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- BIRD-PRD_000001: Actinomycin D -

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Basic information

EntryDatabase: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000001
StatusStatus: REF ONLY
NameActinomycin D

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BIRD information

TypePolypeptide / Antibiotic
Details
  • ACTINOMYCIN D IS A BICYCLIC PEPTIDE, A MEMBER OF THE ACTINOMYCIN FAMILY. HERE, ACTINOMYCIN D IS REPRESENTED BY THE SEQUENCE (SEQRES)
  • ACTINOMYCIN D CONSISTS OF TWO PENTAMER RINGS LINKED BY THE CHROMOPHORE (PXZ)
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • 1H-Pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecine, cyclic peptide deriv. (SciFinder)
  • 2-Amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxylic acidbis-[(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] (PDB)
  • 3H-Phenoxazine, actinomycin D deriv. (SciFinder)
  • 3H-Phenoxazine-1,9-dicarboxamide, 2-amino-N,N'-bis(hexadecahydro-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl)-4,6-dimethyl-3-oxo-(7CI) (SciFinder)
  • A-2600 (ChemSpider)
  • ACTINOMYCIN D (PDB, DrugBank)
  • ActD (Beilstein, DrugBank)
  • Actactinomycin A IV (SciFinder)
  • Actinomycin 7 (SciFinder, PubChem)
  • Actinomycin AIV (SciFinder)
  • Actinomycin Aiv (PubChem)
  • Actinomycin C1 (6CI) (SciFinder)
  • Actinomycin D (JP15) (KEGG)
  • Actinomycin I1 (SciFinder)
  • Actinomycin IV (SciFinder, PubChem)
  • Actinomycin X1 (SciFinder)
  • Actinomycindioic D acid, dilactone (SciFinder)
  • Chounghwamycin B (SciFinder, DrugBank)
  • Compound from Streptomyces Parvullus (DrugBank)
  • Cosmegen (SciFinder, DrugBank)
  • Cosmegen (Merck & Co.) (Merck)
  • Cosmegen (TN) (KEGG)
  • D Meractinomycin (PubChem)
  • DACTINOMYCIN (PubChem)
  • Dactinomicina [INN-Spanish] (DrugBank)
  • Dactinomycin (SciFinder, DrugBank, Norine, PubChem)
  • Dactinomycin (USP) (KEGG)
  • Dactinomycin D (SciFinder)
  • Dactinomycine [INN-French] (DrugBank)
  • Dactinomycinum [INN-Latin] (DrugBank)
  • Dilactone actinomycin D acid (SciFinder)
  • Dilactone actinomycindioic D acid (SciFinder)
  • Lyovac (PubChem)
  • Lyovac Cosmegen (DrugBank)
  • Lyovac cosmegen (SciFinder)
  • Meractinomycin (SciFinder, DrugBank)
  • NCI C04682 (SciFinder)
  • NSC 3053 (SciFinder)
  • Oncostatin K (SciFinder, PubChem)
  • Stereoisomer of N,N'-[(2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-diyl)bis[carbonylimino[2-(1-hydroxyethyl)-1-oxo-2,1-ethanediyl]imino[2-(1-methylethyl)-1-oxo-2,1-ethanediyl]-1,2-pyrrolidine diylcarbonyl(methylimino)(1-oxo-2,1-ethanediyl)]]bis[N-methyl-L-valine]di-epsilon-lactone (SciFinder)
  • actinomycin AIV (Merck)
  • actinomycin C1 (Merck, Beilstein)
  • actinomycin D (PubChem)
  • actinomycin D2 (Beilstein)
  • actinomycin I1 (Merck)
  • actinomycin IV (Merck)
  • actinomycin X1 (Merck)
  • actinomycin-[thr-val-pro-sar-meval] (Merck)
  • cosmegen (PubChem)
  • meractinomycin (Merck)
Annotation
  • Function: antineoplastic / Info source: KEGG
  • Function: Nucleic Acid Synthesis Inhibitor / Info source: DrugBank
  • Function: Protein Synthesis Inhibitor / Info source: DrugBank
  • Function: antibiotic / Info source: Norine
  • Function: antitumor / Info source: Norine
  • Function: transcriptional inhibitor / Info source: PubChem
  • Function: Antineoplastic antibiotic that inhibits DNA-primed RNA polymerase by complexing with DNA via deoxyguanosine residues. At higher concentrations, DNA polymerase is inhibited. / Info source: Merck-Calbiochem
  • Research use: Actinomycin D and its fluorescent derivative, 7-aminoactinomycin D (7-AAD), are used as stains in microscopy and flow cytometry applications. The affinity of these stains compounds for GC-rich regions of DNA strands makes them excellent markers for DNA. 7-AAD binds to single stranded DNA; therefore it is a useful tool in determining apoptosis and distinguishing between dead cells and live ones / Info source: http://www.fermentek.co.il/7AAD.htm
  • Mechanism of action: Good evidence exists that this drug bind strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis. / Info source: DrugBank
  • Pharmacology: Generally, the actinomycins exert an inhibitory effect on gram-positive and gram-negative bacteria and on some fungi. However, the toxic properties of the actinomycins (including dactinomycin) in relation to antibacterial activity are such as to preclude their use as antibiotics in the treatment of infectious diseases. Because the actinomycins are cytotoxic, they have an antineoplastic effect which has been demonstrated in experimental animals with various types of tumor implant. This cytotoxic action is the basis for their use in the treatment of certain types of cancer. Dactinomycin is believed to produce its cytotoxic effects by binding DNA and inhibiting RNA synthesis. / Info source: DrugBank
Source
External info
FamilyACTINOMYCIN

Actinomycin D / 8-Fluoro-Actinomycin D / Actinomycin X2 ...Actinomycin D / 8-Fluoro-Actinomycin D / Actinomycin X2 / Actinomycin Z3 / 7-AminoActinomycin / N8-Actinomycin D

Related structures
  • 2,2'-D-bis(O-Methyltyrosinyl)-actinomycin D ethyl acetate hydrate / CCDC: POHMUU / Reference
  • Actinomycin / CCDC: ZZZGQM / Reference
  • Actinomycin / CCDC: ZZZGQM01 / Reference
  • bis(Deoxyguanylyl-(3'-5')-deoxycytidine) actinomycin D hydrate / CCDC: BEJXET / Reference
  • Actinomycin D ethanol solvate hydrate / CCDC: GIDNUC / Reference
  • Actinomycin D bis(deoxyguanosine) dodecahydrate / CCDC: ACTDGU01 / PubMed / Reference
  • Actinomycin D bis(deoxyguanosine) dodecahydrate / CCDC: ACTDGU10 / PubMed / Reference
  • 7-Bromoactinomycin D bis(deoxyguanosine) undecahydrate / CCDC: BRAXGU / PubMed / Reference
  • Actinomycin C3 / CCDC: ZZZIDA / Reference
  • ACTINOMYCIN C3 / CCDC: ZZZIDA01 / Reference
  • Actinomycin C(3) / CCDC: ZZZWAI / Reference
  • Actinomycin C1 -deoxyguanosine complex / CCDC: QQQAWG / Reference
  • Actinomycin B / CCDC: ZZZJGA / Reference
  • Actinomycin X2 ethyl acetate methanol solvate / CCDC: XERQEQ / Reference

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Chemical information

Composition
Formula: C62H86N12O16 / Formula weight: 1255.417
OthersType: peptide-like
History
External linksUniChem / ChemSpider / Wikipedia search / Google search

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Structure visualization

Structure viewerMolecule:
MolmilJmol/JSmol

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Details

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SMILES

ACDLabs 12.01O=C2N1CCCC1C(=O)N(C)CC(=O)N(C)C(C(=O)OC(C)C(C(=O)NC2C(C)C)NC(=O)c3ccc(c4OC5=C(C(=O)C(N)=C(C5=Nc34)C(=O)NC7C(=O)NC(C(=O)N6CCCC6C(=O)N(C)CC(=O)N(C)C(C(=O)OC7C)C(C)C)C(C)C)C)C)C(C)C
CACTVS 3.370CC(C)[CH]1NC(=O)[CH](NC(=O)c2ccc(C)c3OC4=C(C)C(=O)C(=C(C(=O)N[CH]5[CH](C)OC(=O)[CH](C(C)C)N(C)C(=O)CN(C)C(=O)[CH]6CCCN6C(=O)[CH](NC5=O)C(C)C)C4=Nc23)N)[CH](C)OC(=O)[CH](C(C)C)N(C)C(=O)CN(C)C(=O)[CH]7CCCN7C1=O
OpenEye OEToolkits 1.7.6Cc1ccc(c2c1OC3=C(C(=O)C(=C(C3=N2)C(=O)NC4C(OC(=O)C(N(C(=O)CN(C(=O)C5CCCN5C(=O)C(NC4=O)C(C)C)C)C)C(C)C)C)N)C)C(=O)NC6C(OC(=O)C(N(C(=O)CN(C(=O)C7CCCN7C(=O)C(NC6=O)C(C)C)C)C)C(C)C)C

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SMILES CANONICAL

CACTVS 3.370CC(C)[C@H]1NC(=O)[C@@H](NC(=O)c2ccc(C)c3OC4=C(C)C(=O)C(=C(C(=O)N[C@H]5[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]6CCCN6C(=O)[C@H](NC5=O)C(C)C)C4=Nc23)N)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]7CCCN7C1=O
OpenEye OEToolkits 1.7.6Cc1ccc(c2c1OC3=C(C(=O)C(=C(C3=N2)C(=O)N[C@H]4[C@H](OC(=O)[C@@H](N(C(=O)CN(C(=O)[C@@H]5CCCN5C(=O)[C@H](NC4=O)C(C)C)C)C)C(C)C)C)N)C)C(=O)N[C@H]6[C@H](OC(=O)[C@@H](N(C(=O)CN(C(=O)[C@@H]7CCCN7C(=O)[C@H](NC6=O)C(C)C)C)C)C(C)C)C

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InChI

InChI 1.03InChI=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

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InChIKey

InChI 1.03RJURFGZVJUQBHK-VSWUTOEJSA-N

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SYSTEMATIC NAME

ACDLabs 12.012-amino-4,6-dimethyl-3-oxo-N~9~-[(6R,9S,10S,13S,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-di(propan-2-yl)hexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-N~1~-[(6S,9S,10R,13R,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-di(propan-2-yl)hexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-3H-phenoxazine-1,9-dicarboxamide
OpenEye OEToolkits 1.7.62-azanyl-4,6-dimethyl-3-oxidanylidene-N1,N9-bis[(3R,6S,7R,10S,16S)-7,11,14-trimethyl-2,5,9,12,15-pentakis(oxidanylidene)-3,10-di(propan-2-yl)-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]phenoxazine-1,9-dicarboxamide

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