Helvecardin A
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| Category | Antibiotics |
| Catalog number | BBF-01334 |
| CAS | 119979-33-8 |
| Molecular Weight | 1957.74 |
| Molecular Formula | C90H103Cl2N9O36 |
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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 | Avoparcin alpha, 49-chloro-2C-O-methyl-; 49-Chloro-2'''''-O-methylavoparcin α |
| 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]-32,35,37-trihydroxy-20,23,26,42,44-pentaoxo-18-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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)OC1C(C(C(C(O1)CO)O)O)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/C90H103Cl2N9O36/c1-31-67(108)47(93)27-57(126-31)134-77-38-12-19-52(46(92)22-38)131-54-24-39-23-53(78(54)137-90-80(74(115)71(112)56(30-103)133-90)135-58-28-48(94)68(109)32(2)127-58)129-41-15-8-35(9-16-41)76(136-88-75(116)72(113)70(111)55(29-102)132-88)65(100-81(117)60(95-4)34-6-13-42(14-7-34)130-89-79(125-5)73(114)69(110)33(3)128-89)85(121)97-62(37-11-18-50(106)45(91)21-37)82(118)98-63(39)84(120)96-61-36-10-17-49(105)43(20-36)59-44(25-40(104)26-51(59)107)64(87(123)124)99-86(122)66(77)101-83(61)119/h6-26,31-33,47-48,55-58,60-77,79-80,88-90,95,102-116H,27-30,93-94H2,1-5H3,(H,96,120)(H,97,121)(H,98,118)(H,99,122)(H,100,117)(H,101,119)(H,123,124)/t31-,32-,33?,47-,48-,55?,56+,57-,58-,60?,61+,62?,63+,64-,65+,66-,67-,68-,69?,70?,71+,72?,73?,74?,75?,76+,77+,79?,80+,88?,89?,90-/m0/s1 |
| InChI Key | ZVRVZYXIMVTOQM-ZUQUPIACSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Acetone |
Reference Reading
1. 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.
2. 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.
3. 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.
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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 ╳
