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3604-87-3 molecular structure
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(1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-9-en-8-one

ChemBase ID: 72940
Molecular Formular: C27H44O6
Molecular Mass: 464.63466
Monoisotopic Mass: 464.31378913
SMILES and InChIs

SMILES:
[C@H]1([C@@H](C[C@@H]2[C@](C1)([C@@H]1C(=CC2=O)[C@]2([C@](CC1)([C@H](CC2)[C@@H]([C@@H](CCC(C)(C)O)O)C)C)O)C)O)O
Canonical SMILES:
O[C@@H]([C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)C)CCC(O)(C)C
InChI:
InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1
InChIKey:
UPEZCKBFRMILAV-JMZLNJERSA-N

Cite this record

CBID:72940 http://www.chembase.cn/molecule-72940.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-9-en-8-one
(1R,2R,4S,5R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one
IUPAC Traditional name
ecdysone
Synonyms
Ecdysone
2β,3β,14α,22(R),25-Pentahydroxy-7-cholesten-6-one
α-Ecdysone
2β,3β,14α,22(R),25-五羟基-7-胆甾烯-6-酮
α-蜕皮素
CAS Number
3604-87-3
EC Number
222-760-4
MDL Number
MFCD00042683
Beilstein Number
2422986
PubChem SID
162037860
24894686
PubChem CID
19212
CHEBI ID
16688
CHEMBL
549300
Chemspider ID
18130
Wikipedia Title
Ecdysone

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.507042  H Acceptors
H Donor LogD (pH = 5.5) 1.6912082 
LogD (pH = 7.4) 1.6912079  Log P 1.6912082 
Molar Refractivity 127.4247 cm3 Polarizability 50.48899 Å3
Polar Surface Area 118.22 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
RTECS
FZ8170000 expand Show data source
MSDS Link
Download expand Show data source
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
≥90% expand Show data source
≥99.0% (UV) expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Empirical Formula (Hill Notation)
C27H44O6 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S2294 external link
Research Area: Metabolic Disease
Biological Activity:
Ecdysone is a steroidal prohormone of the major insect molting hormone 20-hydroxyecdysone, which is secreted from the prothoracic glands. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. In Drosophila melanogaster, an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires, and it causes chromosome puffs (sites of high expression) to form. [1]
Sigma Aldrich - 44656 external link
General description
Prothoracic hormone (causes moulting in insects)
Other Notes
Prothorakal gland hormone1

REFERENCES

REFERENCES

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  • • http://en.wikipedia.org/wiki/Ecdysone
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PATENTS

PATENTS

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INTERNET

INTERNET

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