(5S,6S,7S,7aR)-5-Hydroxymethyl-3-[(9-phenylnonyl)imino]tetrahydro-pyrrolo[1,2-c]-thiazole-6,7-diol

ID: ALA3907041

PubChem CID: 134135085

Max Phase: Preclinical

Molecular Formula: C22H34N2O3S

Molecular Weight: 406.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1[C@H](O)[C@@H](O)[C@@H]2CS/C(=N/CCCCCCCCCc3ccccc3)N12

Standard InChI:  InChI=1S/C22H34N2O3S/c25-15-18-20(26)21(27)19-16-28-22(24(18)19)23-14-10-5-3-1-2-4-7-11-17-12-8-6-9-13-17/h6,8-9,12-13,18-21,25-27H,1-5,7,10-11,14-16H2/b23-22+/t18-,19-,20-,21-/m0/s1

Standard InChI Key:  FGWIOFZYMGZOKY-QQHMXMNYSA-N

Molfile:  

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   18.5674   -8.4129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1375  -13.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4194  -14.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7958  -15.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6242  -15.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0680  -14.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3907041

   ---

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: 406.59

Molecular Weight (Monoisotopic): 406.2290

AlogP: 2.83

#Rotatable Bonds: 11

Polar Surface Area: 76.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 6.32

CX LogP: 3.87

CX LogD: 3.83

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: 0.39

References

1. Miyawaki S, Hirokami Y, Kinami K, Hoshino M, Minehira D, Miyamoto D, Nash RJ, Fleet GW, Adachi I, Toyooka N, Kato A..  (2017)  Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.,  25  (1): [PMID:27789075] [10.1016/j.bmc.2016.10.015]

Source

Source(1):

• Scientific Literature