WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 413438
CAS#: 79553-45-0
Description: Cytovaricin is a novel antibiotic from Streptomyces sp. No. H-230.
MedKoo Cat#: 413438
Name: Cytovaricin
CAS#: 79553-45-0
Chemical Formula: C47H80O16
Exact Mass: 900.5446
Molecular Weight: 901.14
Elemental Analysis: C, 62.64; H, 8.95; O, 28.41
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Synonym: Cytovaricin; BRN4226438; BRN-4226438; BRN 4226438
IUPAC/Chemical Name: COMPOUND SUMMARY CID 6436235 PubChem CID 6436235 Structure CID 6436235_small.png Find Similar Structures Molecular Formula C47H80O16 Synonyms Cytovaricin NSC 349622 BRN 4226438 H-230 79553-45-0 More... Molecular Weight 901.1 g/mol Dates Modify 2021-02-27 Create 2006-04-28 1Structures HelpNew Window 1.12D Structure HelpNew Window Find Similar Structures Get Image Download Chemical Structure Depiction CID 6436235.png Full screen Zoom in Zoom out PubChem 1.23D Status HelpNew Window Conformer generation is disallowed since too many atoms PubChem 2Names and Identifiers HelpNew Window 2.1Computed Descriptors HelpNew Window 2.1.1IUPAC Name HelpNew Window (1S,3S,5'S,6S,6'S,8S,9E,14R,15R,16S,17R,18S,19S,20R,21E,25S,27R,29R)-3,14,15,17,19,20-hexahydroxy-6'-[(2R)-2-hydroxybutyl]-16-[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5',6,14,18,20,29-hexamethylspiro[4,24,28-trioxatricyclo[23.3.1.03,8]nonacosa-9,21-diene-27,2'-oxane]-23-one
InChi Key: NORZLTHXFWGSAT-TUHQYYMQSA-N
InChi Code: InChI=1S/C47H80O16/c1-10-32(48)21-33-27(3)15-19-46(62-33)23-35-28(4)36(63-46)24-47(56)31(20-26(2)25-58-47)14-12-11-13-17-44(7,54)43(53)41(61-38-22-34(57-9)40(51)30(6)59-38)39(50)29(5)42(52)45(8,55)18-16-37(49)60-35/h12,14,16,18,26-36,38-43,48,50-56H,10-11,13,15,17,19-25H2,1-9H3/b14-12+,18-16+/t26-,27-,28-,29-,30+,31+,32+,33-,34-,35-,36-,38-,39+,40+,41-,42-,43+,44+,45+,46+,47-/m0/s1
SMILES Code: CC[C@H](C[C@@H]1O[C@]2(C[C@@H]3OC(/C=C/[C@@](O)([C@H]([C@H]([C@H]([C@@H]([C@H]([C@](O)(CCC/C=C/[C@@H]4C[C@@H](CO[C@]4(C[C@@H]([C@H]3C)O2)O)C)C)O)O[C@H]5C[C@@H]([C@@H]([C@H](O5)C)O)OC)O)C)O)C)=O)CC[C@@H]1C)O
Appearance: Solid powder
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: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
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
The following data is based on the product molecular weight 901.14 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: Yamashita N, Kazuo SY, Kitamura M, Wakao H, Furihata K, Furihata K, Hayakawa Y, Miyajima A, Seto H. Cytovaricin B, a new inhibitor of JAK-STAT signal transduction produced by Streptomyces torulosus. J Antibiot (Tokyo). 1997 May;50(5):440-2. doi: 10.7164/antibiotics.50.440. PMID: 9207915.
2: Kihara T, Kusakabe H, Nakamura G, Sakurai T, Isono K. Cytovaricin, a novel antibiotic. J Antibiot (Tokyo). 1981 Aug;34(8):1073-4. doi: 10.7164/antibiotics.34.1073. PMID: 7319923.
3: Kihara T, Ubukata M, Uzawa J, Isono K. Biosynthesis and 13C NMR assignment of cytovaricin, a neutral macrolide antibiotic. J Antibiot (Tokyo). 1989 Jun;42(6):919-25. doi: 10.7164/antibiotics.42.919. PMID: 2737951.
4: Kihara T, Isono K. The absolute configuration of cytovaricin: isolation of methyl beta-D-cymaroside by methanolysis. J Antibiot (Tokyo). 1983 Sep;36(9):1236. doi: 10.7164/antibiotics.36.1236. PMID: 6630081.
5: Trost BM, O'Boyle BM, Hund D. Total synthesis and stereochemical assignment of (-)-ushikulide A. J Am Chem Soc. 2009 Oct 21;131(41):15061-74. doi: 10.1021/ja906056v. PMID: 19775093; PMCID: PMC2791109.
6: Salomon AR, Voehringer DW, Herzenberg LA, Khosla C. Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase. Chem Biol. 2001 Jan;8(1):71-80. doi: 10.1016/s1074-5521(00)00057-0. PMID: 11182320.
7: Salomon AR, Zhang Y, Seto H, Khosla C. Structure-activity relationships within a family of selectively cytotoxic macrolide natural products. Org Lett. 2001 Jan 11;3(1):57-9. doi: 10.1021/ol006767d. PMID: 11429871.
8: Kirst HA, Mynderse JS, Martin JW, Baker PJ, Paschal JW, Rios Steiner JL, Lobkovsky E, Clardy J. Structure of the spiroketal-macrolide ossamycin. J Antibiot (Tokyo). 1996 Feb;49(2):162-7. doi: 10.7164/antibiotics.49.162. PMID: 8621357.
9: Kirst HA, Larsen SH, Paschal JW, Occolowitz JL, Creemer LC, Steiner JL, Lobkovsky E, Clardy J. Structure of the new spiroketal-macrolide A82548A. J Antibiot (Tokyo). 1995 Sep;48(9):990-6. doi: 10.7164/antibiotics.48.990. PMID: 7592067.
10: Salomon AR, Voehringer DW, Herzenberg LA, Khosla C. Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F(0)F(1)-ATPase. Proc Natl Acad Sci U S A. 2000 Dec 19;97(26):14766-71. doi: 10.1073/pnas.97.26.14766. PMID: 11121076; PMCID: PMC18993.
