1-N,9-N-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-bis(propan-2-yl)-hexadecahydro-1H-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide

• ChemBase ID: 130507
• Molecular Formular: C62H86N12O16
• Molecular Mass: 1255.41704
• Monoisotopic Mass: 1254.62847473
• SMILES: CC(C)[C@H]1NC(=O)[C@@H](NC(=O)c2ccc(C)c3oc4c(C)c(=O)c(N)c(c4nc23)C(=O)N[C@H]2C(=O)N[C@H](C(=O)N3CCC[C@H]3C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]2C)C(C)C)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C1=O
• Canonical SMILES: O=C1N[C@@H](C(C)C)C(=O)N2CCC[C@H]2C(=O)N(C)CC(=O)N([C@H](C(=O)O[C@@H]([C@H]1NC(=O)c1c2nc3c(ccc(c3oc2c(c(=O)c1N)C)C)C(=O)N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C(=O)[C@H]2N(C(=O)[C@H](NC1=O)C(C)C)CCC2)C)C)C(C)C)C
• InChI: InChI=1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1
• InChIKey: RJURFGZVJUQBHK-IIXSONLDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-N,9-N-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-bis(propan-2-yl)-hexadecahydro-1H-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide
• IUPAC Traditional name: actinomycin D
• Brand Name: Cosmegen
• Synonyms: 2-Amino- 4,6-dimethyl- 3-oxo- 3H-phenoxazine- 1,9-dicarboxylic acid bis- [(5,12-diisopropyl- 9,13,16-trimethyl- 4,7,11,14,17-pentaoxo- hexadecahydro- 10-oxa- 3a,6,13,16-tetraaza- cyclopentacyclohexadecen- 8-yl)- amide]; Actinomycin; Actinomycin C1; Actinomycin IV; Dactinomycin; Actinomycin D; 放线菌素 C1; 放线菌素 IV; 更生霉素; 放线菌素 D

Database IDs

• CAS Number: 50-76-0
• EC Number: 200-063-6
• MDL Number: MFCD00005033
• Beilstein Number: 605235
• PubChem SID: 162224786
• PubChem CID: 457193; 2019
• CHEBI ID: 27666
• ATC CODE: L01DA01
• CHEMBL: 1554
• Chemspider ID: 10482167
• DrugBank ID: DB00970
• KEGG ID: C06770
• Unique Ingredient Identifier: 1CC1JFE158
• Wikipedia Title: Actinomycin
• Medline Plus: a682224

CALCULATED PROPERTIES

• Acid pKa: 10.516916
• H Acceptors: 16
• H Donor: 5
• LogD (pH = 5.5): -0.09688717
• LogD (pH = 7.4): -0.09717637
• Log P: -0.096882455
• Molar Refractivity: 326.1716 cm^3
• Polarizability: 124.87235 Å^3
• Polar Surface Area: 355.54 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble10 mg/mL, clear, orange to red
• Apperance: red, powder
• Melting Point: 251-253

Safety Information

• RTECS: AU1575000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 22-28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: IV
• Half Life: 36 hours
• Protein Bound: 5%
• Legal Status: Rx-only
• Pregnancy Category: D

Product Information

• Purity: ≥98.0% (HPLC)
• Biological Source: from Streptomyces sp.
• Empirical Formula (Hill Notation): C62H86N12O16

DETAILS

Sigma Aldrich - 01817

Biochem/physiol Actions
An antineoplastic antibiotic that inhibits cell proliferation by forming a stable complex with DNA and blocking the movement of RNA polymerase which interferes with DNA-dependent RNA synthesis. Induces apoptosis. Potent antitumor agent. For cell culture applications, actinomycin D is used as a selection agent and is used in banding techniques to differentiate between different regions of chromosomes.
Other Notes
Inhibits DNA-dependent RNA synthesis. DNA-binding drug1,2,3