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5289-74-7 molecular structure
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(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-9-en-8-one

ChemBase ID: 119450
Molecular Formular: C27H44O7
Molecular Mass: 480.63406
Monoisotopic Mass: 480.30870375
SMILES and InChIs

SMILES:
C12=CC(=O)[C@H]3[C@@]([C@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]([C@@H](CCC(O)(C)C)O)(O)C)O)C)(C[C@@H]([C@@H](C3)O)O)C
Canonical SMILES:
O[C@H]1C[C@@]2(C)[C@@H](C[C@H]1O)C(=O)C=C1[C@@H]2CC[C@]2([C@@]1(O)CC[C@@H]2[C@]([C@@H](CCC(O)(C)C)O)(O)C)C
InChI:
InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1
InChIKey:
NKDFYOWSKOHCCO-YPVLXUMRSA-N

Cite this record

CBID:119450 http://www.chembase.cn/molecule-119450.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-9-en-8-one
IUPAC Traditional name
the-7
Synonyms
Crustecdysone
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one
β-Ecdysone
2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one
Ecdysterone
Insect moulting hormone
Polypodine A
20-Hydroxyecdysone
20-Hydroxyecdysone
CAS Number
5289-74-7
MDL Number
MFCD00036740
Beilstein Number
1917578
PubChem SID
24895674
162103196
PubChem CID
5459840

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.25748  H Acceptors
H Donor LogD (pH = 5.5) 0.6098622 
LogD (pH = 7.4) 0.6098616  Log P 0.6098622 
Molar Refractivity 128.8758 cm3 Polarizability 51.132343 Å3
Polar Surface Area 138.45 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
alcohol: soluble expand Show data source
Apperance
Powder expand Show data source
white to off-white powder expand Show data source
German water hazard class
2 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
Target
Others expand Show data source
Purity
≥93% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - H5142 external link
Biochem/physiol Actions
20-Hydroxyecdysone is an ecdysteroid hormone that plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression involved in molting and metamorphosis. It acts through a heterodimeric receptor comprising the ecdysone receptor and the ultraspiracle proteins (USP).

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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