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60857-08-1 molecular structure
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(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-13-yl acetate

ChemBase ID: 177076
Molecular Formular: C22H30O6
Molecular Mass: 390.47
Monoisotopic Mass: 390.20423868
SMILES and InChIs

SMILES:
[C@@H]12[C@](CC(=C[C@@H]3[C@@]1([C@@H](C[C@@]1([C@H]3C1(C)C)OC(=O)C)C)O)CO)(C(=O)C(=C2)C)O
Canonical SMILES:
OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)C)C[C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C
InChI:
InChI=1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17?,20-,21+,22-/m1/s1
InChIKey:
BOJKFRKNLSCGHY-KUHYLXMHSA-N

Cite this record

CBID:177076 http://www.chembase.cn/molecule-177076.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-13-yl acetate
IUPAC Traditional name
prostratin
Synonyms
(1aR,1bS,4aR,7aS,7bR,8R,9aS)-9a-(Acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one
12-Deoxyphorbol 13-acetate
13-O-Acetylphorbol
NSC 623310
Stillingia Factor S7
Prostratin
CAS Number
60857-08-1
PubChem SID
164232986
PubChem CID
454217

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC P838800 external link Add to cart
PubChem 454217 external link
Data Source Data ID Price
TRC
P838800 external link Add to cart Please log in.
Data Source Data ID
PubChem 454217 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.574634  H Acceptors
H Donor LogD (pH = 5.5) 0.6935895 
LogD (pH = 7.4) 0.69358665  Log P 0.69358957 
Molar Refractivity 103.6662 cm3 Polarizability 40.592663 Å3
Polar Surface Area 104.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - P838800 external link
It is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). Research indicated that prostratin has potential to be useful in the treatment of HIV as it flushes viral reservoirs in latently infecte

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Reuben, et al.: Clin. Cancer Res., 6, 1671 (2000)
  • • Korin, Y., et al.: J. Virol., 76, 8118 (2000)
  • • Wei, X., et al.: Nature, 422, 307 (2000)
  • • Kutsch, O., et al.: Antimicrob. Agents Chemother., 48, 1652 (2000)
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PATENTS

PATENTS

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INTERNET

INTERNET

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