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

ID: ALA505166

PubChem CID: 11116780

Max Phase: Preclinical

Molecular Formula: C9H17NO3

Molecular Weight: 187.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Hyacinthacine A7 | Hyacinthacine A7|CHEMBL505166

Canonical SMILES:  C[C@H]1CC[C@@H]2[C@H](O)[C@H](O)[C@@H](CO)N21

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+/m0/s1

Standard InChI Key:  AGLLYYHKZWZSKX-JTPBWFLFSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   -2.6826  -16.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856  -15.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6610  -14.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631  -16.0205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4516  -15.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2298  -14.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7223  -15.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2484  -16.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4585  -14.3718    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951  -14.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606  -15.6435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411  -17.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5143  -17.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035  -17.6805    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  1
  3  5  1  0
 12 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA505166

   HYACINTHACINE A7

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