(R)-4-guanidinobutyl 1-imino-3-nonyl-1,2,3,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-4-carboxylate

ID: ALA3577350

PubChem CID: 122177648

Max Phase: Preclinical

Molecular Formula: C22H40N6O2

Molecular Weight: 420.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCC[C@H]1NC(=N)N2CCCC2=C1C(=O)OCCCCNC(=N)N

Standard InChI:  InChI=1S/C22H40N6O2/c1-2-3-4-5-6-7-8-12-17-19(18-13-11-15-28(18)22(25)27-17)20(29)30-16-10-9-14-26-21(23)24/h17H,2-16H2,1H3,(H2,25,27)(H4,23,24,26)/t17-/m1/s1

Standard InChI Key:  CNYOJFKISRGTCX-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -2.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971    3.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    3.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935    3.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    5.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    6.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5785    7.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749    8.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691    9.7848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1655   10.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0336   10.0445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1610   11.7409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267    2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300    3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380    5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2413    5.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2494    7.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5527    8.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5607    9.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6028   10.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  4  2  1  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
  4  9  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 11 12  2  0
 11 13  1  0
  6 11  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  7 22  1  6
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577350

   ---

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: 420.60

Molecular Weight (Monoisotopic): 420.3213

AlogP: 3.19

#Rotatable Bonds: 14

Polar Surface Area: 127.32

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 12.00

CX LogP: 3.14

CX LogD: -1.54

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.13

Np Likeness Score: 0.09

References

1. Jamison MT, Molinski TF..  (2015)  Antipodal crambescin A2 homologues from the marine sponge Pseudaxinella reticulata. Antifungal structure-activity relationships.,  78  (3): [PMID:25738226] [10.1021/np501052a]

Source

Source(1):

• Scientific Literature