Name: Anthramycin
SKU: 4803-27-4

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Basic Information

Molecular Structure:
CAS No.:	4803-27-4
Name:	Anthramycin
Article Data:	2

Formula:	C₁₆H₁₇N₃O₄
Molecular Weight:	315.4
Synonyms:	3-(9,11-dihydroxy-8-methyl-5-oxo-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-2-yl)-acrylamide;(11R,11aS)-5,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo<2,1-c><1,4>benzodiazepin-2-trans-acrylamid;Antramycin;
Density:	1.5g/cm³
Melting Point:	188-194oC
Boiling Point:	679.9°Cat760mmHg
Flash Point:	365°C
Safety:	Deadly poison by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
PSA:	115.89000
LogP:	1.36060

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Chemistry

IUPAC Name: (E)-3-(4,6-dihydroxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl)prop-2-enamide
Molecular Weight: 315.32388 g/mol
Molecular Formula: C₁₆H₁₇N₃O₄
Density: 1.5 g/cm³
Boiling Point: 679.9 °C at 760 mmHg
Flash Point: 365 °C
Index of Refraction: 1.722
Molar Refractivity: 82.95 cm³
Molar Volume: 209.4 cm³
Polarizability: 32.88*10^-24cm³
Surface Tension: 85 dyne/cm
Enthalpy of Vaporization: 104.8 kJ/mol
Vapour Pressure: 2.05E-19 mmHg at 25°C
H-Bond Donor: 4
H-Bond Acceptor: 5
Rotatable Bond Count: 2
Tautomer Count: 14
Exact Mass: 315.121906
MonoIsotopic Mass: 315.121906
Topological Polar Surface Area: 116
Heavy Atom Count: 23
Complexity: 574
Canonical SMILES: CC1=C(C2=C(C=C1)C(=O)N3C=C(CC3C(N2)O)C=CC(=O)N)O
Isomeric SMILES: CC1=C(C2=C(C=C1)C(=O)N3C=C(CC3C(N2)O)/C=C/C(=O)N)O
InChI: InChI=1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+
InChIKey: VGQOVCHZGQWAOI-HWKANZROSA-N

Uses

Anthramycin (CAS NO.4803-27-4), an antitumour antibiotic produced by Streptomyces refuineus, belongs to the pyrrolo(1,4)benzodiazepine antibiotic group. Anthramycin (CAS NO.4803-27-4) within this group are potent inhibitors of nucleic acid synthesis because of their ability to form a labile covalent adduct with DNA.

Toxicity Data With Reference

1.	pic-esc 60 ng/plate	CNREA8 Cancer Research. 43 (1983),2819.
2.	dnd-mam:lym 400 µmol/L	BBACAQ Biochimica et Biophysica Acta. 475 (1977),521.
3.	mmo-eug 60 mg/L	NEOLA4 Neoplasma. 19 (1972),579.
4.	dns-hmn:fbr 200 µmol/L	JBCHA3 Journal of Biological Chemistry. 254 (1979),605.
5.	dnd-hmn:fbr 10 µmol/L	JBCHA3 Journal of Biological Chemistry. 254 (1979),605.
6.	ipr-mus LD50:650 µg/kg	TOLED5 Toxicology Letters. 18 (1983),337.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Deadly poison by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.

Specification

Anthramycin (CAS NO.4803-27-4) is also called (11R,11aS,βE)-5,10,11,11a-Tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-acrylamide ; (11R,11aS,βE)-5,10,11,11a-Tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo[2,1-c][1,4]benzodiazepine-2-acrylamide .Anthramycin (CAS NO.4803-27-4) is high toxic. It is flammable. It will produce toxic nitrogen oxide fumes when buring. So the storage environment should be ventilate, low-temperature and dry. Keep Anthramycin (CAS NO.4803-27-4) separate from raw materials of food.