Synonym
Panepophenanthrin;
IUPAC/Chemical Name
(1aS,1bR,1b1S,3aS,5aS,6aS,7R,7aS,7bS,8R,8aS)-1b,7,8-trihydroxy-1b1-((E)-3-hydroxy-3-methylbut-1-en-1-yl)-3,3-dimethyl-1a,1b,1b1,3,3a,5a,6a,7,7a,7b,8,8a-dodecahydro-5H-bis(oxireno)[2',3':2,3;2'',3'':6,7]phenanthro[1,10-bc]furan-5-one
InChi Key
WQBRQZUREPTGLI-ODDMXWQNSA-N
InChi Code
1S/C22H28O8/c1-19(2,26)5-6-21-9-7-8-10(13(24)16-15(28-16)12(8)23)11(21)14(25)17-18(29-17)22(21,27)30-20(9,3)4/h5-7,9-11,13-18,24-27H,1-4H3/b6-5+/t9-,10-,11-,13-,14-,15-,16+,17+,18+,21-,22+/m1/s1
SMILES Code
[H][C@@]12C=C3C(=O)[C@H]4O[C@H]4[C@H](O)[C@@]3([H])[C@]5([H])[C@@H](O)[C@@H]6O[C@@H]6[C@](O)(OC1(C)C)[C@]25\C=C\C(C)(C)O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
420.46
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Sekizawa R, Ikeno S, Nakamura H, Naganawa H, Matsui S, Iinuma H, Takeuchi T. Panepophenanthrin, from a mushroom strain, a novel inhibitor of the ubiquitin- activating enzyme. J Nat Prod. 2002 Oct;65(10):1491-3. doi: 10.1021/np020098q. PMID: 12398550.
2: Moses JE, Commeiras L, Baldwin JE, Adlington RM. Total synthesis of panepophenanthrin. Org Lett. 2003 Aug 21;5(17):2987-8. doi: 10.1021/ol0349817. PMID: 12916962.
3: Lei X, Johnson RP, Porco JA Jr. Total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin. Angew Chem Int Ed Engl. 2003 Aug 25;42(33):3913-7. doi: 10.1002/anie.200351862. PMID: 12949867.
4: Li J, Lee D. Application of a tandem metathesis to the synthesis of (+)-panepophenanthrin. Chem Asian J. 2010 Jun 1;5(6):1298-302. doi: 10.1002/asia.200900724. PMID: 20414919.
5: Llanos-López NA, Ebada SS, Vasco-Palacios AM, Sánchez-Giraldo LM, López L, Rojas LF, Mándi A, Kurtán T, Marin-Felix Y. Panapophenanthrin, a Rare Oligocyclic Diterpene from Panus strigellus. Metabolites. 2023 Jul 13;13(7):848. doi: 10.3390/metabo13070848. PMID: 37512554; PMCID: PMC10385786.
6: Matsuzawa M, Kakeya H, Yamaguchi J, Shoji M, Onose R, Osada H, Hayashi Y. Enantio- and diastereoselective total synthesis of (+)-panepophenanthrin, a ubiquitin-activating enzyme inhibitor, and biological properties of its new derivatives. Chem Asian J. 2006 Dec 18;1(6):845-51. doi: 10.1002/asia.200600199. PMID: 17441127.
7: Song JG, Ha LS, Ki DW, Choi DC, Lee IK, Yun BS. Chemical Constituents of the Culture Broth of Panus rudis. Mycobiology. 2021 Dec 6;49(6):604-606. doi: 10.1080/12298093.2021.2004663. PMID: 35035252; PMCID: PMC8725926.
8: Pinkerton DM, Banwell MG, Willis AC. Chemoenzymatic access to versatile epoxyquinol synthons. Org Lett. 2009 Oct 1;11(19):4290-3. doi: 10.1021/ol9016657. PMID: 19743818.
9: Rychnovsky SD. Predicting NMR spectra by computational methods: structure revision of hexacyclinol. Org Lett. 2006 Jun 22;8(13):2895-8. doi: 10.1021/ol0611346. PMID: 16774284.
