4-(((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(carbamoyloxy)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-19-yl)amino)methyl)cyclohexanecarboxylicacid

ID: ALA4794663

PubChem CID: 162673049

Max Phase: Preclinical

Molecular Formula: C36H51N3O10

Molecular Weight: 685.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@H]1/C=C\C=C(/C)C(=O)NC2=CC(=O)C(NCC3CCC(C(=O)O)CC3)=C(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@@H]1OC(N)=O)C2=O

Standard InChI:  InChI=1S/C36H51N3O10/c1-19-14-25-30(38-18-23-10-12-24(13-11-23)35(44)45)27(40)17-26(32(25)42)39-34(43)20(2)8-7-9-28(47-5)33(49-36(37)46)22(4)16-21(3)31(41)29(15-19)48-6/h7-9,16-17,19,21,23-24,28-29,31,33,38,41H,10-15,18H2,1-6H3,(H2,37,46)(H,39,43)(H,44,45)/b9-7-,20-8+,22-16+/t19-,21+,23?,24?,28+,29+,31-,33+/m1/s1

Standard InChI Key:  LGYRVCYOCBKGHK-ULLGIGRLSA-N

Molfile:  

 
     RDKit          2D

 49 51  0  0  0  0  0  0  0  0999 V2000
   22.9584   -6.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2417   -6.5643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6279   -7.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9652   -7.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7874   -7.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2557   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9702   -4.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2557   -3.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9702   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6846   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6846   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6846   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6833   -4.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6833   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3978   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3978   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1123   -6.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8267   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1123   -7.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6833   -6.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9689   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8251   -5.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5413   -4.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3978   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1123   -4.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8228   -4.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8251   -3.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1106   -2.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3939   -3.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1123   -5.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1114   -2.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3403   -8.3982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0864   -9.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6392   -9.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2796   -9.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5537   -8.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9689   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2406   -5.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6788   -2.8657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9650   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2499   -2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2509   -2.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5399   -1.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8236   -2.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8228   -2.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5383   -3.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1102   -1.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1121   -0.7977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3947   -2.0335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  3  4  2  0
  4  5  1  0
  5  1  1  0
 23  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
  7 12  1  0
 11  1  1  0
 24 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  3  1  0
 18 22  1  1
 17 19  1  1
 16 20  1  1
 20 21  1  0
 26 23  1  0
 24 25  1  0
 24 29  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 25 30  2  0
 28 31  2  0
  5 32  1  1
 32 33  1  0
 33 34  1  0
 33 35  2  0
  4 36  1  0
 14 37  1  6
  2 38  1  0
 29 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 41 46  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 44 47  1  0
 47 48  2  0
 47 49  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794663

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 685.81

Molecular Weight (Monoisotopic): 685.3574

AlogP: 3.24

#Rotatable Bonds: 7

Polar Surface Area: 203.58

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.26

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 0.18

Aromatic Rings: ┄

Heavy Atoms: 49

QED Weighted: 0.19

Np Likeness Score: 2.02

References

1. Skrzypczak N,Pyta K,Ruszkowski P,Gdaniec M,Bartl F,Przybylski P.  (2020)  Synthesis, structure and anticancer activity of new geldanamycin amine analogs containing C(17)- or C(20)- flexible and rigid arms as well as closed or open ansa-bridges.,  202  [PMID:32663707] [10.1016/j.ejmech.2020.112624]

Source

Source(1):

• Scientific Literature