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

ID: ALA452641

PubChem CID: 11041480

Max Phase: Preclinical

Molecular Formula: C9H17NO3

Molecular Weight: 187.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Hyacinthacine A5 | Hyacinthacine A5|CHEMBL452641

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-OKNNCHMLSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   13.6801  -11.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1772  -11.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7017  -10.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8996  -11.7152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9111  -10.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1330  -10.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6405  -11.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1144  -11.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9042  -10.0667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9676   -9.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0020  -11.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9216  -12.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8485  -12.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3592  -13.3750    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  1
  2 11  1  1
  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:

   

   ALA452641

   HYACINTHACINE A5

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