Mycoheptin

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

MedKoo CAT#: 463029

CAS#: 12609-89-1 (free)

Description: Mycoheptin is an antifungal antibiotic.


Chemical Structure

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Mycoheptin
CAS# 12609-89-1 (free)

Theoretical Analysis

MedKoo Cat#: 463029
Name: Mycoheptin
CAS#: 12609-89-1 (free)
Chemical Formula: C47H71NO17
Exact Mass: 921.4722
Molecular Weight: 922.075
Elemental Analysis: C, 61.22; H, 7.76; N, 1.52; O, 29.50

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.

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Related CAS #: 12609-89-1 (free); 75442-91-0 (sodium salt)  

Synonym: Antibiotic 281471; Antibiotic 44 VI; Mycoheptyne;

IUPAC/Chemical Name: (1S,3R,4R,7R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,3,4,7,11,17,37-heptahydroxy-15,16,18-trimethyl-9,13-dioxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid

InChi Key: GXLOOVOKGBOVIH-YPBFURFVSA-N

InChi Code: InChI=1S/C47H71NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-31,33-38,40-44,46,49,51-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,33+,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

SMILES Code: C[C@@H]1OC(C[C@@H](CC(C[C@@H](CC[C@H]([C@@H](C[C@@]2(C[C@@H]([C@@H](C(O)=O)[C@@H](O2)C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H]([C@H]([C@H]1C)O)C)O[C@@H]3O[C@@H]([C@H]([C@@H]([C@@H]3O)N)O)C)O)O)O)O)O)=O)O)=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: >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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 922.075 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

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1: Płosiński M, Laskowski T, Sowiński P, Pawlak J. Stereostructure of mycoheptin A(2). Magn Reson Chem. 2012 Dec;50(12):818-22. doi: 10.1002/mrc.3890. Epub 2012 Oct 19. PMID: 23081829.

2: Belakhov VV, Shenin IuD. Izuchenie vozmozhnosti ispol'zovaniia mitselial'nykh otkhodov proizvodstva protivogribkovykh antibiotikov v kachestve prisadok k smazochnym maslam [The possibility of using the mycelial wastes from the production of antifungal antibiotics as additives to lubricating oils]. Antibiot Khimioter. 1997;42(5):35-7. Russian. PMID: 9254586.

3: Shvinka NE, Caffier G. Nystatin-, mycoheptin- and levorin-induced conductance in the membrane of frog skeletal muscle fibres. Eur Biophys J. 1995;24(1):23-30. doi: 10.1007/BF00216827. PMID: 7635090.

4: Shvinka N, Caffier G. Cation conductance and efflux induced by polyene antibiotics in the membrane of skeletal muscle fiber. Biophys J. 1994 Jul;67(1):143-52. doi: 10.1016/S0006-3495(94)80463-1. PMID: 7918981; PMCID: PMC1225343.

5: Bezrukova IP, Malkov MA. Vliianie kharakteristik posevnogo materiala na napravlennost' vtorichnogo sinteza produtsentov novobiotsina i mikogeptina [Effect of inoculum parameters on the specificity of secondary synthesis in cultures producing novobiocin and mycoheptin]. Antibiot Khimioter. 1992 Oct;37(10):24-6. Russian. PMID: 1296528.

6: Bezrukova IP, Malkov MA, Kuzina ZA. Issledovanie biosinteza mikogeptina, mikopentena i zhirnykh kislot v razlichnykh usloviiakh kul'tivirovaniia Streptoverticillium mycoheptinicum shtamm 255 [Study of biosynthesis of mycoheptin, mycopentene and fatty acids by Streptoverticillium mycoheptinicum strain 255 in various conditions of its cultivation]. Antibiot Khimioter. 1992 Feb;37(2):3-5. Russian. PMID: 1514852.

7: Mitrofanova VG, Mirgorodskaia OA, Derzhavets AA, Matveeva ER, Shenin IuD, Morgunova AF. Izuchenie komponentnogo sostava standartnykh obraztsov polienovykh makrolidnykh antibiotikov metodom vysokoéffektivnoĭ zhidkostnoĭ khromatografii i mass-spektrometrii ERIAD [Study of components of standard samples of polyene macrolide antibiotics by the methods of high performance liquid chromatography and SIEAP mass spectrometry]. Antibiot Khimioter. 1991 Oct;36(10):9-11. Russian. PMID: 1805702.

8: Belakhov VV, Vlasenko AIu, Levina AA, Shenin IuD, Rozhkova NG, Smirnova GK. Sravnitel'noe izuchenie fungitsidnoĭ i gerbitsidnoĭ aktivnosti soleĭ polienovykh makrolidnykh antibiotikov [Comparative study of fungicidal and herbicidal activities of salts of polyenic macrolide antibiotics]. Antibiot Khimioter. 1991 Sep;36(9):11-3. Russian. PMID: 1781700.

9: Skosyreva AM, Baklanova OV, Padeĭskaia EN. Patomorfologicheskaia otsenka modeleĭ kandidoznoĭ infektsii mysheĭ, vyzvannoĭ vnutrennym ili vnutrimozgovym zarazheniem [Pathomorphological estimation of models of mouse Candida infection induced by intravenous or intracerebral contamination]. Antibiot Khimioter. 1990 Nov;35(11):29-34. Russian. PMID: 2092635.

10: Kudriavskaia VM, Rudenko AV, Pyrig LA. Lekarstvennaia chuvstvite'lnos't gribov roda Candida u bo'lnykh s zabolevaniiami pochek, poluchaiushchikh immunodepressivnuiu terapiiu [Drug sensitivity of Candida in patients with kidney diseases receiving immunosuppressive therapy]. Antibiot Khimioter. 1989 Oct;34(10):769-73. Russian. PMID: 2619408.

11: Mitrofanova VG, Bol'shakova LO, Bershteĭn EM, Shenin IuD. Izuchenie vliianiia antioksidantov i kompleksonov na stabil'nost' mikrobiologicheskogo standarta mikogeptina [Effect of antioxidants and complexons on the stability of the microbiological standard for mycoheptin]. Antibiot Med Biotekhnol. 1985 Sep;30(9):654-7. Russian. PMID: 4062282.

12: Liubimova LK, Ovnanian KO, Ivanova LN. Protivoamebnoe deĭstvie polienovykh antibiotikov [Anti-amebic effect of polyenic antibiotics]. Antibiot Med Biotekhnol. 1985 Mar;30(3):179-82. Russian. PMID: 2861787.

13: Iakovleva EP, Rozhanskaia TI, Levit ZhD, Selezneva AA, Miasnikova LG. Ingibitor fosfolipazy C iz Streptoverticillium mycoheptinicum [Phospholipase C inhibitor from Streptoverticillium mycoheptinicum]. Prikl Biokhim Mikrobiol. 1984 May-Jun;20(3):349-54. Russian. PMID: 6087312.

14: Lapina IK, Zhukova RA. Auksotrofnye mutanty produtsenta antibiotika mikogeptina Streptoverticillium mycoheptinicum [Auxotrophic mutants of the producer of the antibiotic mycoheptin Streptoverticillium mycoheptinicum]. Antibiotiki. 1983 Jan;28(1):15-8. Russian. PMID: 6830197.

15: Chuenkova MV, Sukhareva NN, Liubimova LK, Egorov NS. Izuchenie chuvstvitel'nosti tripanosomid k polienovym antibiotikam [Trypanosome sensitivity to polyene antibiotics]. Antibiotiki. 1982 Jun;27(6):424-30. Russian. PMID: 7051969.

16: Mitintskiĭ AB, Fradkova TA, Poliak MS. Matematicheskaia model' zonoobrazovaniia s uchetom inaktivatsii polienovykh antibiotikov, diffundiruiushchikh v zarazhennyĭ gel' [Mathematical model of zone formation taking into account the inactivation of polyene antibiotics diffusing into an inoculated gel]. Antibiotiki. 1981 Sep;26(9):676-80. Russian. PMID: 7294759.

17: Etingova NI. Soliubilizatsiia polienovykh antibiotikov soliami zhelchnykh kislot v vodnykh rastvorakh [Polyene antibiotic solubilization by bile acid salts in aqueous solutions]. Antibiotiki. 1981 Jun;26(6):414-9. Russian. PMID: 7271250.

18: Vil'ner LM, Ral'f NM, Finogenova EV, Shneĭder MA, Tereshin IM. Vliianie polienovykh antibiotikov na povyshenie spetsificheskoĭ rezistentnosti, vyzvannoi inaktivirovannymi protivovirusnymi vaktsinami [Effect of polyene antibiotics on the increase in specific resistance due to inactivated antiviral vaccines]. Antibiotiki. 1980 Sep;25(9):669-73. Russian. PMID: 7416734.

19: Iakovleva EP, Kuznetsova OS, Tsyganov VA. Osobennosti obrazovaniia veshchestv, stimuliruiushchikh biosintez levorina, razlichnymi mikoorganizmami [Characteristics of the formation of substances by various microorganisms that stimulate levorin biosynthesis]. Antibiotiki. 1980 Aug;25(8):572-6. Russian. PMID: 7406468.

20: Bol'shakova LO, Gagloshvili VM, Shenin IuD, Bershteĭn EM, Mikhaĭlova MA. Fiziko-khimicheskaia i biologicheskaia kharakteristika komponentov A1 i A2 mikogeptina [Physicochemical and biological characteristics of mycoheptin components A1 and A2]. Antibiotiki. 1980 Jul;25(7):499-503. Russian. PMID: 7406459.