9-N-[(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]-1-N-[(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]-2,7-diamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide

• ChemBase ID: 133026
• Molecular Formular: C62H87N13O16
• Molecular Mass: 1270.43168
• Monoisotopic Mass: 1269.63937377
• SMILES: Cc1c(cc(c2c1oc1c(c(=O)c(c(c1n2)C(=O)N[C@H]1[C@H](OC(=O)C(N(C(=O)CN(C(=O)[C@@H]2CCCN2C(=O)[C@H](NC1=O)C(C)C)C)C)C(C)C)C)N)C)C(=O)N[C@H]1[C@H](OC(=O)[C@@H](N(C(=O)CN(C(=O)[C@@H]2CCCN2C(=O)[C@H](NC1=O)C(C)C)C)C)C(C)C)C)N
• Canonical SMILES: O=C1N[C@H](C(C)C)C(=O)N2CCC[C@H]2C(=O)N(C)CC(=O)N(C(C(=O)O[C@@H]([C@@H]1NC(=O)c1c2nc3c(cc(c(c3oc2c(c(=O)c1N)C)C)N)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/C62H87N13O16/c1-26(2)42-59(85)74-21-17-19-36(74)57(83)70(13)24-38(76)72(15)48(28(5)6)61(87)89-32(11)44(55(81)66-42)68-53(79)34-23-35(63)30(9)51-46(34)65-47-40(41(64)50(78)31(10)52(47)91-51)54(80)69-45-33(12)90-62(88)49(29(7)8)73(16)39(77)25-71(14)58(84)37-20-18-22-75(37)60(86)43(27(3)4)67-56(45)82/h23,26-29,32-33,36-37,42-45,48-49H,17-22,24-25,63-64H2,1-16H3,(H,66,81)(H,67,82)(H,68,79)(H,69,80)/t32-,33-,36+,37+,42-,43-,44+,45+,48+,49?/m1/s1
• InChIKey: YXHLJMWYDTXDHS-SGILFZQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-N-[(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]-1-N-[(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]-2,7-diamino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide
• IUPAC Traditional name: 9-N-[(6S,9R,10S,13R,18aS)-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-decahydropyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-1-N-[(9R,10S,13R,18aS)-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-decahydropyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2,7-diamino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboxamide
• Synonyms: 7-AAD; 7-Aminoactinomycin D

Database IDs

• CAS Number: 7240-37-1
• MDL Number: MFCD00077295
• Beilstein Number: 5915844
• PubChem SID: 24891445; 162227303
• PubChem CID: 16218991

CALCULATED PROPERTIES

• Acid pKa: 10.541236
• H Acceptors: 17
• H Donor: 6
• LogD (pH = 5.5): -0.9260221
• LogD (pH = 7.4): -0.926089
• Log P: -0.9258084
• Molar Refractivity: 330.872 cm^3
• Polarizability: 126.034424 Å^3
• Polar Surface Area: 381.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble1 mg/mL, clear, red
• Apperance: red to dark purple powder

Safety Information

• RTECS: AU1579000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28-36/37/38
• Safety Statements: 26-28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H315-H319-H330-H335
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P264-P280-P284-P302 + P350-P305 + P351 + P338
• 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

Product Information

• Purity: ~97% (HPLC); ≥97.0% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C62H87N13O16

DETAILS

Sigma Aldrich - A9400

Application
Fluorescent DNA stain

Sigma Aldrich - 06648

Other Notes
Fluorescent derivative of actinomycin D. Binding to single-stranded DNA1