Helvecardin B
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| Category | Antibiotics |
| Catalog number | BBF-01335 |
| CAS | 119979-34-9 |
| Molecular Weight | 1795.58 |
| Molecular Formula | C84H93Cl2N9O31 |
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Description
It is produced by the strain of Pseudonocardia compacta subsp. Helvetica SANK 65185. It is a glycopeptidtic antibiotic. It has strong activity of anti-aerobic and anaerobic gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, but its protective effect against staphylococcus aureus infection in mice is lower than vancomycin.
Specification
| Synonyms | 49-Chloro-7-O-de(α-D-mannopyranosyl)-2'''''-O-methylavoparcin α; Avoparcin alpha, 49-chloro-7-O-de-alpha-D-mannopyranosyl-2C-O-methyl- |
| IUPAC Name | (1S,2R,18R,19R,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-48-[(2S,3R,5S,6R)-3-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-chloro-22-(3-chloro-4-hydroxyphenyl)-19-[[2-[4-(4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl)oxyphenyl]-2-(methylamino)acetyl]amino]-18,32,35,37-tetrahydroxy-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14(47),15,17(46),29(45),30,32,34(39),35,37,49-pentadecaene-40-carboxylic acid |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C7C(=O)NC(C8=C(C(=CC(=C8)O)O)C9=C(C=CC(=C9)C(C(=O)N7)NC(=O)C5NC(=O)C(NC(=O)C(C(C1=CC=C(O4)C=C1)O)NC(=O)C(C1=CC=C(C=C1)OC1C(C(C(C(O1)C)O)O)OC)NC)C1=CC(=C(C=C1)O)Cl)O)C(=O)O)OC1CC(C(C(O1)C)O)N)Cl)CO)O)O)N)O |
| InChI | InChI=1S/C84H93Cl2N9O31/c1-30-65(101)46(87)27-55(117-30)124-72-37-12-19-51(45(86)22-37)122-53-24-38-23-52(73(53)126-84-75(71(107)69(105)54(29-96)123-84)125-56-28-47(88)66(102)31(2)118-56)120-40-15-8-34(9-16-40)68(104)63(94-76(108)58(89-4)33-6-13-41(14-7-33)121-83-74(116-5)70(106)67(103)32(3)119-83)80(112)91-60(36-11-18-49(99)44(85)21-36)77(109)92-61(38)79(111)90-59-35-10-17-48(98)42(20-35)57-43(25-39(97)26-50(57)100)62(82(114)115)93-81(113)64(72)95-78(59)110/h6-26,30-32,46-47,54-56,58-72,74-75,83-84,89,96-107H,27-29,87-88H2,1-5H3,(H,90,111)(H,91,112)(H,92,109)(H,93,113)(H,94,108)(H,95,110)(H,114,115)/t30-,31-,32?,46-,47-,54+,55-,56-,58?,59+,60?,61+,62-,63+,64-,65-,66-,67?,68+,69+,70?,71?,72+,74?,75+,83?,84-/m0/s1 |
| InChI Key | MVUXVKWQCKGLNW-IQJYUAOFSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Acetone |
Reference Reading
1. Helvecardins A and B, novel glycopeptide antibiotics. III. Biological properties
M Takeuchi, T Katayama, M Inukai J Antibiot (Tokyo). 1991 Mar;44(3):278-81. doi: 10.7164/antibiotics.44.278.
Helvecardins (HVCs) A and B were strongly active against aerobic and anaerobic Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), but they were inactive against Gram-negative bacteria and fungi. Though HVC A showed only slightly stronger antimicrobial activity than beta-avoparcin (AVP), its in vivo protective activity against S. aureus infection in mice was greatly superior to AVP.
2. Helvecardins A and B, novel glycopeptide antibiotics. II. Structural elucidation
M Takeuchi, S Takahashi, M Inukai, T Nakamura, T Kinoshita J Antibiot (Tokyo). 1991 Mar;44(3):271-7. doi: 10.7164/antibiotics.44.271.
Helvecardins A and B, which are produced by Pseudonocardia compacta subsp. helvetica, are new members of glycopeptide antibiotics. They contain the same pseudoaglycone as beta-avoparcin and the same compositions of neutral sugar, amino sugar, and amino acid except that 2'-O-methylrhamnose was detected in helvecardins instead of rhamnose in beta-avoparcin, and mannose was not detected in helvecardin B. From these results and 1H NMR and mass spectral analyses, helvecardins A and B were determined beta-avoparcin 2'-O-methylated on rhamnose and demanosylhelvecardin A, respectively.
3. Helvecardins A and B, novel glycopeptide antibiotics. I. Taxonomy, fermentation, isolation and physico-chemical properties
M Takeuchi, R Enokita, T Okazaki, T Kagasaki, M Inukai J Antibiot (Tokyo). 1991 Mar;44(3):263-70. doi: 10.7164/antibiotics.44.263.
A strain of actinomycetes identified as Pseudonocardia compacta subsp. helvetica produced new glycopeptide antibiotics, helvecardins A and B. They were isolated from culture broth mainly by affinity chromatography of D-alanyl-D-alanine and preparative HPLC. The physico-chemical properties of helvecardins A and B showed that they resemble each other. Though helvecardin A was structurally related to beta-avoparcin, it clearly differed in the presence of an O-methyl moiety in its NMR spectrum.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
