(1S,3S,7R,11S,12S,15S,17R,21R,23R,25S)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl octa-2,4-dienoate

• ChemBase ID: 155755
• Molecular Formular: C47H68O17
• Molecular Mass: 905.03262
• Monoisotopic Mass: 904.44565072
• SMILES: CCC/C=C/C=C/C(=O)O[C@@H]1[C@]2(O[C@@H](C/C/1=C\C(=O)OC)C[C@@H](OC(=O)C[C@@H](C[C@H]1O[C@](C([C@H](C1)OC(=O)C)(C)C)(C[C@H]1O[C@@H](/C=C\C2(C)C)C/C(=C\C(=O)OC)/C1)O)O)[C@H](O)C)O
• Canonical SMILES: CCC/C=C/C=C/C(=O)O[C@H]1/C(=C/C(=O)OC)/C[C@@H]2O[C@@]1(O)C(C)(C)/C=C\[C@@H]1O[C@@H](C/C(=C/C(=O)OC)/C1)C[C@]1(O)O[C@H](C[C@H](CC(=O)O[C@H](C2)[C@H](O)C)O)C[C@@H](C1(C)C)OC(=O)C
• InChI: InChI=1S/C47H68O17/c1-10-11-12-13-14-15-39(51)62-43-31(22-41(53)58-9)21-34-25-37(28(2)48)61-42(54)24-32(50)23-35-26-38(59-29(3)49)45(6,7)46(55,63-35)27-36-19-30(20-40(52)57-8)18-33(60-36)16-17-44(4,5)47(43,56)64-34/h12-17,20,22,28,32-38,43,48,50,55-56H,10-11,18-19,21,23-27H2,1-9H3/t28-,32-,33+,34+,35-,36+,37-,38+,43+,46+,47-/m1/s1
• InChIKey: MJQUEDHRCUIRLF-KNUVDIFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,7R,11S,12S,15S,17R,21R,23R,25S)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1^3,^7.1^1^1,^1^5]nonacos-8-en-12-yl octa-2,4-dienoate
• IUPAC Traditional name: (1S,3S,7R,11S,12S,15S,17R,21R,23R,25S)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1^3,^7.1^1^1,^1^5]nonacos-8-en-12-yl octa-2,4-dienoate
• Synonyms: Bryostatin 1

Database IDs

• CAS Number: 83314-01-6
• MDL Number: MFCD00893832
• PubChem SID: 24891991; 162249893
• PubChem CID: 22524140

CALCULATED PROPERTIES

• Acid pKa: 10.585157
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 5.0399866
• LogD (pH = 7.4): 5.039707
• Log P: 5.0399904
• Molar Refractivity: 233.0506 cm^3
• Polarizability: 91.74598 Å^3
• Polar Surface Area: 240.11 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble
• Apperance: white solid

Safety Information

• RTECS: EH9455000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99%
• Empirical Formula (Hill Notation): C47H68O17

DETAILS

Sigma Aldrich - B7431

Biochem/physiol Actions
Macrolactone isolated from the marine bryozoan Bugula neritina that initially activates and subsequently down-regulates protein kinase C (PKC). More potent than phorbol myristate acetate for translocating PKCδ and ε.
Other Notes
Binds to glass and plastic in aqueous solutions