(1R*,2R*,3R*,5R*,7S*,7a*R)-3-hydroxymethyl-5-methyl-1,2,7-trihydroxypyrrolizidine

ID: ALA523761

PubChem CID: 10976560

Max Phase: Preclinical

Molecular Formula: C9H17NO4

Molecular Weight: 203.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Hyacinthacine B4 | Hyacinthacine B4|CHEMBL523761|BDBM50278884|(1R,2R,3R,5R,7S,8R)-3-(hydroxymethyl)-5-methyl-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2,7-triol|(1R*,2R*,3R*,5R*,7S*,7a*R)-3-hydroxymethyl-5-methyl-1,2,7-trihydroxypyrrolizidine

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

Standard InChI:  InChI=1S/C9H17NO4/c1-4-2-6(12)7-9(14)8(13)5(3-11)10(4)7/h4-9,11-14H,2-3H2,1H3/t4-,5-,6+,7-,8-,9-/m1/s1

Standard InChI Key:  PIBHCJDPQRCONN-FJYMVOSHSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    8.5265  -16.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0236  -15.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5482  -15.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7460  -16.3456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7576  -15.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793  -15.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4868  -15.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9607  -16.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7506  -14.6969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8141  -14.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486  -15.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7680  -17.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6948  -17.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2056  -18.0055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7354  -14.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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  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
  5  6  1  0
  6 15  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA523761

   HYACINTHACINE B4

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: 203.24

Molecular Weight (Monoisotopic): 203.1158

AlogP: -2.09

#Rotatable Bonds: 1

Polar Surface Area: 84.16

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.15

CX Basic pKa: 9.01

CX LogP: -2.14

CX LogD: -3.76

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.39

Np Likeness Score: 2.41

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]

2. Carroll AW, Willis AC, Hoshino M, Kato A, Pyne SG..  (2019)  Corrected Structure of Natural Hyacinthacine C1 via Total Synthesis.,  82  (2): [PMID:30714734] [10.1021/acs.jnatprod.8b00879]

Source

Source(1):

• Scientific Literature