(1S*,2R*,3R*,5R*,7a*R)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine

ID: ALA509589

PubChem CID: 11127013

Max Phase: Preclinical

Molecular Formula: C9H17NO3

Molecular Weight: 187.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Hyacinthacine A6 | Hyacinthacine A6|CHEMBL509589|SCHEMBL2437360

Canonical SMILES:  C[C@@H]1CC[C@@H]2[C@H](O)[C@H](O)[C@@H](CO)N12

Standard InChI:  InChI=1S/C9H17NO3/c1-5-2-3-6-8(12)9(13)7(4-11)10(5)6/h5-9,11-13H,2-4H2,1H3/t5-,6-,7-,8+,9-/m1/s1

Standard InChI Key:  AGLLYYHKZWZSKX-GOFVFXDOSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   17.9884  -11.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4855  -11.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0101  -10.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2079  -11.5236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2195  -10.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4413  -10.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9488  -11.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4227  -11.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2125   -9.8750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2760   -9.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3104  -11.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2299  -12.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1568  -12.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6675  -13.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  4  5  1  0
  5  9  1  1
  4  1  1  0
  3 10  1  6
  2 11  1  6
  1  2  1  0
  1 12  1  1
  2  3  1  0
  8 13  1  6
  3  5  1  0
 12 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA509589

   HYACINTHACINE A6

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: 187.24

Molecular Weight (Monoisotopic): 187.1208

AlogP: -1.06

#Rotatable Bonds: 1

Polar Surface Area: 63.93

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.21

CX Basic pKa: 9.61

CX LogP: -0.99

CX LogD: -3.18

Aromatic Rings: ┄

Heavy Atoms: 13

QED Weighted: 0.49

Np Likeness Score: 1.91

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