-11-20(26)12-8-18;/h7-14,22,25-27H,3-6,15-17H2,1-2H3;1H/t22-,23-;/m1./s1

Standard InChI Key:  JYFOVTRIHSIJTI-OHIDFYLOSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
    6.0226    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9254    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6399    0.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -0.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6399    1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3544    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035   -1.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -2.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0689    1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -2.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0689    0.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035   -2.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3544    2.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614    0.4675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379   -0.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5048    0.0550    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7833    2.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -3.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7903    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629   -0.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5035   -0.3575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  2  0
  4  7  1  0
  5  8  2  0
  5  9  1  0
  8 12  1  0
 10 12  2  0
  7 13  2  0
 11 13  1  0
  9 14  2  0
 10 14  1  0
  6 15  1  0
 11 15  2  0
  2 17  1  0
  2 18  1  6
 11 20  1  0
 10 21  1  0
  3 22  1  0
 16 23  1  0
 16 24  1  0
 19 25  1  0
 23 25  1  0
 22 26  1  0
 17 27  1  0
 24 28  1  0
 26 28  1  0
  3 29  1  6
M  END

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: 389.97

Molecular Weight (Monoisotopic): 389.2122

AlogP: 5.55

#Rotatable Bonds: 11

Polar Surface Area: 52.49

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.99

CX Basic pKa: 9.30

CX LogP: 5.60

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.35

Np Likeness Score: 0.06

References

1. Köhle H, Krohn K, Leclercq G..  (1989)  Hexestrol-linked cytotoxic agents: synthesis and binding affinity for estrogen receptors.,  32  (7): [PMID:2544725] [10.1021/jm00127a023]

Source

Source(1):

• Scientific Literature