Momusine B

ID: ALA2409550

PubChem CID: 71814505

Max Phase: Preclinical

Molecular Formula: C20H19BrN6O6S

Molecular Weight: 551.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[S+]([O-])C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](OC(=O)c2c[nH]c3cc(Br)c(O)cc23)[C@@H]1O

Standard InChI:  InChI=1S/C20H19BrN6O6S/c1-34(31)5-13-15(29)16(19(32-13)27-7-26-14-17(22)24-6-25-18(14)27)33-20(30)9-4-23-11-3-10(21)12(28)2-8(9)11/h2-4,6-7,13,15-16,19,23,28-29H,5H2,1H3,(H2,22,24,25)/t13-,15-,16-,19-,34?/m1/s1

Standard InChI Key:  FILFITGGBFZWAD-XODDSCPXSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    9.7518   -8.6604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.4396   -6.9002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0915   -7.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2457   -6.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3383   -5.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5767   -5.5712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5086   -8.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0169   -6.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2826   -7.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9550   -8.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1961   -8.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0924   -5.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9104   -7.2119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7571   -6.0579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6707   -6.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3450   -8.4688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1788   -4.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1300   -9.8154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4756   -9.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0358   -9.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7493   -7.8291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6798   -9.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5061   -9.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1881   -9.9001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9164  -10.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7302   -9.8780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0629   -8.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8175   -9.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4870   -8.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4034   -7.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6442   -7.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9778   -7.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5569   -6.5796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0767   -7.2564    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1
  4  2  1  0
  5  4  2  0
  6  8  2  0
  7  3  1  0
  8  2  1  0
  9  3  1  0
 10  7  1  0
 11  9  1  0
 12  5  1  0
 13  4  1  0
 14 15  1  0
 15 13  2  0
  7 16  1  6
 17 12  1  0
 10 18  1  6
 11 19  1  1
  5  6  1  0
 10 11  1  0
 14 12  2  0
 19  1  1  0
  1 20  1  0
  1 21  1  0
 16 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  2  0
 25 26  1  0
 26 28  1  0
 27 23  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 31 33  1  0
 30 34  1  0
M  CHG  2   1   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2409550

   [(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(methylsulfinylmethyl)oxolan-3-yl] 6-bromo-5-hydroxy-1H-indole-3-carboxylate

Molecule Features

Natural Product: Yes

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: 551.38

Molecular Weight (Monoisotopic): 550.0270

AlogP: 1.22

#Rotatable Bonds: 5

Polar Surface Area: 184.46

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.63

CX Basic pKa: 3.94

CX LogP: 0.23

CX LogD: 0.03

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: 0.79

References

1. Li JL, Kim EL, Wang H, Hong J, Shin S, Lee CK, Jung JH..  (2013)  Epimeric methylsulfinyladenosine derivatives from the marine ascidian Herdmania momus.,  23  (16): [PMID:23810281] [10.1016/j.bmcl.2013.05.097]

2. Li JL, Kim EL, Wang H, Hong J, Shin S, Lee CK, Jung JH..  (2013)  Epimeric methylsulfinyladenosine derivatives from the marine ascidian Herdmania momus.,  23  (16): [PMID:23810281] [10.1016/j.bmcl.2013.05.097]

Source

Source(1):

• Scientific Literature