Hypothemycin

Modify Date: 2024-01-02 10:50:22

Hypothemycin Structure
Hypothemycin structure
 Common Name Hypothemycin
CAS Number 76958-67-3 Molecular Weight 378.37300
Density 1.343g/cm3 Boiling Point 673.1ºC at 760 mmHg
Molecular Formula C19H22O8 Melting Point 170-172℃
MSDS Chinese USA Flash Point 242.7ºC

 Use of Hypothemycin


Hypothemycin, a fungal polyketide, is a multikinase inhibitor with Kis of 10/70 nM, 17/38 nM, 90 nM, 900 nM/1.5 μM, and 8.4/2.4 μM for VEGFR2/VEGFR1, MEK1/MEK2, FLT-3, PDGFRβ/PDGFRα, and ERK1/ERK2, respectively[1][2].

 Names

Name hypothemycin
Synonym More Synonyms

 Hypothemycin Biological Activity

Description Hypothemycin, a fungal polyketide, is a multikinase inhibitor with Kis of 10/70 nM, 17/38 nM, 90 nM, 900 nM/1.5 μM, and 8.4/2.4 μM for VEGFR2/VEGFR1, MEK1/MEK2, FLT-3, PDGFRβ/PDGFRα, and ERK1/ERK2, respectively[1][2].
Related Catalog
Target

VEGFR2:10 nM (Ki)

VEGFR1:70 nM (Ki)

MEK1:17 nM (Ki)

MEK2:38 nM (Ki)

FLT-3:90 nM (Ki)

PDGFRα:1.5 μM (Ki)

PDGFRβ:900 nM (Ki)

ERK1:8.4 μM (Ki)

ERK2:2.4 μM (Ki)

In Vitro Hypothemycin inhibits eosinophilic EOL1 cell carrying mutations in FIP1L1-PDGFRα, acute myeloid leukemia MV-4-11 cell carrying mutations in FLT3-ITD, melanoma COLO829 cell carrying mutations in BRAF V600E, HUVEC cell carrying mutations in VEGFR, mastocytoma P815 cell carrying mutations in c-KIT D814Y, NSCLC A459 cell carrying mutations in KRAS, and ovarian SKOV-3 cell carrying mutations in HER2 with IC50s of 0.4 nM, 6 nM, 50 nM, 70 nM, 370 nM, 6.0 μM, and 7.0 μM, respectively[2].
In Vivo Hypothemycin (10 mg/kg) kills T. brucei in infected mice, completely curing the infection in one third of animals, although high doses of Hypothemycin (>10 mg/kg) leads to side effects[1]. Animal Model: Adult female Balb/c mice (weighing 18–22 g) infected with T. brucei[1] Dosage: 10 mg/kg Administration: Administered once daily via intraperitoneal injection for 7 days. Result: Showed a dose-dependent reduction in parasitemia in infected mice. Prolonged survival of infected mice over 30 days, with a cure rate of 33%.
References

[1]. Schirmer A, et al. Targeted covalent inactivation of protein kinases by resorcylic acid lactone polyketides. Proc Natl Acad Sci U S A. 2006 Mar 14;103(11):4234-9.

[2]. Nishino M, et al. Hypothemycin, a fungal natural product, identifies therapeutic targets in Trypanosoma brucei. Elife. 2013 Jul 9;2:e00712.

 Chemical & Physical Properties

Density 1.343g/cm3
Boiling Point 673.1ºC at 760 mmHg
Melting Point 170-172℃
Molecular Formula C19H22O8
Molecular Weight 378.37300
Flash Point 242.7ºC
Exact Mass 378.13100
PSA 125.82000
LogP 1.02690
Index of Refraction 1.573
Storage condition 20°C

 Safety Information

Hazard Codes Xn
Risk Phrases R22

 Synthetic Route

5Z-7-Oxozeaenol structure

5Z-7-Oxozeaenol

CAS#:253863-19-3

~16%

Hypothemycin Structure

Hypothemycin

CAS#:76958-67-3

Literature: Selles, Patrice; Lett, Robert Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4627 - 4631
(3aR,5Z,8S,15E)-4,11-dihydroxy-13-methoxy-2,2,8-trimethyl-3a,4,7,8,17,17a-hexahydro-10H-benzo[c][1,3]dioxolo[4,5-h][1]oxacyclotetradecin-10-one structure

(3aR,5Z,8S,15E)...

CAS#:460358-69-4

~%

Hypothemycin Structure

Hypothemycin

CAS#:76958-67-3

Literature: Selles, Patrice; Lett, Robert Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4627 - 4631
N/A structure

N/A

CAS#:460358-62-7

~%

Hypothemycin Structure

Hypothemycin

CAS#:76958-67-3

Literature: Selles, Patrice; Lett, Robert Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4627 - 4631
(2S,Z)-6-((4S)-2,2-dimethyl-5-(prop-2-yn-1-yl)-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl 2-bromo-6-hydroxy-4-methoxybenzoate structure

(2S,Z)-6-((4S)-...

CAS#:460348-31-6

~%

Hypothemycin Structure

Hypothemycin

CAS#:76958-67-3

Literature: Selles, Patrice; Lett, Robert Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4627 - 4631
N/A structure

N/A

CAS#:460348-38-3

~%

Hypothemycin Structure

Hypothemycin

CAS#:76958-67-3

Literature: Selles, Patrice; Lett, Robert Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4627 - 4631
fr264744 structure

fr264744

CAS#:66018-39-1

~%

Hypothemycin Structure

Hypothemycin

CAS#:76958-67-3

Literature: Selles, Patrice; Lett, Robert Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4627 - 4631
(3aR,4R,5Z,8S,15E)-4,11-dihydroxy-13-methoxy-2,2,8-trimethyl-3a,4,7,8,17,17a-hexahydro-10H-benzo[c][1,3]dioxolo[4,5-h][1]oxacyclotetradecin-10-one structure

(3aR,4R,5Z,8S,1...

CAS#:460358-77-4

~%

Hypothemycin Structure

Hypothemycin

CAS#:76958-67-3

Literature: Selles, Patrice; Lett, Robert Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4627 - 4631

 Precursor & DownStream

Precursor  2

DownStream  0

 Synonyms

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione
MFCD08457932
Hypothemicin
(1aR,3S,4S,6Z,9S,15bR)-1a,2,4,5,11,8,9,15b-Octahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11-dione
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