(2S,3S,4S,5S,6R)-2-((2R,3S,4S,5R,6R)-3,5-dihydroxy-2-((2R,3R,4R,5R)-4-hydroxy-2-(2-hydroxyethyl)-5-(hydroxymethyl)pyrrolidin-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA522570

PubChem CID: 10391299

Max Phase: Preclinical

Molecular Formula: C19H35NO14

Molecular Weight: 501.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC[C@H]1N[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O

Standard InChI:  InChI=1S/C19H35NO14/c21-2-1-6-16(10(25)7(3-22)20-6)33-19-15(30)17(12(27)9(5-24)32-19)34-18-14(29)13(28)11(26)8(4-23)31-18/h6-30H,1-5H2/t6-,7-,8-,9-,10-,11-,12-,13+,14+,15+,16-,17+,18+,19+/m1/s1

Standard InChI Key:  VQRBHGFKZAPWHE-LTHFBJLESA-N

Molfile:  

     RDKit          2D

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    7.7417   -2.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8916   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2693   -2.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2250   -7.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -7.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9374   -8.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5126   -6.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  1  1  0
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 30 32  1  0
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 32 34  1  1
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 15 16  1  0
 25 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA522570

   (2S,3S,4S,5S,6R)-2-((2R,3S,4S,5R,6R)-3,5-dihydroxy-2-((2R,3R,4R,5R)-4-hydroxy-2-(2-hydroxyethyl)-5-(hydroxymethyl)pyrrolidin-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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: 501.48

Molecular Weight (Monoisotopic): 501.2058

AlogP: -6.93

#Rotatable Bonds: 9

Polar Surface Area: 251.25

Molecular Species: BASE

HBA: 15

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.93

CX Basic pKa: 9.06

CX LogP: -6.37

CX LogD: -8.03

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: 1.70

References

1. Yamashita T, Yasuda K, Kizu H, Kameda Y, Watson AA, Nash RJ, Fleet GW, Asano N..  (2002)  New polyhydroxylated pyrrolidine, piperidine, and pyrrolizidine alkaloids from Scilla sibirica.,  65  (12): [PMID:12502331] [10.1021/np020296h]

Source

Source(1):

• Scientific Literature