8N-[2-amino-(1S)-cyclohexyl]-15-oxo-(9aR,13aR)-10,11,12,13,15,15a-hexahydro-4aH-benzo[7,8]quinazolino[5,4-ab]phenazine-8-carboxamide

ID: ALA3707108

PubChem CID: 44294468

Max Phase: Preclinical

Molecular Formula: C21H24N4O6

Molecular Weight: 428.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@]12C(COC(N)=O)C3=C(C(=O)C(C)=C(NCCc4ccco4)C3=O)N1CC1NC12

Standard InChI:  InChI=1S/C21H24N4O6/c1-10-15(23-6-5-11-4-3-7-30-11)18(27)14-12(9-31-20(22)28)21(29-2)19-13(24-19)8-25(21)16(14)17(10)26/h3-4,7,12-13,19,23-24H,5-6,8-9H2,1-2H3,(H2,22,28)/t12?,13?,19?,21-/m1/s1

Standard InChI Key:  DHELVIXTUBOIOD-BQHYEGLBSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  1  0  0  0  0  0999 V2000
    1.5008   -3.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -4.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120   -4.6560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2104   -3.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217   -4.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0062   -3.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074   -4.6389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -5.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059   -3.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059   -4.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2052   -4.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2052   -3.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066   -5.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507   -2.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -1.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0420   -3.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059   -2.3422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059   -5.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363   -4.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523   -2.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -3.1609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988   -3.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453   -0.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526   -3.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526   -4.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4575   -4.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040   -1.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -4.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370   -3.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264   -3.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -3.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  1  0
  5  3  1  0
  6  1  1  0
  7  2  1  0
  8  2  1  0
  9  4  1  0
 10  5  1  0
 11 10  1  0
 12  9  1  0
 13  3  1  0
 14  6  1  0
 15 20  1  0
 16 29  1  0
 17  9  2  0
 18 10  2  0
 19 16  1  0
 20 14  1  0
 21 12  1  0
  1 22  1  6
 23 15  2  0
 24 16  2  0
 25 19  1  0
 26 24  1  0
 27 15  1  0
 28 11  1  0
 29 30  1  0
 30 21  1  0
 31 22  1  0
  8 13  1  0
  5  4  2  0
  8  7  1  0
 11 12  2  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3707108

   [(7R)-11-[2-(furan-2-yl)ethylamino]-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

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: 428.45

Molecular Weight (Monoisotopic): 428.1696

AlogP: -0.18

#Rotatable Bonds: 7

Polar Surface Area: 146.04

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.60

CX LogP: 0.23

CX LogD: 0.22

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: 1.04

References

1. Gilligan PJ, Robertson DW, Zaczek R..  (2000)  Corticotropin releasing factor (CRF) receptor modulators: progress and opportunities for new therapeutic agents.,  43  (9): [PMID:10794681] [10.1021/jm990590f]

2. Iyengar BS, Sami SM, Takahashi T, Sikorski EE, Remers WA, Bradner WT..  (1986)  Mitomycin C analogues with increased metal complexing ability.,  29  (9): [PMID:3091833] [10.1021/jm00159a033]

3. Kunz KR, Iyengar BS, Dorr RT, Alberts DS, Remers WA..  (1991)  Structure-activity relationships for mitomycin C and mitomycin A analogues.,  34  (7): [PMID:1906109] [10.1021/jm00111a051]

Source

Source(1):

• Scientific Literature