(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: 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

NAMES AND DATABASE IDS

Names

• 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[8.7.0.0^2,^7.0^1^1,^1^5]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

Database IDs

• CAS Number: 5289-74-7
• MDL Number: MFCD00036740
• Beilstein Number: 1917578
• PubChem SID: 24895674; 162103196
• PubChem CID: 5459840

CALCULATED PROPERTIES

• Acid pKa: 13.25748
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 0.6098622
• LogD (pH = 7.4): 0.6098616
• Log P: 0.6098622
• Molar Refractivity: 128.8758 cm^3
• Polarizability: 51.132343 Å^3
• Polar Surface Area: 138.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: alcohol: soluble
• Apperance: Powder; white to off-white powder

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥93% (HPLC)
• Salt Data: Free Base
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - H5142

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).