6'-N-(2-Phenylethyl)sisomicin

ID: ALA3245222

PubChem CID: 90672129

Max Phase: Preclinical

Molecular Formula: C27H45N5O7

Molecular Weight: 551.68

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(CNCCc4ccccc4)=CC[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

Standard InChI:  InChI=1S/C27H45N5O7/c1-27(35)14-36-26(21(34)24(27)31-2)39-23-19(30)12-18(29)22(20(23)33)38-25-17(28)9-8-16(37-25)13-32-11-10-15-6-4-3-5-7-15/h3-8,17-26,31-35H,9-14,28-30H2,1-2H3/t17-,18+,19-,20+,21-,22-,23+,24-,25-,26-,27+/m1/s1

Standard InChI Key:  KAXRXPAMDOAIAY-DBTGHZAVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3245222

   (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-[(2-phenylethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

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: 551.68

Molecular Weight (Monoisotopic): 551.3319

AlogP: -1.98

#Rotatable Bonds: 10

Polar Surface Area: 199.73

Molecular Species: BASE

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.55

CX Basic pKa: 9.73

CX LogP: -1.87

CX LogD: -8.95

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.15

Np Likeness Score: 1.28

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