Flavomycin
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Basic Info
| Common Name | Flavomycin(F06210) |
| 2D Structure | |
| FRCD ID | F06210 |
| CAS Number | 11015-37-5 |
| PubChem CID | 46783781 |
| Formula | C69H107N4O35P |
| IUPAC Name | (2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S)-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-6-[[(2R)-2-carboxy-2-[(2E,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]ethoxy]-hydroxyphosphoryl]oxy-3-hydroxy-3-methyloxane-2-carboxylic acid |
| InChI Key | PERZMHJGZKHNGU-XIGAONJHSA-N |
| InChI | InChI=1S/C69H107N4O35P/c1-30(2)15-14-17-31(3)18-19-33(5)22-25-68(9,10)24-13-12-16-32(4)23-26-96-41(60(88)89)29-98-109(94,95)108-66-56(57(107-67(70)92)69(11,93)58(106-66)61(90)91)105-63-44(72-36(8)76)47(81)54(40(101-63)28-97-64-51(85)48(82)45(79)39(27-74)100-64)103-62-43(71-35(7)75)46(80)53(34(6)99-62)102-65-52(86)49(83)50(84)55(104-65)59(87)73-42-37(77)20-21-38(42)78/h13,15,18,23-24,34,39-41,43-58,62-66,74,77,79-86,93H,5,12,14,16-17,19-22,25-29H2,1-4,6-11H3,(H2,70,92)(H,71,75)(H,72,76)(H,73,87)(H,88,89)(H,90,91)(H,94,95)/b24-13+,31-18+,32-23+/t34?,39-,40-,41-,43-,44-,45-,46-,47-,48+,49+,50-,51-,52-,53-,54-,55+,56-,57-,58-,62+,63+,64-,65-,66-,69+/m1/s1 |
| Canonical SMILES | CC1C(C(C(C(O1)OC2C(OC(C(C2O)NC(=O)C)OC3C(C(C(OC3OP(=O)(O)OCC(C(=O)O)OCC=C(C)CCC=CC(C)(C)CCC(=C)CC=C(C)CCC=C(C)C)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 |
| Isomeric SMILES | CC1[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)O)OC/C=C(\C)/CC/C=C/C(C)(C)CCC(=C)C/C=C(\C)/CCC=C(C)C)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 |
| Synonyms |
(2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S)-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-
Flavomycin
11015-37-5
Moenomycin complex
MolPort-006-823-804
C69H107N4O35P
AKOS016339637
KS-5173
I020
015F375
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Terpene glycosides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Terpene glycosides |
| Alternative Parents |
|
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Oligosaccharide phosphate - Oligosaccharide - Terpene glycoside - Fatty acyl glycoside - N-acyl-alpha-hexosamine - Glucuronic acid or derivatives - Glycosyl compound - O-glycosyl compound - Monocyclic monoterpenoid - Monoterpenoid - Glyceric_acid - Dialkyl phosphate - Alkyl phosphate - Dicarboxylic acid or derivatives - Pyran - Fatty acyl - Phosphoric acid ester - Oxane - Organic phosphoric acid derivative - Tertiary alcohol - Vinylogous acid - Cyclic ketone - Ketone - Secondary alcohol - Propargyl-type 1,3-dipolar organic compound - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Organic 1,3-dipolar compound - Ether - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Imine - Carbonyl group - Organic oxide - Hydrocarbon derivative - Alcohol - Primary alcohol - Aldehyde - Organooxygen compound - Organonitrogen compound - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 1583.582 |
| Hydrogen Bond Donor Count | 18 |
| Hydrogen Bond Acceptor Count | 35 |
| Rotatable Bond Count | 38 |
| Complexity | 3370 |
| Monoisotopic Mass | 1582.645 |
| Exact Mass | 1582.645 |
| XLogP | -0.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 109 |
| Defined Atom Stereocenter Count | 25 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9264 |
| Human Intestinal Absorption | HIA- | 0.9810 |
| Caco-2 Permeability | Caco2- | 0.6654 |
| P-glycoprotein Substrate | Substrate | 0.7291 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7255 |
| Non-inhibitor | 0.8652 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9591 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6217 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7909 |
| CYP450 2D6 Substrate | Non-substrate | 0.8199 |
| CYP450 3A4 Substrate | Substrate | 0.6130 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7619 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7595 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8819 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7166 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5635 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8611 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9419 |
| Non-inhibitor | 0.7475 | |
| AMES Toxicity | Non AMES toxic | 0.6318 |
| Carcinogens | Non-carcinogens | 0.9191 |
| Fish Toxicity | High FHMT | 0.9922 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9917 |
| Honey Bee Toxicity | High HBT | 0.5285 |
| Biodegradation | Not ready biodegradable | 0.9805 |
| Acute Oral Toxicity | III | 0.5840 |
| Carcinogenicity (Three-class) | Non-required | 0.5100 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1970 | LogS |
| Caco-2 Permeability | -0.3479 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6936 | LD50, mol/kg |
| Fish Toxicity | 1.2678 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5660 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Poultry,Eggs | Japan | 0.02ppm | |||
| Chicken,Eggs | Japan | 0.02ppm | |||
| Chicken,Kidney | Japan | 0.03ppm | |||
| Chicken,Edible Offal | Japan | 0.03ppm | |||
| Chicken,Liver | Japan | 0.03ppm | |||
| Chicken,Fat | Japan | 0.03ppm | |||
| Chicken,Muscle | Japan | 0.03ppm | |||
| Milk | Japan | 0.01ppm | |||
| Pig,Edible Offal | Japan | 0.01ppm | |||
| Cattle,Edible Offal | Japan | 0.01ppm | |||
| Pig,Kidney | Japan | 0.01ppm | |||
| Cattle,Kidney | Japan | 0.01ppm | |||
| Pig,Liver | Japan | 0.01ppm | |||
| Cattle,Liver | Japan | 0.01ppm | |||
| Pig,Fat | Japan | 0.01ppm | |||
| Cattle,Fat | Japan | 0.01ppm | |||
| Pig,Muscle | Japan | 0.01ppm | |||
| Cattle,Muscle | Japan | 0.01ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effects of Lactobacillus acidophilus dietary supplementation on the performance, intestinal barrier function, rectal microflora and serum immune function in weaned piglets challenged with Escherichia coli lipopolysaccharide. | Antonie Van Leeuwenhoek | 2015 Apr | 25577203 |