2,10-Dihydroxy-6-({[2-(hydroxymethyl)pyridin-4-yl]methyl}amino)-13-(beta-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione

ID: ALA507006

PubChem CID: 44565966

Max Phase: Preclinical

Molecular Formula: C33H29N5O11

Molecular Weight: 671.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2c(c3c4ccc(O)cc4n(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3c3[nH]c4cc(O)ccc4c23)C(=O)N1NCc1ccnc(CO)c1

Standard InChI:  InChI=1S/C33H29N5O11/c39-11-14-7-13(5-6-34-14)10-35-37-31(46)24-22-17-3-1-15(41)8-19(17)36-26(22)27-23(25(24)32(37)47)18-4-2-16(42)9-20(18)38(27)49-33-30(45)29(44)28(43)21(12-40)48-33/h1-9,21,28-30,33,35-36,39-45H,10-12H2/t21-,28-,29+,30-,33+/m1/s1

Standard InChI Key:  WSTZEXQZDPGROF-OJSVXGLKSA-N

Molfile:  

     RDKit          2D

 49 56  0  0  0  0  0  0  0  0999 V2000
   18.4315  -10.9044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6141  -11.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4738  -11.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2016  -12.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7960  -11.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6874  -14.2899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5108  -14.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0084  -15.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8274  -14.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1509  -14.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6554  -13.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8308  -13.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2104  -13.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7626  -12.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7802  -13.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5005  -13.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6074  -11.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0397  -10.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8108  -10.1782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0397  -13.3850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9668  -12.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5893  -11.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7649  -11.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3145  -11.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6921  -12.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5165  -12.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3264  -15.5837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4881  -11.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0190  -14.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2975  -14.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5926  -14.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8733  -14.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8516  -15.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5556  -15.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2813  -15.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1706  -14.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5355  -16.6392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1911  -13.3114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1285  -15.7811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9849  -15.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3692   -9.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7504   -8.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5704   -8.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9514   -7.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5099   -7.2961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6830   -7.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3056   -8.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2391   -6.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6176   -5.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 20 15  1  0
 14 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 20 26  1  0
 21 26  2  0
 10 11  2  0
  9 27  1  0
 11 12  1  0
 24 28  1  0
  7 12  2  0
 12 13  1  0
 30 29  1  1
 30 31  1  0
 13  4  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 13 16  2  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
  6 16  1  0
 32 36  1  1
 34 37  1  1
  5 17  2  0
 36 38  1  0
  1  2  1  0
 33 39  1  6
  2 18  2  0
 35 40  1  6
 29 20  1  0
  2  3  1  0
 19 41  1  0
  1 19  1  0
 41 42  1  0
  3  4  2  0
 42 43  2  0
  4  5  1  0
 43 44  1  0
  1  5  1  0
 44 45  2  0
  6  7  1  0
 45 46  1  0
  7  8  1  0
 46 47  2  0
 47 42  1  0
  8  9  2  0
 46 48  1  0
  9 10  1  0
 48 49  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA507006

   6,20-dihydroxy-13-[[2-(hydroxymethyl)pyridin-4-yl]methylamino]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione

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: 671.62

Molecular Weight (Monoisotopic): 671.1864

AlogP: 0.26

#Rotatable Bonds: 7

Polar Surface Area: 243.09

Molecular Species: NEUTRAL

HBA: 14

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.75

CX Basic pKa: 3.05

CX LogP: -0.64

CX LogD: -0.66

Aromatic Rings: 6

Heavy Atoms: 49

QED Weighted: 0.10

Np Likeness Score: 0.65

References

1. Sunami S, Nishimura T, Nishimura I, Ito S, Arakawa H, Ohkubo M..  (2009)  Synthesis and biological activities of topoisomerase I inhibitors, 6-arylmethylamino analogues of edotecarin.,  52  (10): [PMID:19397324] [10.1021/jm801641t]

Source

Source(1):

• Scientific Literature