(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: [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

NAMES AND DATABASE IDS

Names

• 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[8.7.0.0^2,^7.0^1^1,^1^5]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

Database IDs

• CAS Number: 3604-87-3
• EC Number: 222-760-4
• MDL Number: MFCD00042683
• Beilstein Number: 2422986
• PubChem SID: 24894686; 162037860
• PubChem CID: 19212
• CHEBI ID: 16688
• CHEMBL: 549300
• Chemspider ID: 18130
• Wikipedia Title: Ecdysone

CALCULATED PROPERTIES

• Acid pKa: 13.507042
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 1.6912082
• LogD (pH = 7.4): 1.6912079
• Log P: 1.6912082
• Molar Refractivity: 127.4247 cm^3
• Polarizability: 50.48899 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: FZ8170000
• 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: ≥90%; ≥99.0% (UV); 97%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C27H44O6

DETAILS

Selleck Chemicals - S2294

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

General description
Prothoracic hormone (causes moulting in insects)
Other Notes
Prothorakal gland hormone1

REFERENCES

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