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83314-01-6 molecular structure
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(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 and InChIs

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

Cite this record

CBID:155755 http://www.chembase.cn/molecule-155755.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[21.3.1.13,7.111,15]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[21.3.1.13,7.111,15]nonacos-8-en-12-yl octa-2,4-dienoate
Synonyms
Bryostatin 1
CAS Number
83314-01-6
MDL Number
MFCD00893832
PubChem SID
24891991
162249893
PubChem CID
22524140

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
B7431 external link Add to cart Please log in.
Data Source Data ID
PubChem 22524140 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 10.585157  H Acceptors 12 
H Donor LogD (pH = 5.5) 5.0399866 
LogD (pH = 7.4) 5.039707  Log P 5.0399904 
Molar Refractivity 233.0506 cm3 Polarizability 91.74598 Å3
Polar Surface Area 240.11 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: soluble expand Show data source
ethanol: soluble expand Show data source
Apperance
white solid expand Show data source
RTECS
EH9455000 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥99% expand Show data source
Empirical Formula (Hill Notation)
C47H68O17 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B7431 external link
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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