Hyrtioreticulin

The hyrtioreticulins are a series of indole alkaloids, named hyrtioreticulin A through hyrtioreticulin F, that were isolated from Hyrtios reticulatus, an ocean sponge.[1][2]

Hyrtioreticulin
Names
IUPAC name
    • A: (1R,3S)-6-hydroxy-1-(1H-imidazol-5-ylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
    • B: (1S,3S)-6-hydroxy-1-(1H-imidazol-5-ylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
    • C: (9R,11S)-7-hydroxy-9-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4(13),5,7-tetraene-11-carboxylic acid
    • D: (9S,11S)-7-hydroxy-9-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4(13),5,7-tetraene-11-carboxylic acid
    • E: (1R,3S)-6-hydroxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
    • F: (1S,3S)-5-[(1R)-1-(carboxymethylamino)ethyl]-6-hydroxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • A: InChI=1S/C16H16N4O3/c21-9-1-2-12-10(4-9)11-5-14(16(22)23)19-13(15(11)20-12)3-8-6-17-7-18-8/h1-2,4,6-7,13-14,19-21H,3,5H2,(H,17,18)(H,22,23)/t13-,14+/m1/s1
    Key: VXURZHPEJYLPGK-KGLIPLIRSA-N
  • B: InChI=1S/C16H16N4O3/c21-9-1-2-12-10(4-9)11-5-14(16(22)23)19-13(15(11)20-12)3-8-6-17-7-18-8/h1-2,4,6-7,13-14,19-21H,3,5H2,(H,17,18)(H,22,23)/t13-,14-/m0/s1
    Key: VXURZHPEJYLPGK-KBPBESRZSA-N
  • C: InChI=1S/C13H14N2O3/c1-6-11-10(16)3-2-8-12(11)7(5-14-8)4-9(15-6)13(17)18/h2-3,5-6,9,14-16H,4H2,1H3,(H,17,18)/t6-,9+/m1/s1
    Key: OGKMUYSVGRXIOH-MUWHJKNJSA-N
  • D: InChI=1S/C13H14N2O3/c1-6-11-10(16)3-2-8-12(11)7(5-14-8)4-9(15-6)13(17)18/h2-3,5-6,9,14-16H,4H2,1H3,(H,17,18)/t6-,9-/m0/s1
    Key: OGKMUYSVGRXIOH-RCOVLWMOSA-N
  • E: InChI=1S/C13H14N2O3/c1-6-12-9(5-11(14-6)13(17)18)8-4-7(16)2-3-10(8)15-12/h2-4,6,11,14-16H,5H2,1H3,(H,17,18)/t6-,11+/m1/s1
    Key: WYQWRMWMBQUYSD-KBUNVGBDSA-N
  • F: InChI=1S/C17H21N3O5/c1-7(18-6-13(22)23)14-12(21)4-3-10-15(14)9-5-11(17(24)25)19-8(2)16(9)20-10/h3-4,7-8,11,18-21H,5-6H2,1-2H3,(H,22,23)(H,24,25)/t7-,8+,11+/m1/s1
    Key: IIUWIOFAHFMFDU-FYBVGQRMSA-N
  • A: C1[C@H](N[C@@H](C2=C1C3=C(N2)C=CC(=C3)O)CC4=CN=CN4)C(=O)O
  • B: C1[C@H](N[C@H](C2=C1C3=C(N2)C=CC(=C3)O)CC4=CN=CN4)C(=O)O
  • C: C[C@@H]1C2=C(C=CC3=C2C(=CN3)C[C@H](N1)C(=O)O)O
  • D: C[C@H]1C2=C(C=CC3=C2C(=CN3)C[C@H](N1)C(=O)O)O
  • E: C[C@@H]1C2=C(C[C@H](N1)C(=O)O)C3=C(N2)C=CC(=C3)O
  • F: C[C@H]1C2=C(C[C@H](N1)C(=O)O)C3=C(N2)C=CC(=C3[C@@H](C)NCC(=O)O)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chemical structures
hyrtioreticulin A
hyrtioreticulin B
hyrtioreticulin C
hyrtioreticulin D
hyrtioreticulin E
hyrtioreticulin F

References
  1. Yamanokuchi, Rumi; Imada, Kumiko; Miyazaki, Mitsue; Kato, Hikaru; Watanabe, Tadashi; Fujimuro, Masahiro; Saeki, Yasushi; Yoshinaga, Sosuke; Terasawa, Hiroaki; Iwasaki, Noriyuki; Rotinsulu, Henki (2012-07-15). "Hyrtioreticulins A–E, indole alkaloids inhibiting the ubiquitin-activating enzyme, from the marine sponge Hyrtios reticulatus". Bioorganic & Medicinal Chemistry. 20 (14): 4437–4442. doi:10.1016/j.bmc.2012.05.044. ISSN 0968-0896. PMID 22695182.
  2. Imada, Kumiko; Sakai, Eriko; Kato, Hikaru; Kawabata, Tetsuro; Yoshinaga, Sosuke; Nehira, Tatsuo; Terasawa, Hiroaki; Tsukamoto, Sachiko (2013). "Reticulatins A and B and hyrtioreticulin F from the marine sponge Hyrtios reticulatus". Tetrahedron. 69 (34): 7051–7055. doi:10.1016/j.tet.2013.06.043.
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