(3S,6S,9S,16S,21aR)-3-[(2S)-butan-2-yl]-5,8,9-trimethyl-16-(prop-2-en-1-yl)-6-(propan-2-yl)-icosahydropyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-1,4,7,10,14,17-hexone

• ChemBase ID: 133996
• Molecular Formular: C29H47N5O7
• Molecular Mass: 577.71278
• Monoisotopic Mass: 577.34754887
• SMILES: CC[C@H](C)[C@H]1C(=O)N([C@H](C(=O)N([C@H](C(=O)NCCC(=O)O[C@H](C(=O)N2CCC[C@@H]2C(=O)N1)CC=C)C)C)C(C)C)C
• Canonical SMILES: C=CC[C@@H]1OC(=O)CCNC(=O)[C@H](C)N(C)C(=O)[C@@H](N(C(=O)[C@@H](NC(=O)[C@@H]2N(C1=O)CCC2)[C@H](CC)C)C)C(C)C
• InChI: InChI=1S/C29H47N5O7/c1-9-12-21-27(38)34-16-11-13-20(34)26(37)31-23(18(5)10-2)28(39)33(8)24(17(3)4)29(40)32(7)19(6)25(36)30-15-14-22(35)41-21/h9,17-21,23-24H,1,10-16H2,2-8H3,(H,30,36)(H,31,37)/t18-,19-,20+,21-,23-,24-/m0/s1
• InChIKey: XIYSEKITPHTMJT-UTJJDKHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,16S,21aR)-3-[(2S)-butan-2-yl]-5,8,9-trimethyl-16-(prop-2-en-1-yl)-6-(propan-2-yl)-icosahydropyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-1,4,7,10,14,17-hexone
• IUPAC Traditional name: (3S,6S,9S,16S,21aR)-3-[(2S)-butan-2-yl]-6-isopropyl-5,8,9-trimethyl-16-(prop-2-en-1-yl)-dodecahydropyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-1,4,7,10,14,17-hexone
• Synonyms: Destruxin A from Metarrhizium anisopliae

Database IDs

• CAS Number: 6686-70-0
• MDL Number: MFCD01736100
• PubChem SID: 162228273
• PubChem CID: 71308749

CALCULATED PROPERTIES

• Acid pKa: 12.515317
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.780975
• LogD (pH = 7.4): 0.78097206
• Log P: 0.780975
• Molar Refractivity: 151.2839 cm^3
• Polarizability: 59.355305 Å^3
• Polar Surface Area: 145.43 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: HH1500000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-48
• Safety Statements: 26-36-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - D4921

Biochem/physiol Actions
Destruxin A is a cyclic hexadepsipeptide produced by fungus causing paralysis and death in insects. May suppress the insect immune response.1 Possesses an inhibitory activity on leukemic cell proliferation, decreasing the number of cells in G2/M phase.2 It is virustatic against arboviruses.3
Quality
Balance is other destruxins