O-2-Amino-2,3,4-trideoxy-alpha-D-glycero-hex-4-enopyranosyl(1->4)garamine

ID: ALA3245224

Chembl Id: CHEMBL3245224

PubChem CID: 71297177

Max Phase: Preclinical

Molecular Formula: C19H36N4O8

Molecular Weight: 448.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3OC(CO)=CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

Standard InChI:  InChI=1S/C19H36N4O8/c1-19(27)7-28-18(13(26)16(19)23-2)31-15-11(22)5-10(21)14(12(15)25)30-17-9(20)4-3-8(6-24)29-17/h3,9-18,23-27H,4-7,20-22H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1

Standard InChI Key:  IZDCJSIPHXBXBL-YFMIWBNJSA-N

Alternative Forms

1. Parent:

   

   ALA3245224

   (1s,2s,3r,4s,6r)-4,6-Diamino-3-{[(2s,3r)-3-Amino-6-(Hydroxymethyl)-3,4-Dihydro-2h-Pyran-2-Yl]oxy}-2-Hydroxycyclohexyl 3-Deoxy-4-C-Methyl-3-(Methylamino)-Beta-L-Arabinopyranoside

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: 448.52

Molecular Weight (Monoisotopic): 448.2533

AlogP: -3.82

#Rotatable Bonds: 6

Polar Surface Area: 207.93

Molecular Species: BASE

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.54

CX Basic pKa: 9.68

CX LogP: -4.21

CX LogD: -9.90

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.20

Np Likeness Score: 1.88

References

1. Davies DH, Mallams AK, Counelis M, Loebenberg D, Moss EL, Waitz JA..  (1978)  Semisynthetic aminoglycoside antibacterials. 6. Synthesis of sisomicin, Antibiotic G-52, and novel 6'-substituted analogues of sisomicin from aminoglycoside 66-40C.,  21  (2): [PMID:413921] [10.1021/jm00200a009]

Source

Source(1):

• Scientific Literature