PIBROZELESIN HYDROBROMIDE

ID: ALA2106438

Cas Number: 148778-32-9

PubChem CID: 10078959

Max Phase: Unknown

Molecular Formula: C32H37Br2N5O8

Molecular Weight: 698.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pibrozelesin hbr | Pibrozelesin hydrobromide | KW-2189 | Pibrozelesin hydrobromide|KW-2189|Pibrozelesin hbr|148778-32-9|Pibrozelesin hydrobromide [USAN]|0481JCC90T|Pibrozelesin hydrobromide (USAN)|methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate;hydrobromide|Methyl (S)-8-(bromomethyl)-3,6,7,8-tetrahydro-4-hydroxy-2-methyl-6-((5,6,7-trimethoxyindol-2-yl)carbonyl)benzo(1,2-b:4,3-b')Show More⌵

Canonical SMILES:  Br.COC(=O)c1c(C)[nH]c2c(OC(=O)N3CCN(C)CC3)cc3c(c12)[C@H](CBr)CN3C(=O)c1cc2cc(OC)c(OC)c(OC)c2[nH]1

Standard InChI:  InChI=1S/C32H36BrN5O8.BrH/c1-16-23(31(40)45-6)25-24-18(14-33)15-38(20(24)13-21(27(25)34-16)46-32(41)37-9-7-36(2)8-10-37)30(39)19-11-17-12-22(42-3)28(43-4)29(44-5)26(17)35-19;/h11-13,18,34-35H,7-10,14-15H2,1-6H3;1H/t18-;/m1./s1

Standard InChI Key:  YMALQNICPSISCA-GMUIIQOCSA-N

Molfile:  

     RDKit          2D

 47 51  0  0  0  0  0  0  0  0999 V2000
    3.1417   -5.1875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -1.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -2.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -1.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -4.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -3.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -5.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -3.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750   -0.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -2.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5750   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -1.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -0.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -0.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    0.4958    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -6.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  8  2  0
  5  2  1  0
  6 12  1  0
  7 14  2  0
  8  5  1  0
  9  7  1  0
 10  3  2  0
 11  6  1  0
 12  2  1  0
 13 11  1  0
 14 19  1  0
 15 13  1  0
 16 24  1  0
 17 21  1  0
 18 20  1  0
 19  5  2  0
 20  2  1  0
 21  6  2  0
 22 15  2  0
 23 16  1  0
 24 14  1  0
 25  3  1  0
 26 27  2  0
 27 17  1  0
 28 36  1  0
 29 12  2  0
 30 16  2  0
 31 23  1  0
 32 23  1  0
 33 25  2  0
 34 15  1  0
 35 31  1  0
 36 32  1  0
 37 22  1  0
 18 38  1  6
 39 25  1  0
 40 26  1  0
 41 10  1  0
 42 38  1  0
 43 28  1  0
 44 34  1  0
 45 37  1  0
 46 39  1  0
 47 40  1  0
  8 18  1  0
 17 13  2  0
  7  4  1  0
  9 10  1  0
 26 22  1  0
 28 35  1  0
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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 698.57

Molecular Weight (Monoisotopic): 697.1747

AlogP: 4.66

#Rotatable Bonds: 7

Polar Surface Area: 138.66

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.85

CX Basic pKa: 6.82

CX LogP: 2.89

CX LogD: 2.79

Aromatic Rings: 4

Heavy Atoms: 46

QED Weighted: 0.21

Np Likeness Score: -0.43

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Wolfe AL, Duncan KK, Parelkar NK, Weir SJ, Vielhauer GA, Boger DL..  (2012)  A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct.,  55  (12): [PMID:22650244] [10.1021/jm300330b]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names