Basic information
- CAS
512-64-1- Standard SMILES
CSC1SC[C@H]2C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)c3cnc4ccccc4n3)C(=O)N[C@H](C)C(=O)N(C)[C@@H]1C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)c1cnc3ccccc3n1)C(=O)N[C@H](C)C(=O)N2C- InChIKey
AUJXLBOHYWTPFV-CVLRASHMSA-N- Molecular formula
- C51H64N12O12S2
- Average molar mass
- 1,101.3 g/mol
- Monoisotopic mass
- 1,100.42080787
Overview
S-426-S (Lepetit) has been reported in Streptomyces echinatus with data available.
Names & identifiers
- Preferred name
- S-426-S (Lepetit)
- IUPAC
- N-[(1R,4R,7R,11S,14R,17R,20R,24S)-2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-7-yl]quinoxaline-2-carboxamide
- English name
- QUINOMYCIN A
- Molecular formula
- C51H64N12O12S2
- Molecular weight
- 1101.26
Names & synonyms
S-426-S (Lepetit)N-[(1R,4R,7R,11S,14R,17R,20R,24S)-2,4,12,15,17,25-Hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-7-yl]quinoxaline-2-carboxamideN-[(11S,24S,1R,4R,7R,14R,17R,20R)-2,5,12,15,18,25-hexaaza-11,24-bis(methylethyl)-2,4,12,15,17,25-hexamethyl-27-methylthio-9,22-dioxa-3,6,10,13,16,19,23,26-octaoxo-20-(quinoxalin-2-ylcarbonylamino)-28-thiabicyclo[12.12.3]nonacos-7-yl]quinoxalin-2-ylcarboxamideN-[(1R,4R,7R,11S,14R,17R,20R,24S)-11,24-diisopropyl-2,4,12,15,17,25-hexamethyl-29-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-7-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-20-yl]quinoxaline-2-carboxamideECHINOMYCINSK-302Bnsc526417NSC 13502echinomycinaQUINOMYCIN AEchinomycin >97%Antibiotic A 654I
Show more names
Echinomycin (NSC-13502)Echinomycin, HIF-1alpha inhibitor
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 352 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 7
- Heavy atoms
- 77
- Formal charge
- 0
- Complexity
- 2,200
Physicochemical properties
- Melting point
- 217 · 217-218℃
- alpha
- 20 · D20 -310° (c = 0.86 in chloroform)
- Boiling point
- 1427.2 · 1427.2±65.0 °C(Predicted)
- Density
- 1.0964 · 1.0964 (rough estimate)
- refractive index
- 1.67 · 1.6700 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO (up to 5 mg/ml)
- form
- White solid
- pka
- 9.38 · 9.38±0.70(Predicted)
- color
- white to beige
- Merck
- 13 · 13,3531
- Stability
- 1 year · Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months
- InChIKey
- AUJXLBOHYWTPFV-UHFFFAOYSA-N
- SMILES
- S1C(C2N(C(=O)C(NC(=O)C(COC(=O)C(N(C(=O)C(N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c5nc6c(nc5)cccc6)C)C)C1)C)C(C)C)NC(=O)c3nc4c(nc3)cccc4)C)C)SC
- EWG's Food Scores
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- wgk
- 3
- rtecs
- JW5250000
- ridadr
- UN 3462 6.1/PG 2
- hs_code
- 2941900000
- risk_code
- 46-23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T
- safety_code
- 53-36/37/39-45
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301+H311+H331-H361
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralRepr. 2
- Precautionary statements
- P201-P202-P280-P301+P310-P302+P352+P312-P304+P340+P311
Chemistry & industry
Applications
DescriptionHypoxia-inducible factor-1 (HIF-1) is a transcription factor that controls genes involved in glycolysis, angiogenesis, migration, and invasion. Echinomycin is a cell-permeable inhibitor of HIF-1-mediated gene transcription. It acts by intercalating into DNA in a sequence-specific manner, blocking the binding of either HIF-1α or HIF-1β to the hypoxia-responsive element. Echinomycin reversibly inhibits hypoxia-induced HIF-1 transcription activity in U215 cells with an EC50 value of 1.2 nM. It inhibits hypoxia-induced expression of vascular endothelial growth factor, blocking angiogenesis and altering excitatory synaptic transmission in hippocampal neurons. Echinomycin also impairs expression of survivin, enhancing the sensitivity of multiple myeloma cells to melphalan.
UsesQuiniomycin A is a cyclic depsipeptide metabolite. Quinomycin A has broad activity against bacteria, fungi and viruses, and has found application as an antitumour agent. Quinomycin A acts by bifunctional intercalation of nucleic acids. Recent research has shown quinomycin A to be an extremely potent inhibitor of hypoxia-inducible factor-1 (HIF-1). This transcription factor plays an essential role in tumour progression and metastasis.
UsesQuinomycin A is a cyclic depsipeptide metabolite. Quinomycin A has broad activity against bacteria, fungi and viruses, and has found application as an antitumor agent. Quinomycin A acts by bifunctional intercalation of nucleic acids. Recent research has shown quinomycin A to be an extremely potent inhibitor of hypoxia-inducible factor-1 (HIF-1). This transcription factor plays an essential role in tumor progression and metastasis.
UsesEchinomycin has been used for inhibition of hypoxia-inducible factor 1.
Suppliers44 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
Related reactions
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Compound notes
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