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MedKoo Cat#: 412920 | Name: Cinodine hydrochloride

Description:

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

Cinodine hydrochloride is a glycocinnamoylspermidine antibiotic; gyrase inhibitor found in Nocardia.

Chemical Structure

Cinodine hydrochloride
Cinodine hydrochloride
CAS#68782-58-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 412920

Name: Cinodine hydrochloride

CAS#: 68782-58-1 (HCl)

Chemical Formula: C74H122Cl6N24O28

Exact Mass: 0.0000

Molecular Weight: 2008.63

Elemental Analysis: C, 44.25; H, 6.12; Cl, 10.59; N, 16.74; O, 22.30

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 hydrochloride; Cinodine HCl; Antibiotic BM 123gamma hydrochloride; Cinodine. gamma (sub2) hydrochloride
IUPAC/Chemical Name
(2R,3S,4R,5R,6R)-6-(4-((E)-3-((3-((4-aminobutyl)amino)propyl)amino)-3-oxoprop-1-en-1-yl)phenoxy)-5-((diaminomethylene)amino)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl ((2S,3R,4R,5R)-4-hydroxy-5-(((3aS,6S,7R,7aR)-2-oxo-7-ureidohexahydro-2H-pyrano[4,3-d]oxazol-6-yl)oxy)-3-ureidotetrahydro-2H-pyran-2-yl)carbamate compound with (2R,3S,4R,5R,6R)-6-(4-((E)-3-((3-((4-aminobutyl)amino)propyl)amino)-3-oxoprop-1-en-1-yl)phenoxy)-5-((diaminomethylene)amino)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl ((2S,3R,4R,5R)-5-(((3aR,4S,7S,7aR)-3-carbamoyl-7-hydroxy-2-oxooctahydropyrano[3,4-d]imidazol-4-yl)oxy)-4-hydroxy-3-ureidotetrahydro-2H-pyran-2-yl)carbamate (1:1) hexahydrochloride
InChi Key
LHQGDNLYUSMNNI-BTFLTBNJSA-N
InChi Code
InChI=1S/2C37H58N12O14.6ClH/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);6*1H/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](OC(N[C@@H]2[C@H](NC(N)=O)[C@@H](O)[C@H](O[C@H]3[C@H](NC(N)=O)[C@@H]4[C@H](OC(N4)=O)CO3)CO2)=O)[C@H](O)[C@@H](/N=C(N)\N)[C@@H](OC5=CC=C(/C=C/C(NCCCNCCCCN)=O)C=C5)O1.C[C@@H]6[C@@H](OC(N[C@@H]7[C@H](NC(N)=O)[C@@H](O)[C@H](O[C@H]8[C@H]9[C@@H](NC(N9C(N)=O)=O)[C@H](O)CO8)CO7)=O)[C@H](O)[C@@H](/N=C(N)\N)[C@@H](OC%10=CC=C(/C=C/C(NCCCNCCCCN)=O)C=C%10)O6.Cl.Cl.Cl.Cl.Cl.Cl
Appearance
Solid powder
Purity
Mixture of Cinodine I HCl and Cinodine II HCl
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 2,008.63 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: Chiu SH, Fiala R, Bullock MW. Biosynthesis of the spermidine moiety of glycocinnamoylspermidine antibiotic cinodine. J Antibiot (Tokyo). 1984 Sep;37(9):1079-81. doi: 10.7164/antibiotics.37.1079. PMID: 6501105. 2: 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. PMID: 24398301. 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. doi: 10.7164/antibiotics.37.1000. PMID: 6501101. 4: Greenstein M, Speth JL, Maiese WM. Mechanism of action of cinodine, a glycocinnamoylspermidine antibiotic. Antimicrob Agents Chemother. 1981 Oct;20(4):425-32. doi: 10.1128/aac.20.4.425. PMID: 6177279; PMCID: PMC181719. 5: Hooper DC. Bacterial topoisomerases, anti-topoisomerases, and anti- topoisomerase resistance. Clin Infect Dis. 1998 Aug;27 Suppl 1:S54-63. doi: 10.1086/514923. PMID: 9710672. 6: 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. PMID: 23730361; PMCID: PMC3424198. 7: 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. doi: 10.1128/aac.34.7.1450. PMID: 2167040; PMCID: PMC176000. 8: 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. doi: 10.7164/antibiotics.42.538. PMID: 2498268. 9: 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. doi: 10.7164/antibiotics.42.527. PMID: 2498266. 10: 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. doi: 10.7164/antibiotics.37.1382. PMID: 6511665.