Hibarimicin G
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00958 |
| CAS | |
| Molecular Weight | 1757.77 |
| Molecular Formula | C85H112O39 |
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Description
Hibarimicin G is a tyrosine kinase inhibitor produced by Microbispora rosea subsp. hibaria.
Specification
| IUPAC Name | 5-[(2S,5S,6R)-5-[(2R,4R,5S,6S)-5-acetyl-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-15-[9-[(2S,5S,6R)-5-[(2R,4R,5S,6S)-5-acetyl-4,5-dihydroxy-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-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)OC1CC(C(C(O1)C)(C(=O)C)O)O)CCC)O)O)OC)OC)OC)O)O)OC1CC(C(C(O1)C)O)O)O)OC1CCC(C(O1)C)OC1CC(C(C(O1)C)(C(=O)C)O)O)O |
| InChI | InChI=1S/C85H112O39/c1-14-20-80(104)78(122-45-18-16-41(28(3)112-45)118-49-26-43(90)82(105,32(7)86)34(9)116-49)68(100)71(120-47-24-39(88)60(92)30(5)114-47)38-23-36-22-37-52(62(94)51(36)76(102)84(38,80)107)63(95)56(74(111-13)70(37)109-11)55-64(96)53-54(67(99)73(55)110-12)65(97)57-58(66(53)98)77(103)85(108)59-72(57)124-81(85,21-15-2)79(69(101)75(59)121-48-25-40(89)61(93)31(6)115-48)123-46-19-17-42(29(4)113-46)119-50-27-44(91)83(106,33(8)87)35(10)117-50/h22,28-31,34-35,38-50,59-61,68-69,71-72,75,78-79,88-95,97-98,100-101,104-108H,14-21,23-27H2,1-13H3/t28-,29-,30+,31+,34+,35+,38?,39-,40-,41+,42+,43-,44-,45+,46+,47+,48+,49+,50+,59?,60+,61+,68?,69?,71?,72?,75?,78?,79?,80?,81?,82-,83-,84?,85?/m1/s1 |
| InChI Key | KDLAXKWCMPFSGH-FFPHRYDESA-N |
Properties
| Appearance | Red Powder |
| Melting Point | >200°C |
Reference Reading
1. 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.
2. 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.
3. 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.
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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 ╳
