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MedKoo Cat#: 599078 | Name: Cinodine free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cinodine (free base) is a glycocinnamoylspermidine antibiotic; gyrase inhibitor found in Nocardia.

Chemical Structure

Cinodine free base
Cinodine free base
CAS#52932-64-6 (free base)

Theoretical Analysis

MedKoo Cat#: 599078

Name: Cinodine free base

CAS#: 52932-64-6 (free base)

Chemical Formula: C74H116N24O28

Exact Mass: 0.0000

Molecular Weight: 1789.88

Elemental Analysis: C, 49.66; H, 6.53; N, 18.78; O, 25.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
68782-58-1 (HCl) 60830-75-3 (II) 60830-76-4 (I) 52932-64-6 (free base)
Synonym
Cinodine; BM 123 gamma; BM-123 gamma; BM123 gamma; LL-BM 123 gamma; Antibiotic BM 123 gamma;
IUPAC/Chemical Name
[(2R,3S,4R,5R,6R)-6-[4-[(E)-3-[3-(4-aminobutylamino)propylamino]-3-oxoprop-1-enyl]phenoxy]-5-(diaminomethylideneamino)-4-hydroxy-2-methyloxan-3-yl] N-[(2S,3R,4R,5R)-5-[[(3aS,6S,7R,7aR)-7-(carbamoylamino)-2-oxo-1,3a,4,6,7,7a-hexahydropyrano[4,3-d][1,3]oxazol-6-yl]oxy]-3-(carbamoylamino)-4-hydroxyoxan-2-yl]carbamate;[(2R,3S,4R,5R,6R)-6-[4-[(E)-3-[3-(4-aminobutylamino)propylamino]-3-oxoprop-1-enyl]phenoxy]-5-(diaminomethylideneamino)-4-hydroxy-2-methyloxan-3-yl] N-[(2S,3R,4R,5R)-5-[[(3aR,4S,7S,7aR)-3-carbamoyl-7-hydroxy-2-oxo-1,3a,4,6,7,7a-hexahydropyrano[3,4-d]imidazol-4-yl]oxy]-3-(carbamoylamino)-4-hydroxyoxan-2-yl]carbamate
InChi Key
RQOZAAMYXJZOBF-KCPRPGGYSA-N
InChi Code
InChI=1S/2C37H58N12O14/c1-17-29(28(53)25(45-33(39)40)31(60-17)61-19-8-5-18(6-9-19)7-10-22(51)44-14-4-13-43-12-3-2-11-38)63-37(57)48-30-24(46-34(41)54)27(52)21(16-58-30)62-32-26-23(20(50)15-59-32)47-36(56)49(26)35(42)55;1-17-29(28(52)26(45-33(39)40)32(59-17)60-19-8-5-18(6-9-19)7-10-22(50)44-14-4-13-43-12-3-2-11-38)63-37(56)49-30-25(47-35(42)54)27(51)21(16-57-30)61-31-24(46-34(41)53)23-20(15-58-31)62-36(55)48-23/h5-10,17,20-21,23-32,43,50,52-53H,2-4,11-16,38H2,1H3,(H2,42,55)(H,44,51)(H,47,56)(H,48,57)(H4,39,40,45)(H3,41,46,54);5-10,17,20-21,23-32,43,51-52H,2-4,11-16,38H2,1H3,(H,44,50)(H,48,55)(H,49,56)(H4,39,40,45)(H3,41,46,53)(H3,42,47,54)/b2*10-7+/t17-,20-,21-,23+,24-,25-,26-,27+,28-,29-,30+,31-,32+;17-,20-,21-,23+,24-,25-,26-,27+,28-,29-,30+,31+,32-/m11/s1
SMILES Code
C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=CC=C(C=C2)/C=C/C(=O)NCCCNCCCCN)N=C(N)N)O)OC(=O)N[C@@H]3[C@@H]([C@H]([C@@H](CO3)O[C@H]4[C@@H]([C@@H]5[C@@H](CO4)OC(=O)N5)NC(=O)N)O)NC(=O)N.C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=CC=C(C=C2)/C=C/C(=O)NCCCNCCCCN)N=C(N)N)O)OC(=O)N[C@@H]3[C@@H]([C@H]([C@@H](CO3)O[C@H]4[C@H]5[C@H]([C@@H](CO4)O)NC(=O)N5C(=O)N)O)NC(=O)N
Appearance
Solid powder
Purity
Mixture of Cinodine I and Cinodine II
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,789.88 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.

Recalculate based on batch purity %
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: Greenstein M, Speth JL, Maiese WM. Mechanism of action of cinodine, a glycocinnamoylspermidine antibiotic. Antimicrob Agents Chemother. 1981 Oct;20(4):425-32. PubMed PMID: 6177279; PubMed Central PMCID: PMC181719. 2: Chiu SH, Fiala R, Kennett R, Wozniak L, Bullock MW. Biosynthesis of the glycocinnamoylspermidine antibiotic, cinodine. J Antibiot (Tokyo). 1984 Sep;37(9):1000-6. PubMed PMID: 6501101. 3: Osburne MS, Maiese WM, Greenstein M. In vitro inhibition of bacterial DNA gyrase by cinodine, a glycocinnamoylspermidine antibiotic. Antimicrob Agents Chemother. 1990 Jul;34(7):1450-2. PubMed PMID: 2167040; PubMed Central PMCID: PMC176000. 4: Osburne MS. Characterization of a cinodine-resistant mutant of Escherichia coli. J Antibiot (Tokyo). 1995 Nov;48(11):1359-61. PubMed PMID: 8557583. 5: Chen RH, Whittern DN, Buko AM, McAlpine JB. Coumamidines, new broad spectrum antibiotics of the cinodine type. II. Isolation and structural elucidation. J Antibiot (Tokyo). 1989 Apr;42(4):533-7. PubMed PMID: 2498267. 6: Jackson M, Karwowski JP, Theriault RJ, Kohl WL, Humphrey PE, Sunga GN, Swanson SJ, Villarreal RM. Coumamidines, new broad spectrum antibiotics of the cinodine type. I. Discovery, taxonomy of the producing organism and fermentation. J Antibiot (Tokyo). 1989 Apr;42(4):527-32. PubMed PMID: 2498266. 7: Tsou HR, Fiala RR, Mowery PC, Bullock MW. Biosynthesis of the spermidine and guanidino units in the glycocinnamoylspermidine antibiotic cinodine. J Antibiot (Tokyo). 1984 Nov;37(11):1382-7. PubMed PMID: 6511665. 8: Chiu SH, Fiala R, Bullock MW. Biosynthesis of the spermidine moiety of glycocinnamoylspermidine antibiotic cinodine. J Antibiot (Tokyo). 1984 Sep;37(9):1079-81. PubMed PMID: 6501105. 9: McKay MJ, Nguyen HM. Recent developments in glycosyl urea synthesis. Carbohydr Res. 2014 Feb 19;385:18-44. doi: 10.1016/j.carres.2013.08.007. Epub 2013 Aug 19. Review. PubMed PMID: 24398301. 10: Fernandes PB, Swanson RN, Hardy DJ, Hanson CW, McDaniel D, Beyer J, Chen RH. Coumamidines, new broad spectrum antibiotics of the cinodine type. III. Microbiologic activity of coumamidine gamma 1. J Antibiot (Tokyo). 1989 Apr;42(4):538-41. PubMed PMID: 2498268. 11: Hooper DC. Bacterial topoisomerases, anti-topoisomerases, and anti-topoisomerase resistance. Clin Infect Dis. 1998 Aug;27 Suppl 1:S54-63. Review. PubMed PMID: 9710672. 12: Singh V, Chaudhary DK, Mani I. Gene network analysis of Aeromonas hydrophila for novel drug target discovery. Syst Synth Biol. 2012 Jun;6(1-2):23-30. doi: 10.1007/s11693-012-9093-z. Epub 2012 May 22. PubMed PMID: 23730361; PubMed Central PMCID: PMC3424198. 13: McGahren WJ, Barbatschi F, Kuck NA, Morton GO, Hardy B, Ellestad GA. Medical Research Division of American Cyanamid Company, Lederle Laboratories, Pearl River, NY. J Antibiot (Tokyo). 1982 Jul;35(7):794-9. PubMed PMID: 7174533. 14: Servis NA, Nichols S, Adams JC. Development of a direct viable count procedure for some gram-positive bacteria. Lett Appl Microbiol. 1995 Apr;20(4):237-9. PubMed PMID: 7766118. 15: Ellestad GA. From natural products to bioorganic chemistry. What's next? J Med Chem. 2006 Nov 16;49(23):6627-34. PubMed PMID: 17154489.