Hibarimicin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00955 |
| CAS | |
| Molecular Weight | 1683.74 |
| Molecular Formula | C83H110O36 |
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Description
Hibarimicin C is a tyrosine kinase inhibitor produced by Microbispora rosea subsp. hibaria. It selectively inhibits the activity of src tyrosine kinase without affecting protein kinase A and C. It also has moderate anti-Gram-positive bacteria activity with a MIC of 0.8-12.56 μg/mL.
Specification
| IUPAC Name | 15-[9-[(2S,5S,6R)-5-[(2R,5S,6S)-5-acetyl-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-7-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1,8,10,10a,12-pentahydroxy-3,4-dimethoxy-11-oxo-10-propyl-6a,7,8,9-tetrahydro-6H-tetracen-2-yl]-7-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6,9,12,19-tetrahydroxy-5-[(2S,5S,6R)-5-[(2S,5S,6R)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-16-methoxy-4-propyl-3-oxapentacyclo[9.8.0.02,8.04,9.013,18]nonadeca-1(11),12,15,18-tetraene-10,14,17-trione |
| Canonical SMILES | CCCC1(C(C(C(C2C1(C(=O)C3=C(C4=C(C=C3C2)C(=C(C(=C4O)C5=C(C(=O)C6=C(C7=C(C(=C6C5=O)O)C(=O)C8(C9C7OC8(C(C(C9OC1CC(C(C(O1)C)O)O)O)OC1CCC(C(O1)C)OC1CCC(C(O1)C)O)CCC)O)O)OC)OC)OC)O)O)OC1CC(C(C(O1)C)O)O)O)OC1CCC(C(O1)C)OC1CCC(C(O1)C)(C(=O)C)O)O |
| InChI | InChI=1S/C83H110O36/c1-13-22-80(101)77(117-45-19-16-43(31(5)108-45)114-47-21-24-79(100,34(8)84)35(9)112-47)67(96)70(115-48-27-40(86)59(88)32(6)110-48)38-26-36-25-37-51(61(90)50(36)75(98)82(38,80)102)62(91)55(73(106-12)69(37)104-10)54-63(92)52-53(66(95)72(54)105-11)64(93)56-57(65(52)94)76(99)83(103)58-71(56)119-81(83,23-14-2)78(68(97)74(58)116-49-28-41(87)60(89)33(7)111-49)118-46-20-17-42(30(4)109-46)113-44-18-15-39(85)29(3)107-44/h25,29-33,35,38-49,58-60,67-68,70-71,74,77-78,85-91,93-94,96-97,100-103H,13-24,26-28H2,1-12H3/t29-,30-,31-,32+,33+,35+,38?,39+,40-,41-,42+,43+,44+,45+,46+,47+,48+,49+,58?,59+,60+,67?,68?,70?,71?,74?,77?,78?,79-,80?,81?,82?,83?/m1/s1 |
| InChI Key | WYVNHQPOEAJLTF-WBORRCEUSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >200°C |
Reference Reading
1. Signal transduction inhibitors, hibarimicins A, B, C, D and G produced by Microbispora. II. Structural studies
H Hori, Y Igarashi, T Kajiura, T Furumai, K Higashi, T Ishiyama, M Uramota, Y Uehara, T Oki J Antibiot (Tokyo). 1998 Apr;51(4):402-17. doi: 10.7164/antibiotics.51.402.
The structure of hibarimicins A, B, C, D and G which are inhibitors for tyrosine specific protein kinase are determined using spectroscopic techniques. Hibarimicins described in this report consist of a common aglycon and six deoxyhexoses. The aglycon contains a highly oxidized naphtylnaphthoquinone as a chromophore. Among them, hibarimicin B was identical with angelmicin B.
2. Signal transduction inhibitors, hibarimicins, A, B, C, D and G produced by Microbispora. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties
T Kajiura, T Furumai, Y Igarashi, H Hori, K Higashi, T Ishiyama, M Uramoto, Y Uehara, T Oki J Antibiot (Tokyo). 1998 Apr;51(4):394-401. doi: 10.7164/antibiotics.51.394.
Strain TP-AO121 which produces a complex of novel tyrosine kinase inhibitors designated hibarimicins A, B, C, D and G was considered to be a new subspecies of Microbispora rosea, and the name, Microbispora rosea subsp. hibaria, was proposed. Hibarimicins A, B, C and D specifically inhibited the src tyrosine kinase activity without affecting protein kinase A or protein kinase C. They also showed in vitro anti-Gram-positive bacterial and antitumor activities. The molecular formulae of hibarimicins A, B, C, D and G were assigned to be C85H112O37, C85H112O37, C83H110O36, C85H112O38, and C85H112O39 respectively.
3. Effects of hibarimicins and hibarimicin-related compounds produced by Microbispora on v-Src kinase activity and growth and differentiation of human myeloid leukemia HL-60 cells
Sung Ig Cho, Hidesuke Fukazawa, Yoshio Honma, Takayuki Kajiura, Hiroshi Hori, Yasuhiro Igarashi, Tamotsu Furumai, Toshikazu Oki, Yoshimasa Uehara J Antibiot (Tokyo). 2002 Mar;55(3):270-8. doi: 10.7164/antibiotics.55.270.
We studied the effects of hibarimicins and hibarimicin-related compounds produced by Microbispora rosea subsp. hibaria [glycosides (hibarimicins A, B, C, D, E, G, H and I) and aglycon (hibarimicinone)] or compounds produced by its mutants [glycosides (HMP-P4 and -Y6), aglycons (HMP-P1 and -Y1) and shunt products (HMP-M1, M2, M3 and -M4)] on v-Src tyrosine kinase and growth and differentiation of human myeloid leukemia HL-60 cells. Among them, hibarimicin B was a strong and the most selective v-Src kinase inhibitor with differentiation inducing activity of HL-60 cells. Hibarimicin E similarly induced HL-60 cell differentiation but had no v-Src kinase inhibitory activity. Hibarimicinone was the most potent v-Src kinase inhibitor, although less selective, and did not induce differentiation of HL-60 cells. Hibarimicin B competitively inhibited ATP binding to the v-Src kinase, but hibarimicinone showed noncompetitive inhibition. These two compounds, however, showed similar mixed types of inhibition against a Src substrate binding to the v-Src kinase. Altogether, these results suggest that signaling molecules other than Src might be more important in the differentiation induction of HL-60 cells.
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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 ╳
