Flavofosfolipol

Synopsis, Chemistry

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Also known as: Flavofosfolipol, Gainpro, Menomycin, Bambermycine [inn-french], Bambermycinum [inn-latin], Bambermicina [inn-spanish]

Molecular Formula

C₇₀H₁₀₉N₄O₃₅P

Molecular Weight

1597.6 g/mol

InChI Key

FUIOWSNNCWZETH-NAMXWVJMSA-N

Antibiotic complex obtained from Streptomyces bambergiensis containing mainly Moenomycins A and C. They are used as feed additives and growth promoters for poultry, swine, and cattle.

1 2D Structure

Flavofosfolipol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4-carbamoyloxy-3-hydroxy-6-[hydroxy-[(2R)-2-hydroxy-3-oxo-3-[(3E,7E,14E)-4,9,9,15,19-pentamethyl-12-methylideneicosa-3,7,14,18-tetraenoxy]propoxy]phosphoryl]oxy-3-methyloxane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C70H109N4O35P/c1-31(2)16-14-18-33(4)20-21-34(5)24-26-69(9,10)25-13-12-17-32(3)19-15-27-97-62(92)40(80)29-99-110(95,96)109-67-57(58(108-68(71)93)70(11,94)59(107-67)61(90)91)106-64-45(73-37(8)77)48(83)55(42(102-64)30-98-65-52(87)49(84)46(81)41(28-75)101-65)104-63-44(72-36(7)76)47(82)54(35(6)100-63)103-66-53(88)50(85)51(86)56(105-66)60(89)74-43-38(78)22-23-39(43)79/h13,16,19-20,25,35,40-42,44-59,63-67,75,78,80-88,94H,5,12,14-15,17-18,21-24,26-30H2,1-4,6-11H3,(H2,71,93)(H,72,76)(H,73,77)(H,74,89)(H,90,91)(H,95,96)/b25-13+,32-19+,33-20+/t35-,40-,41-,42-,44-,45-,46-,47-,48-,49+,50+,51-,52-,53-,54-,55-,56+,57-,58-,59-,63+,64+,65-,66-,67-,70+/m1/s1

2.1.3 InChI Key

FUIOWSNNCWZETH-NAMXWVJMSA-N

2.1.4 Canonical SMILES

CC1C(C(C(C(O1)OC2C(OC(C(C2O)NC(=O)C)OC3C(C(C(OC3OP(=O)(O)OCC(C(=O)OCCC=C(C)CCC=CC(C)(C)CCC(=C)CC=C(C)CCC=C(C)C)O)C(=O)O)(C)O)OC(=O)N)COC4C(C(C(C(O4)CO)O)O)O)NC(=O)C)O)OC5C(C(C(C(O5)C(=O)NC6=C(CCC6=O)O)O)O)O

2.1.5 Isomeric SMILES

C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)NC(=O)C)O[C@@H]3[C@H]([C@]([C@H](O[C@@H]3OP(=O)(O)OC[C@H](C(=O)OCC/C=C(\C)/CC/C=C/C(C)(C)CCC(=C)C/C=C(\C)/CCC=C(C)C)O)C(=O)O)(C)O)OC(=O)N)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)NC(=O)C)O)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)C(=O)NC6=C(CCC6=O)O)O)O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Bambermycin

2. Flavomycin

3. Flavomycins

4. Flavophospholipol

5. Flavophospholipols

6. Menomycin

7. Moenomycins

2.2.2 Depositor-Supplied Synonyms

1. Flavofosfolipol

2. Gainpro

3. Menomycin

4. Bambermycine [inn-french]

5. Bambermycinum [inn-latin]

6. Bambermicina [inn-spanish]

7. Bambermycin [inn]

8. Einecs 234-246-7

9. Unii-pp922a42v2

10. Pp922a42v2

11. Db11377

12. Ncgc00181293-01

13. Antibiotic Complex, Containing Mainly Moenomycin A And C, Obtained From Cultures Of Streptomyces Bambergiensis, Or The Same Substance Obtained By Any Other Means

14. Antibiotic Complex, Containing Mainly Moenomycin A And C, Obtained From Cultures Of Streptomyces Bambergiensis, Or The Same Substance Obtained By Any Other Means. Bambermycin

2.3 Create Date

2006-04-28

3 Chemical and Physical Properties

Molecular Formula	C₇₀H₁₀₉N₄O₃₅P
Molecular Weight	1597.6 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	18
Hydrogen Bond Acceptor Count	35
Rotatable Bond Count	39
Exact Mass	1596.6609982 g/mol
Monoisotopic Mass	1596.6609982 g/mol
Topological Polar Surface Area	602 Å²
Heavy Atom Count	110
Formal Charge	0
Complexity	3390
Isotope Atom Count	0
Defined Atom Stereocenter Count	26
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1