Cinodine I

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

MedKoo CAT#: 599084

CAS#: 60830-76-4 (I)

Description: Cinodine I is a glycocinnamoylspermidine antibiotic.

Chemical Structure

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Cinodine I
CAS# 60830-76-4 (I)
Instruction

Theoretical Analysis

MedKoo Cat#: 599084
Name: Cinodine I
CAS#: 60830-76-4 (I)
Chemical Formula: C37H59N13O13
Exact Mass: 893.44
Molecular Weight: 893.950
Elemental Analysis: C, 49.71; H, 6.65; N, 20.37; O, 23.27

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Related CAS #: 68782-58-1 (HCl)   60830-75-3 (II)   60830-76-4 (I)   52932-64-6 (free base)    

Synonym: Cinodine I; LL-BM 123 (sub gamma 1); LL-BM-123-C1; BM-123-G''1;

IUPAC/Chemical Name: (3aR,4S,7S,7aR)-4-(((3R,4R,5R,6S)-6-(3-((2R,3S,4S,5R,6R)-6-(4-((E)-3-((3-((4-aminobutyl)amino)propyl)amino)-3-oxoprop-1-en-1-yl)phenoxy)-5-guanidino-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)ureido)-4-hydroxy-5-ureidotetrahydro-2H-pyran-3-yl)oxy)-7-hydroxy-2-oxohexahydropyrano[3,4-d]imidazole-3(2H)-carboxamide

InChi Key: DNVZVPOGAWMZMI-FWDCAGJFSA-N

InChi Code: InChI=1S/C37H59N13O13/c1-17-23(29(54)26(45-33(39)40)31(61-17)62-19-8-5-18(6-9-19)7-10-22(52)44-14-4-13-43-12-3-2-11-38)47-36(57)49-30-25(46-34(41)55)28(53)21(16-59-30)63-32-27-24(20(51)15-60-32)48-37(58)50(27)35(42)56/h5-10,17,20-21,23-32,43,51,53-54H,2-4,11-16,38H2,1H3,(H2,42,56)(H,44,52)(H,48,58)(H4,39,40,45)(H3,41,46,55)(H2,47,49,57)/b10-7+/t17-,20-,21-,23-,24+,25-,26-,27-,28+,29+,30+,31-,32+/m1/s1

SMILES Code: C[C@@H]1[C@@H](NC(N[C@@H]2[C@H](NC(N)=O)[C@@H](O)[C@H](O[C@H]3[C@H]4[C@@H](NC(N4C(N)=O)=O)[C@H](O)CO3)CO2)=O)[C@H](O)[C@@H](NC(N)=N)[C@@H](Oc5ccc(/C=C/C(NCCCNCCCCN)=O)cc5)O1

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: >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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 893.95 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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.

2: 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.

3: 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.

4: 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.

5: Osburne MS. Characterization of a cinodine-resistant mutant of Escherichia coli. J Antibiot (Tokyo). 1995 Nov;48(11):1359-61. PubMed PMID: 8557583.

6: 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.

7: 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.

8: 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.

9: 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.

10: 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.

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: 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.

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.