(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: 125296
• Molecular Formular: C27H44O7
• Molecular Mass: 480.63406
• Monoisotopic Mass: 480.30870375
• SMILES: O=C1C=C2[C@@H]([C@]3(C[C@H](O)[C@H](O)C[C@@H]13)C)CC[C@]1([C@@]2(O)CC[C@@H]1C(O)(C)[C@H](O)CCC(O)(C)C)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]2C([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: 20-Hydroxyecdysone; β-Ecdysone; 2β,3β,14α,20β,22,25-Hexahydroxy-7-cholesten-6-one; Ecdysterone; Insect moulting hormone; Polypodine A; 20-Hydroxyecdysone

Database IDs

• CAS Number: 5289-74-7
• MDL Number: MFCD00036740
• Beilstein Number: 1917578
• PubChem SID: 162219646
• PubChem CID: 5459840
• CHEBI ID: 16587
• CHEMBL: 224128
• Chemspider ID: 4573597
• Wikipedia Title: 20-Hydroxyecdysone

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

• Melting Point: 242-244 °C

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Urinary:?%
• Half Life: 4-9 hours
• Metabolism: Hepatic
• Legal Status: Undetermined
• Pregnancy Category: X

Product Information

• Purity: ~85% (UV)
• Empirical Formula (Hill Notation): C27H44O7