Hyrtioreticulin - Misplaced Pages

Series of chemical substances

Hyrtioreticulin
Names
IUPAC name A: (1R,3S)-6-hydroxy-1-(1H-imidazol-5-ylmethyl)-2,3,4,9-tetrahydro-1H-pyridoindole-3-carboxylic acid B: (1S,3S)-6-hydroxy-1-(1H-imidazol-5-ylmethyl)-2,3,4,9-tetrahydro-1H-pyridoindole-3-carboxylic acid C: (9R,11S)-7-hydroxy-9-methyl-3,10-diazatricyclotrideca-1,4(13),5,7-tetraene-11-carboxylic acid D: (9S,11S)-7-hydroxy-9-methyl-3,10-diazatricyclotrideca-1,4(13),5,7-tetraene-11-carboxylic acid E: (1R,3S)-6-hydroxy-1-methyl-2,3,4,9-tetrahydro-1H-pyridoindole-3-carboxylic acid F: (1S,3S)-5--6-hydroxy-1-methyl-2,3,4,9-tetrahydro-1H-pyridoindole-3-carboxylic acid
Identifiers
CAS Number	E: 42438-96-0
3D model (JSmol)	A: Interactive image B: Interactive image C: Interactive image D: Interactive image E: Interactive image F: Interactive image
ChEMBL	A: ChEMBL2046768 B: ChEMBL2046769 C: ChEMBL2046770 D: ChEMBL2046771 E: ChEMBL2046772
ChemSpider	A: 28507649 B: 28505724 C: 28505725 D: 28530737 E: 28530738
PubChem CID	A: 70694527 B: 70684035 C: 70686170 D: 70686171 E: 70686172 F: 72197062
InChI 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/s1Key: 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/s1Key: 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/s1Key: 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/s1Key: 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/s1Key: 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/s1Key: IIUWIOFAHFMFDU-FYBVGQRMSA-N
SMILES A: C1(N(C2=C1C3=C(N2)C=CC(=C3)O)CC4=CN=CN4)C(=O)O B: C1(N(C2=C1C3=C(N2)C=CC(=C3)O)CC4=CN=CN4)C(=O)O C: C1C2=C(C=CC3=C2C(=CN3)C(N1)C(=O)O)O D: C1C2=C(C=CC3=C2C(=CN3)C(N1)C(=O)O)O E: C1C2=C(C(N1)C(=O)O)C3=C(N2)C=CC(=C3)O F: C1C2=C(C(N1)C(=O)O)C3=C(N2)C=CC(=C3(C)NCC(=O)O)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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

Chemical structures

hyrtioreticulin A	hyrtioreticulin B	hyrtioreticulin C
hyrtioreticulin D	hyrtioreticulin E	hyrtioreticulin F

References

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.
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" (PDF). Tetrahedron. 69 (34): 7051–7055. doi:10.1016/j.tet.2013.06.043.

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